Chesapeake Beach Resort
US$175
/ night
Avg. for September
Select dates to see prices and availability
US$175
/ night
Avg. for September
Monthly average prices
Nightly prices at Chesapeake Beach Resort average US$175 in the cheapest month (September) and US$460 in the most expensive month (March), based on the last 12 months.
| Month | Average price |
|---|---|
| January | US$325 |
| February | US$455 |
| March | US$460 |
| April | US$395 |
| May | US$315 |
| June | US$272 |
| July | US$278 |
| August | US$217 |
| September | US$175 |
| October | US$189 |
| November | US$256 |
| December | US$325 |
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M
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Sept · US$175
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Most expensive: March (~US$460)
Cheapest: September (~US$175)
About this property
Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access and concierge services.
Amenities
Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access and concierge services.
Business amenities
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
Dining
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Rooms
Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
Location
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.7 km) from Lorelei Restaurant & Cabana Bar.
What's nearby
History of Diving Museum(0.6 Miles)
Windley Key Fossil Reef Geological State Park(1.1 Miles)
Islamorada Brewery & Distillery(1.2 Miles)
Lorelei Restaurant & Cabana Bar(1.7 Miles)
Keys History & Discovery Center(1.7 Miles)
Hog Heaven(1.9 Miles)
Matecumbe United Methodist Church(1.9 Miles)
Florida Keys Brewing Co.(2.1 Miles)
MoradaWay Arts & Cultural District(2.2 Miles)
Hurricane Monument(2.3 Miles)
Indian Key Historic State Park(2.9 Miles)
Rain Barrel Village(3.2 Miles)
Founders Park(3.2 Miles)
Islamorada County Park(3.3 Miles)
Bud n' Mary's Dive Center(3.8 Miles)
The preferred airport for Chesapeake Beach Resort is Miami Intl. Airport (MIA)(77.5 Miles)
Parking
Swimming pool
Non-smoking rooms
Housekeeping
Private beach
Beach (nearby)
Location
83409 Overseas Highway, Matecumbe, Islamorada, Florida, United States of America
History of Diving Museum (0.6 Miles)
Windley Key Fossil Reef Geological State Park (1.1 Miles)
Islamorada Brewery & Distillery (1.2 Miles)
Lorelei Restaurant & Cabana Bar (1.7 Miles)
Keys History & Discovery Center (1.7 Miles)
Hog Heaven (1.9 Miles)
Guest reviews
8.8
Fabulous
Based on 1,781 verified reviews
Who stays here?
Business
2%
Couple
46%
Family
36%
Group
11%
Solo
3%
What guests think
AI-generated summary based on recent guest reviews
Across recent reviews, Chesapeake Beach Resort is praised for clean, updated rooms, a scenic oceanfront setting, and a relaxed vibe with pools, a small beach, and included water activities, while service and amenities feel mostly friendly and convenient.
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What guests think
Across recent reviews, Chesapeake Beach Resort is praised for clean, updated rooms, a scenic oceanfront setting, and a relaxed vibe with pools, a small beach, and included water activities, while service and amenities feel mostly friendly and convenient.
Many enjoy the complimentary breakfast with made-to-order omelets and waffles by the water. Recurring downsides include traffic or neighbor noise in some rooms, occasionally loud or weak A/C and other maintenance hiccups, and a shallow, sometimes seaweed-filled shoreline that is less ideal for swimming. Service is generally warm but can be inconsistent, and there is no on-site restaurant and a resort fee applies. Expect a clean, low-key waterfront stay with strong breakfasts and active amenities.
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AI-generated summary based on recent guest reviews
Facilities
Waterfront grounds with two pools, a hot tub, a small private beach, and included kayaks/paddleboards; marina access is a plus. Some found the beach shallow/seaweed and reported occasional maintenance issues, a limited bar, no on-site restaurant, and a resort fee.
Related guest reviews
10
Lia
29 Jun 2025
·
Stayed 1 night
We enjoyed so much staying at this property. The pool and beach area is so beautiful we did not want to go anywhere else. We were also available to use the marina which was a big plus. At check in we were greeted with a champagne glass which was on point. Vanessa at the front desk was super nice and very courteous. Jose at the bar goes above and beyond to serve good drinks. He also made us burgers and hot dogs on Sunday. At breakfast they have a chef making omelets and waffles which were amazing. 5 star! Overall was excellent, the only thing was we felt the double beds are more like twin beds. But after that excellent staff and property. We will definitely be back.
