Name: Chesapeake Beach Resort
Address: 83409 Overseas Highway, Matecumbe, Islamorada, Florida, United States of America, Islamorada, Upper Matecumbe Key, US
Price range: $204–$426 per night
Rating: 8.75

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.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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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

Jun 29, 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.

10

CHASE

Apr 27, 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

8

Lester

Sep 9, 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.

8

Mary

May 10, 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.

10

David

Aug 3, 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

10

Kim

Feb 12, 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.

10

Jennifer

Feb 14, 2025

·

Stayed 3 nights

A fitness facility would be great!

8

Amy

Apr 14, 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.

8

Donna

May 15, 2024

·

Stayed 1 night

Modern room, pools and hot tub. Hot tub wouldn’t turn on. Beach area nice to sit at.

10

Gregory

Sep 13, 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.

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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

Aug 25, 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

10

Diana

Nov 12, 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!

10

NICOLA

Sep 2, 2025

·

Stayed 1 night

The property was absolutely amazing! Decorated extremely tasteful, immaculate condition, breakfast was lovely sat outside. Would love to return here.

10

Elizabeth

Jun 10, 2025

·

Stayed 1 night

Dog poop in pool area Found hair in a lot of the towels used Staff were friendly and dependable

10

Karen

Jan 8, 2025

·

Stayed 1 night

Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.

6

Anita

Jun 26, 2025

·

Stayed 1 night

Older property, rooms could have been cleaner. Beautiful view.

10

Brian

Apr 12, 2025

·

Stayed 4 nights

The property was clean and and everything was well maintained.

10

tina

Jun 1, 2025

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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.

2

leslie

May 27, 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 .

10

Ann

May 20, 2025

·

Stayed 1 night

Beautiful and extremely clean property. The grounds were perfect and our room was stunning!

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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

Mar 30, 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

6

Bailey

May 27, 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.

10

Rolf

Jul 18, 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.

8

Lester

Sep 9, 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.

8

Shelly

Jul 6, 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.

6

Michael

Jul 3, 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.

10

Adrian

Aug 4, 2025

·

Stayed 2 nights

The room was a little hot but overall everything was good

10

Chester

Aug 24, 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!!

10

Ernesto

May 16, 2025

·

Stayed 2 nights

Everything was amazing just the a/c was not cold enough it gets warm even with fan on

10

Gregory

Sep 13, 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.

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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

May 19, 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!

4

Cecilia

Jun 15, 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.

6

Adel

Apr 6, 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

10

cheryl

Feb 13, 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.

10

Judy

Aug 11, 2025

·

Stayed 1 night

Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!

10

robert

Nov 24, 2024

·

Stayed 3 nights

The staff was exceptional throughout the whole proerty. I will stay again.

2

Amanda

May 29, 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.

10

Melissa R

Oct 12, 2025

·

Stayed 1 night

Check in person was very friendly and included a glass of champagne! Beautiful resort location!

10

Edson

Feb 17, 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!

10

Joseph

Dec 6, 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.

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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

May 13, 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.

8

Kerry

Aug 7, 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!

10

Kirstin

Apr 18, 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 .

10

yumi

Jul 19, 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

10

scott

Feb 4, 2025

·

Stayed 1 night

Great location, staff was great, complementary breakfast was very good. We definitely will stay here again.

10

Michael

Jul 22, 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!

8

Bruce

May 3, 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.

8

Kurt

Apr 19, 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.

10

tracy

Feb 14, 2025

·

Stayed 1 night

Great location nearby restaurants. Riim was very clean beds wete great as was the staff

10

Pablo

Jun 26, 2025

·

Stayed 1 night

It was excellent. Beautiful location, friendly and helpful staff, amazing views.

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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

Jul 28, 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

6

Lorie

Jan 22, 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

4

Cecilia

Jun 15, 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.

10

David

Aug 3, 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

10

Kim

Feb 12, 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.

10

Francisco

Jul 30, 2025

·

Stayed 1 night

Best breakfast ever right on the ocean 😋

8

Amy

Apr 14, 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.

8

GEORGE

Jun 5, 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.

10

Deepak

Feb 3, 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.

10

Jorge

Feb 17, 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!

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AI-generated summary based on recent guest reviews

Month	Average price
January	$325
February	$455
March	$460
April	$395
May	$315
June	$272
July	$278
August	$217
September	$175
October	$189
November	$256
December	$325

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14 $208	15 $204	16 $206	17 $211	18 $257	19 $393
20 $211	21 $213	22 $234	23 $219	24 $215	25 $273	26 $278
27 $217	28 $219	29 $219	30 $217

Su	Mo	Tu	We	Th	Fr	Sa
				1 $217	2 $278	3 $426
4 $246	5 $220	6 $217	7 $216	8 $219	9 $417	10 $417
11 $245	12 $215	13 $244	14 $214	15 $235	16 $261	17 $290
18 $206	19 $215	20 $246	21 $206	22 $368	23 $263	24 $409
25 $253	26 $223	27 $235	28 $221	29 $222	30 $282	31 $324

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About this property

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