We enjoyed so much staying at this property. The pool and beach area is so beautiful we did not want to go anywhere else. We were also available to use the marina which was a big plus. At check in we were greeted with a champagne glass which was on point. Vanessa at the front desk was super nice and very courteous. Jose at the bar goes above and beyond to serve good drinks. He also made us burgers and hot dogs on Sunday. At breakfast they have a chef making omelets and waffles which were amazing. 5 star! Overall was excellent, the only thing was we felt the double beds are more like twin beds. But after that excellent staff and property. We will definitely be back.
10
CHASE
27 Apr 2025
·
Stayed 3 nights
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
8
Lester
9 Sept 2025
·
Stayed 2 nights
Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
8
Mary
10 May 2024
·
Stayed 1 night
Very nice rooms. Comfortable beds. No restaurant on site but 2 are next door - no need to drive. Great beach. An area to walk out into the ocean with no plant life. Many of the beaches have plant life inside of clear sand. Kayaks and paddle boards to use free. A couple pools. Could use a refresh on the cleanup around the pool more than once a day but very relaxing and quiet. Upstairs units - stairs are wide and not steep. Easy if this would be an issue for you.
Very nice rooms. Comfortable beds. No restaurant on site but 2 are next door - no need to drive. Great beach. An area to walk out into the ocean with no plant life. Many of the beaches have plant life inside of clear sand. Kayaks and paddle boards to use free. A couple pools. Could use a refresh on the cleanup around the pool more than once a day but very relaxing and quiet. Upstairs units - stairs are wide and not steep. Easy if this would be an issue for you.
10
David
3 Aug 2025
·
Stayed 2 nights
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
10
Kim
12 Feb 2025
·
Stayed 3 nights
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
10
Jennifer
14 Feb 2025
·
Stayed 3 nights
A fitness facility would be great!
A fitness facility would be great!
8
Amy
14 Apr 2025
·
Stayed 1 night
I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
8
Donna
15 May 2024
·
Stayed 1 night
Modern room, pools and hot tub. Hot tub wouldn’t turn on. Beach area nice to sit at.
Modern room, pools and hot tub. Hot tub wouldn’t turn on. Beach area nice to sit at.
10
Gregory
13 Sept 2025
·
Stayed 4 nights
Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
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AI-generated summary based on recent guest reviews
Cleanliness
Most guests describe the property and rooms as very clean and well kept. A few noted lapses like debris near pools, dusty or dirty spots, or dogs in the pool area.
Related guest reviews
8
Linda
25 Aug 2025
·
Stayed 1 night
The room given was right by the main road so when you opened door to balcony you could only hear the sounds of the passing cars. Then there was done wall AC unit right about the bed headboard that was blowing hard and there was a thick layer of built up dust over 1 cm thick but when pointed out to front desk nobody could care less. They were not even full my guess is about 20 percent full if that. Other wise a very nice facility that has two pools, private beach and very nice water temp that we were able to really enjoy floating on the kayak
The room given was right by the main road so when you opened door to balcony you could only hear the sounds of the passing cars. Then there was done wall AC unit right about the bed headboard that was blowing hard and there was a thick layer of built up dust over 1 cm thick but when pointed out to front desk nobody could care less. They were not even full my guess is about 20 percent full if that. Other wise a very nice facility that has two pools, private beach and very nice water temp that we were able to really enjoy floating on the kayak
10
Diana
12 Nov 2025
·
Stayed 1 night
Room was extremely clean and well equipped. Robes and slippers were an added bonus. Beautiful nicely kept resort. Pools and beach beautiful. Breakfast was great and Chef Chris seems to love his job. All the staff are great!
Room was extremely clean and well equipped. Robes and slippers were an added bonus. Beautiful nicely kept resort. Pools and beach beautiful. Breakfast was great and Chef Chris seems to love his job. All the staff are great!
10
NICOLA
2 Sept 2025
·
Stayed 1 night
The property was absolutely amazing! Decorated extremely tasteful, immaculate condition, breakfast was lovely sat outside. Would love to return here.
The property was absolutely amazing! Decorated extremely tasteful, immaculate condition, breakfast was lovely sat outside. Would love to return here.
10
Elizabeth
10 Jun 2025
·
Stayed 1 night
Dog poop in pool area Found hair in a lot of the towels used Staff were friendly and dependable
Dog poop in pool area Found hair in a lot of the towels used Staff were friendly and dependable
10
Karen
8 Jan 2025
·
Stayed 1 night
Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.
Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.
6
Anita
26 Jun 2025
·
Stayed 1 night
Older property, rooms could have been cleaner. Beautiful view.
Older property, rooms could have been cleaner. Beautiful view.
10
Brian
12 Apr 2025
·
Stayed 4 nights
The property was clean and and everything was well maintained.
The property was clean and and everything was well maintained.
10
tina
1 Jun 2025
·
Stayed 1 night
One of the pools had a dirty diaper left on a table. The staff dropped off towels but didn't look around to clean up left over cups, used diaper, etc. Granted guests should be responsible and clean up their own trash but it would be nice if the housekeeping would watch for this since I had to point it out. Other than that it was a great location and nice hotel. Two restaurants next door to the property so you don't have to drive if you don't want. Breakfast was great, made to order custom omelet, rooms had robes and slippers, there's paddle boards, clear bottom kayaks and fishing poles to use.
One of the pools had a dirty diaper left on a table. The staff dropped off towels but didn't look around to clean up left over cups, used diaper, etc. Granted guests should be responsible and clean up their own trash but it would be nice if the housekeeping would watch for this since I had to point it out. Other than that it was a great location and nice hotel. Two restaurants next door to the property so you don't have to drive if you don't want. Breakfast was great, made to order custom omelet, rooms had robes and slippers, there's paddle boards, clear bottom kayaks and fishing poles to use.
2
leslie
27 May 2025
·
Stayed 1 night
Dirty property not wonderful as Expedia rated . People had their dogs swimming in the pool staff did nothing about it and claimed they had no complaints . Felt like I was in a third world country not Islamorada . Shame on you Expedia for not allowing me to cancel my reservation & blaming me for contacting to late . Will never use you again or go to this disgusting hotel ! Beware is my word of caution to anyone considering this property or Expedia .
Dirty property not wonderful as Expedia rated . People had their dogs swimming in the pool staff did nothing about it and claimed they had no complaints . Felt like I was in a third world country not Islamorada . Shame on you Expedia for not allowing me to cancel my reservation & blaming me for contacting to late . Will never use you again or go to this disgusting hotel ! Beware is my word of caution to anyone considering this property or Expedia .
10
Ann
20 May 2025
·
Stayed 1 night
Beautiful and extremely clean property. The grounds were perfect and our room was stunning!
Beautiful and extremely clean property. The grounds were perfect and our room was stunning!
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AI-generated summary based on recent guest reviews
Rooms
Renovated, modern rooms with comfortable beds and great ocean views; villas feel spacious, but some bathrooms are small with limited storage. Multiple guests reported traffic or neighbor noise, plus loud or weak A/C and occasional water-pressure problems.
Related guest reviews
8
valerie
30 Mar 2025
·
Stayed 5 nights
The view from my room was awesome. The public areas (to beach, pools, breakfast) were extremely convenient to get to. The only negative comment I have concerns the room amenities. There should be a dresser for more drawer space and a few more hooks or racks in bathroom for towels. Other than that it was a fantastic resort that I would highly recommend
The view from my room was awesome. The public areas (to beach, pools, breakfast) were extremely convenient to get to. The only negative comment I have concerns the room amenities. There should be a dresser for more drawer space and a few more hooks or racks in bathroom for towels. Other than that it was a fantastic resort that I would highly recommend
6
Bailey
27 May 2024
·
Stayed 3 nights
Would rate it a 7.8 out of 10. The facilities were great. Was put right next to an ice machine on the bottom floor, if you have a room above you, not worth it at all. Sounded like a stampede every morning at 5 and at night till 12. No sleep.
Would rate it a 7.8 out of 10. The facilities were great. Was put right next to an ice machine on the bottom floor, if you have a room above you, not worth it at all. Sounded like a stampede every morning at 5 and at night till 12. No sleep.
10
Rolf
18 Jul 2024
·
Stayed 2 nights
We loved the location, the spaciousness of the room, and the resort activities that were included in our stay. The AC in our room was very loud though, even on the lowest level, so much that it was hard to sleep with it on. Overall however, we enjoyed our stay at Chesapeake Beach Resort.
We loved the location, the spaciousness of the room, and the resort activities that were included in our stay. The AC in our room was very loud though, even on the lowest level, so much that it was hard to sleep with it on. Overall however, we enjoyed our stay at Chesapeake Beach Resort.
8
Lester
9 Sept 2025
·
Stayed 2 nights
Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
8
Shelly
6 Jul 2025
·
Stayed 2 nights
The property is nice. Water pressure was not great. Water stopped completely while in the shower on multiple occasions. It was not off long but it was completely off. It was nice that breakfast was served a bit later, but even by 9 some things were gone. Overall nice stay.
The property is nice. Water pressure was not great. Water stopped completely while in the shower on multiple occasions. It was not off long but it was completely off. It was nice that breakfast was served a bit later, but even by 9 some things were gone. Overall nice stay.
6
Michael
3 Jul 2025
·
Stayed 3 nights
Property was nice enough. Its not a resort. Did have issue fold out couch. No mattresses. Springs only. Need to be cleaned and repaced . All in all i would return.
Property was nice enough. Its not a resort. Did have issue fold out couch. No mattresses. Springs only. Need to be cleaned and repaced . All in all i would return.
10
Adrian
4 Aug 2025
·
Stayed 2 nights
The room was a little hot but overall everything was good
The room was a little hot but overall everything was good
10
Chester
24 Aug 2025
·
Stayed 3 nights
Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!
Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!
10
Ernesto
16 May 2025
·
Stayed 2 nights
Everything was amazing just the a/c was not cold enough it gets warm even with fan on
Everything was amazing just the a/c was not cold enough it gets warm even with fan on
10
Gregory
13 Sept 2025
·
Stayed 4 nights
Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
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AI-generated summary based on recent guest reviews
Service
Service is generally friendly and accommodating, with helpful front desk staff and quick follow-ups. Experiences vary, with reports of slow or unhelpful responses and occasional rudeness at breakfast.
Related guest reviews
8
Ashley
19 May 2025
·
Stayed 1 night
Our stay at Chesapeake was absolutely phenomenal. The property itself is stunning—immaculately kept grounds, lush and peaceful, with a sense of tranquility that instantly helps you unwind. Everything was clean and thoughtfully maintained, from the pathways to the landscaping, which truly stood out. The room was comfortable and inviting. The air conditioning kept things perfectly cool, though it was a bit on the louder side during the night. One small detail we noticed was the smoke detector’s green light, which was brighter than expected and occasionally disrupted our sleep, even with the excellent blackout curtains. Still, these are minor notes in an otherwise serene experience. Check-in was smooth and friendly, though for added privacy, I personally prefer when room numbers aren’t spoken aloud. That said, the agent was warm and welcoming. Overall, Chesapeake offered an incredibly restful and beautiful experience. We deeply appreciated the peaceful atmosphere and how cared-for every inch of the property felt. We look forward to returning!
Our stay at Chesapeake was absolutely phenomenal. The property itself is stunning—immaculately kept grounds, lush and peaceful, with a sense of tranquility that instantly helps you unwind. Everything was clean and thoughtfully maintained, from the pathways to the landscaping, which truly stood out. The room was comfortable and inviting. The air conditioning kept things perfectly cool, though it was a bit on the louder side during the night. One small detail we noticed was the smoke detector’s green light, which was brighter than expected and occasionally disrupted our sleep, even with the excellent blackout curtains. Still, these are minor notes in an otherwise serene experience. Check-in was smooth and friendly, though for added privacy, I personally prefer when room numbers aren’t spoken aloud. That said, the agent was warm and welcoming. Overall, Chesapeake offered an incredibly restful and beautiful experience. We deeply appreciated the peaceful atmosphere and how cared-for every inch of the property felt. We look forward to returning!
4
Cecilia
15 Jun 2025
·
Stayed 1 night
We unfortunately found your resort lacking in good customer service. No one at the pools or beach to offer towels or to open an umbrella. Breakfast was mediocre at best, the coffee not that good, the cook was super angry looking and not courteous AT ALL. The AC in the rooms very annoying-antiquated. We were promised we could stay until 12, then the front desk changes their mind. NOT WORTH THE MONEY. 2 Stars at best.
We unfortunately found your resort lacking in good customer service. No one at the pools or beach to offer towels or to open an umbrella. Breakfast was mediocre at best, the coffee not that good, the cook was super angry looking and not courteous AT ALL. The AC in the rooms very annoying-antiquated. We were promised we could stay until 12, then the front desk changes their mind. NOT WORTH THE MONEY. 2 Stars at best.
6
Adel
6 Apr 2025
·
Stayed 2 nights
The chef at the breakfast was so rude and hostile When I complained to the front desk (Venessa she did not care even I told her he yelled at me in front of other guests. Venessa and that breakfast chef are very unprofessional hence I will never go there again On the other hand, another person at the reception was very kind and professional and her name is Adriana
The chef at the breakfast was so rude and hostile When I complained to the front desk (Venessa she did not care even I told her he yelled at me in front of other guests. Venessa and that breakfast chef are very unprofessional hence I will never go there again On the other hand, another person at the reception was very kind and professional and her name is Adriana
10
cheryl
13 Feb 2025
·
Stayed 4 nights
I love this place, every stay is truly a wonderful experience. The staff is always helpful and friendly. The grounds are really pretty as well.
I love this place, every stay is truly a wonderful experience. The staff is always helpful and friendly. The grounds are really pretty as well.
10
Judy
11 Aug 2025
·
Stayed 1 night
Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!
Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!
10
robert
24 Nov 2024
·
Stayed 3 nights
The staff was exceptional throughout the whole proerty. I will stay again.
The staff was exceptional throughout the whole proerty. I will stay again.
2
Amanda
29 May 2025
·
Stayed 3 nights
I had a terrible experience at Chesapeake Beach Resort. I stayed for three nights, but for the first two, I couldn’t sleep because the air conditioning was leaking water directly onto the bed. I reported the problem to the front desk on the first day, and they told me they would send maintenance, but nothing was done. They also said I should call Expedia to resolve the issue, which I did, but no one helped me, and my requests were completely ignored. They finally changed my room on the last night, but the damage was already done. I also requested a refund for the first two nights, and I’m still waiting for the security deposit to be returned. This situation was handled very poorly, and I wouldn’t recommend this hotel to anyone. It was a stressful and disappointing experience.
I had a terrible experience at Chesapeake Beach Resort. I stayed for three nights, but for the first two, I couldn’t sleep because the air conditioning was leaking water directly onto the bed. I reported the problem to the front desk on the first day, and they told me they would send maintenance, but nothing was done. They also said I should call Expedia to resolve the issue, which I did, but no one helped me, and my requests were completely ignored. They finally changed my room on the last night, but the damage was already done. I also requested a refund for the first two nights, and I’m still waiting for the security deposit to be returned. This situation was handled very poorly, and I wouldn’t recommend this hotel to anyone. It was a stressful and disappointing experience.
10
Melissa R
12 Oct 2025
·
Stayed 1 night
Check in person was very friendly and included a glass of champagne! Beautiful resort location!
Check in person was very friendly and included a glass of champagne! Beautiful resort location!
10
Edson
17 Feb 2025
·
Stayed 1 night
The staff was amazing! When my wife forgot her phone, Vanessa immediately took action after I explained the situation. She quickly located the phone and arranged for it to be shipped to our home. Her prompt and helpful response made all the difference. We will definitely stay here again!
The staff was amazing! When my wife forgot her phone, Vanessa immediately took action after I explained the situation. She quickly located the phone and arranged for it to be shipped to our home. Her prompt and helpful response made all the difference. We will definitely stay here again!
10
Joseph
6 Dec 2024
·
Stayed 7 nights
Chesapeake Beach Resort is an excellent choice for family vacation or couple’s gate-away. This was our second time staying at the resort. This time we brought our kids and they absolutely loved it here. The exclusiveness, the private beach, water activities, two pools, and courteous resort staff. My family was welcomed warmly by Charlsie. Charlsie made my family feel welcomed and granted my wife’s request and upgraded us to a villa facing the ocean. This trip was my wife’s 40th birthday and Charlsie made it extra special for our family. I want to take this time to thank all the staff of Chesapeake Resort. The front desk staff, the grounds keep, the breakfast crew and their engagements with the kids, and the housekeeping crew. All pleasant staff. Thank you.
Chesapeake Beach Resort is an excellent choice for family vacation or couple’s gate-away. This was our second time staying at the resort. This time we brought our kids and they absolutely loved it here. The exclusiveness, the private beach, water activities, two pools, and courteous resort staff. My family was welcomed warmly by Charlsie. Charlsie made my family feel welcomed and granted my wife’s request and upgraded us to a villa facing the ocean. This trip was my wife’s 40th birthday and Charlsie made it extra special for our family. I want to take this time to thank all the staff of Chesapeake Resort. The front desk staff, the grounds keep, the breakfast crew and their engagements with the kids, and the housekeeping crew. All pleasant staff. Thank you.
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AI-generated summary based on recent guest reviews
Location
Oceanfront Islamorada location with easy access to restaurants, marina trips, and the rest of the Keys. Rooms near the highway can pick up traffic noise.
Related guest reviews
10
Taryn
13 May 2024
·
Stayed 4 nights
This was my first time in the Keys and this hotel did not disappoint. The property is beautiful, staff is super friendly and helpful and the location is perfect if you’re planning on checking out other islands. Islamorada is just under 2 hours from Key West so it’s easily drivable. I would absolutely stay here again.
This was my first time in the Keys and this hotel did not disappoint. The property is beautiful, staff is super friendly and helpful and the location is perfect if you’re planning on checking out other islands. Islamorada is just under 2 hours from Key West so it’s easily drivable. I would absolutely stay here again.
8
Kerry
7 Aug 2025
·
Stayed 4 nights
The Chesapeake Beach Resort was lovely. It is a small, clean, picturesque resort. We had the beautiful beach area with pool towels and lounge chairs to ourselves. We were surprised and excited about the 2 free hours of either paddle boarding, kayaking, or fishing poles per day. The free breakfast omelette station was delicious. The front desk sells frozen shrimp for fishing. A tour to the sandbar is a must! Unfortunately we booked a different tour before check in, but saw a cheaper tiki boat tour to the sandbar at the hotel. All in all, great stay with nice beach area! Would recommend!
The Chesapeake Beach Resort was lovely. It is a small, clean, picturesque resort. We had the beautiful beach area with pool towels and lounge chairs to ourselves. We were surprised and excited about the 2 free hours of either paddle boarding, kayaking, or fishing poles per day. The free breakfast omelette station was delicious. The front desk sells frozen shrimp for fishing. A tour to the sandbar is a must! Unfortunately we booked a different tour before check in, but saw a cheaper tiki boat tour to the sandbar at the hotel. All in all, great stay with nice beach area! Would recommend!
10
Kirstin
18 Apr 2025
·
Stayed 4 nights
Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation .
Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation .
10
yumi
19 Jul 2025
·
Stayed 2 nights
Nice hotel, friendly staff. Clean, safe. Good amenities. The free breakfast is nice. A little close to the highway, so you can hear the traffic noise depending on your room location. But all in all, a good place to stay
Nice hotel, friendly staff. Clean, safe. Good amenities. The free breakfast is nice. A little close to the highway, so you can hear the traffic noise depending on your room location. But all in all, a good place to stay
10
scott
4 Feb 2025
·
Stayed 1 night
Great location, staff was great, complementary breakfast was very good. We definitely will stay here again.
Great location, staff was great, complementary breakfast was very good. We definitely will stay here again.
10
Michael
22 Jul 2025
·
Stayed 4 nights
We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
8
Bruce
3 May 2024
·
Stayed 3 nights
The rooms were very nice, recently updated and very clean. The staff are very helpful. In order to minimize the noise, you should ask for an oceanfront room. Anything near route one is noisy, and there is nothing you can do about accepted distance yourself from there.
The rooms were very nice, recently updated and very clean. The staff are very helpful. In order to minimize the noise, you should ask for an oceanfront room. Anything near route one is noisy, and there is nothing you can do about accepted distance yourself from there.
8
Kurt
19 Apr 2025
·
Stayed 1 night
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
10
tracy
14 Feb 2025
·
Stayed 1 night
Great location nearby restaurants. Riim was very clean beds wete great as was the staff
Great location nearby restaurants. Riim was very clean beds wete great as was the staff
10
Pablo
26 Jun 2025
·
Stayed 1 night
It was excellent. Beautiful location, friendly and helpful staff, amazing views.
It was excellent. Beautiful location, friendly and helpful staff, amazing views.
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AI-generated summary based on recent guest reviews
Dining
Complimentary breakfast is a highlight for many, thanks to made-to-order omelets/waffles and seaside seating. Feedback varies at times, with occasional shortages, limited indoor seating in bad weather, and no full on-site restaurant.
Related guest reviews
8
vickie
28 Jul 2025
·
Stayed 1 night
Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho
Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho
6
Lorie
22 Jan 2025
·
Stayed 2 nights
great stay, beautiful resort. AC didn’t work the best, didn’t love the barn door that didn’t lock in bathroom. Breakfast was great, but no indoor seating. One day was cool and rainy and no where to sit and eat. Pool and hot was nice
great stay, beautiful resort. AC didn’t work the best, didn’t love the barn door that didn’t lock in bathroom. Breakfast was great, but no indoor seating. One day was cool and rainy and no where to sit and eat. Pool and hot was nice
4
Cecilia
15 Jun 2025
·
Stayed 1 night
We unfortunately found your resort lacking in good customer service. No one at the pools or beach to offer towels or to open an umbrella. Breakfast was mediocre at best, the coffee not that good, the cook was super angry looking and not courteous AT ALL. The AC in the rooms very annoying-antiquated. We were promised we could stay until 12, then the front desk changes their mind. NOT WORTH THE MONEY. 2 Stars at best.
We unfortunately found your resort lacking in good customer service. No one at the pools or beach to offer towels or to open an umbrella. Breakfast was mediocre at best, the coffee not that good, the cook was super angry looking and not courteous AT ALL. The AC in the rooms very annoying-antiquated. We were promised we could stay until 12, then the front desk changes their mind. NOT WORTH THE MONEY. 2 Stars at best.
10
David
3 Aug 2025
·
Stayed 2 nights
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
10
Kim
12 Feb 2025
·
Stayed 3 nights
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
10
Francisco
30 Jul 2025
·
Stayed 1 night
Best breakfast ever right on the ocean 😋
Best breakfast ever right on the ocean 😋
8
Amy
14 Apr 2025
·
Stayed 1 night
I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
8
GEORGE
5 Jun 2024
·
Stayed 3 nights
Really great resort. Everything renovated or new. Amazing views. Everything clean and room service impeccable. Very attentive to our needs and great communication from front desk. Staff not as friendly as it could be, especially at breakfast. Felt like getting breakfast somewhere else. Also, a lot of empty cans and empty wrappers around the property. Not a big deal but it could be better especially so close to the sea. Obviously people throwing stuff around not great but staff can walk around and clean a bit. Internet was not working well and then towards our stay it wasn't working at all. Internet has to be available and solid especially for people that might need to connect a bit.
Really great resort. Everything renovated or new. Amazing views. Everything clean and room service impeccable. Very attentive to our needs and great communication from front desk. Staff not as friendly as it could be, especially at breakfast. Felt like getting breakfast somewhere else. Also, a lot of empty cans and empty wrappers around the property. Not a big deal but it could be better especially so close to the sea. Obviously people throwing stuff around not great but staff can walk around and clean a bit. Internet was not working well and then towards our stay it wasn't working at all. Internet has to be available and solid especially for people that might need to connect a bit.
10
Deepak
3 Feb 2025
·
Expedia’s pictures don’t do justice to beauty of this property. While the room was small, Walls are thin, could hear noises from neighboring rooms. Bathroom was upgraded. However, vibe of the resort and calmness triumpj over all the petty issues. The entire resort has a wonderful vibe, and the beachfront views are breathtaking. The breakfast was fantastic, and the staff were exceptional. I only wish we could have stayed longer! There are plenty of restaurants with different kinds of cuisines in such a small area.
Expedia’s pictures don’t do justice to beauty of this property. While the room was small, Walls are thin, could hear noises from neighboring rooms. Bathroom was upgraded. However, vibe of the resort and calmness triumpj over all the petty issues. The entire resort has a wonderful vibe, and the beachfront views are breathtaking. The breakfast was fantastic, and the staff were exceptional. I only wish we could have stayed longer! There are plenty of restaurants with different kinds of cuisines in such a small area.
10
Jorge
17 Feb 2025
·
Stayed 3 nights
The hotel is in great condition, very clean and the staff is amazing! The breakfast is a game changer! There's an omelet station!!! Pools were nice and the fact we could bring our boat made it perfect. Couple restaurants close by also great!
The hotel is in great condition, very clean and the staff is amazing! The breakfast is a game changer! There's an omelet station!!! Pools were nice and the fact we could bring our boat made it perfect. Couple restaurants close by also great!
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AI-generated summary based on recent guest reviews
10
Debrah
3 weeks ago
·
Stayed 3 nights
Beautiful property and great little breakfast!!
Beautiful property and great little breakfast!!
10
Janet
3 weeks ago
·
Stayed 3 nights
Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them ..
Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them ..
8
Cheryl
3 weeks ago
·
Stayed 1 night
We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after.
We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after.
10
Dawn
3 weeks ago
·
Stayed 2 nights
Great place to stay, good location to restaurants and activities. Nice pool with tiki bar that mix a good drink. Full breakfast with made to order eggs and omelets which was a nice change from the normal continental breakfast. Stayed by the pool because Beach was full of sargassum but they work hard to clean it. Not much swimming room in the ocean…again a lot of seaweed.
Great place to stay, good location to restaurants and activities. Nice pool with tiki bar that mix a good drink. Full breakfast with made to order eggs and omelets which was a nice change from the normal continental breakfast. Stayed by the pool because Beach was full of sargassum but they work hard to clean it. Not much swimming room in the ocean…again a lot of seaweed.
10
Jamie
3 weeks ago
·
Stayed 2 nights
The staff was excellent and the amenities were very convenient
The staff was excellent and the amenities were very convenient
FAQs about Chesapeake Beach Resort
Is parking available at the property?
Parking is available on-site and is free. However, it is limited, so guests are encouraged to arrive early.
What type of breakfast is offered and what are the serving hours?
A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Does the property allow pets?
Pets are allowed at the property with a pet fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees.
What are the standard check-in and check-out times?
Check-in time is at 4:00 PM and check-out time is at 11:00 AM. Early check-in and late check-out may be available upon request and may incur additional charges.
What accessibility features are available for guests with disabilities?
The property offers limited wheelchair accessibility, including accessible parking and public areas. Guests are encouraged to contact the property for specific needs.
What is the location of the property in relation to key landmarks?
Chesapeake Beach Resort is located in Islamorada (Matecumbe), within a 5-minute drive of the History of Diving Museum and Windley Key Fossil Reef Geological State Park. It is approximately 1.2 miles from Islamorada Brewery & Distillery and 1.7 miles from Keys History & Discovery Center.
Does the property have a swimming pool?
Yes, the property features two outdoor pools, including a heated pool. Pool access is available from 8:00 AM to 6:00 PM.
What are the policies for guests staying with children?
Children are welcome at the property. There is no minimum age requirement for children to stay for free.
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Prices for upcoming dates
September 2026
Su | Mo | Tu | We | Th | Fr | Sa |
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October 2026
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Cheaper
Pricier
Average nightly price across deals, with taxes & fees.
Prices in USD for 2 guests, updated daily.
- 2026-09-15: NO DATA
- 2026-09-16: 207.06809155000303USD
- 2026-09-17: 209.94164872186278USD
- 2026-09-18: 256.2246373957214USD
- 2026-09-19: 280.61563144627377USD
- 2026-09-20: 212.92827195976255USD
- 2026-09-21: 212.72604140266418USD
- 2026-09-22: 235.6594265918884USD
- 2026-09-23: 219.61560878913878USD
- 2026-09-24: 217.3935543415222USD
- 2026-09-25: 273.69830795983887USD
- 2026-09-26: 270.98676404107664USD
- 2026-09-27: 212.64030902288818USD
- 2026-09-28: 219.5576325093231USD
- 2026-09-29: 212.64030902288818USD
- 2026-09-30: 217.3935543415222USD
- 2026-10-01: 215.44307669947813USD
- 2026-10-02: 275.57790810375974USD
- 2026-10-03: 295.61327132788085USD
- 2026-10-04: 246.65372866976927USD
- 2026-10-05: 217.10131446597288USD
- 2026-10-06: 217.3935543415222USD
- 2026-10-07: 215.95727737185666USD
- 2026-10-08: 219.5576325093231USD
- 2026-10-09: 417.3263217366638USD
- 2026-10-10: 417.4808899483642USD
- 2026-10-11: 246.65372866976927USD
- 2026-10-12: 218.7595698330383USD
- 2026-10-13: 244.58626003442382USD
- 2026-10-14: 217.10131446597288USD
- 2026-10-15: 246.65372866976927USD
- 2026-10-16: 263.019214502243USD
- 2026-10-17: 393.2311404775085USD
- 2026-10-18: 208.13730861816404USD
- 2026-10-19: 213.53809653263855USD
- 2026-10-20: 377.7674198837585USD
- 2026-10-21: 208.13730861816404USD
- 2026-10-22: 371.936984438446USD
- 2026-10-23: 265.4752509364624USD
- 2026-10-24: 408.81007440692133USD
- 2026-10-25: 243.76832631384275USD
- 2026-10-26: 220.5685740879669USD
- 2026-10-27: 236.80627977731322USD
- 2026-10-28: 213.53809653263855USD
- 2026-10-29: 220.5685740879669USD
- 2026-10-30: 399.247121138916USD
- 2026-10-31: 411.52996099618525USD
- 2026-11-01: 236.80627977731322USD
- 2026-11-02: 227.24329130816648USD
- 2026-11-03: 213.9212257551727USD
- 2026-11-04: 379.71735190811154USD
- 2026-11-05: 351.4721672897644USD
- 2026-11-06: 411.52996099618525USD
- 2026-11-07: 450.69897500741575USD
- 2026-11-08: 236.80627977731322USD
- 2026-11-09: 362.38561234594727USD
- 2026-11-10: 217.7002970873108USD
- 2026-11-11: 351.4721672897644USD
- 2026-11-12: 213.53809653263855USD
- 2026-11-13: 315.6558155848388USD
- 2026-11-14: 332.3561874756164USD
- 2026-11-15: 213.9212257551727USD
Front desk staff will greet guests on arrival at the property. Information provided by the property may be translated using automated translation tools.
Check-in must be done by someone who is at least 18 years old.
- Extra-person charges may apply and vary depending on property policy
- Government-issued photo identification and a credit card may be required at check-in for incidental charges
- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
- This property accepts credit cards; cash is not accepted
- Safety features at this property include a fire extinguisher
- This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
- Pool access available from 8:00 AM to 6:00 PM.
- Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
- Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
- Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation (surcharges apply and can be found in the Fees section).
- Contactless check-in and contactless check-out are available.
- Pet deposit: USD 50.00 per night
- Pet fee: USD 50.00 per accommodation, per night
- Service animals are exempt from fees
- A late check-out fee will be charged
The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.
Popular amenities
Parking
Swimming pool
Non-smoking rooms
Housekeeping
Private beach
Beach (nearby)
Activities
Swimming pool
Private beach
Beach (nearby)
Fishing
Pool outdoor
Outdoor heated pool
Live music
Outdoor Furniture
Pool (Seasonal Outdoor)
Parking
Parking
Free parking
Parking (Limited)
Parking Onsite
General
Non-smoking rooms
Allergy-free room available
Beach Sun Loungers
Fence Around Pool
Snack Bar/Deli
Wheelchair Accessible (Limited)
Services
Housekeeping
Luggage storage
24-Hour Front Desk
Concierge Services
Internet
Free wi-fi