Winslow's Bungalows - Key West Historic Inns
US$310
/ night
Avg. for November
Prices for Winslow's Bungalows - Key West Historic Inns
Select dates to see prices and availability
US$310
/ night
Avg. for November
Monthly average prices
Nightly prices at Winslow's Bungalows - Key West Historic Inns average US$172 in the cheapest month (September) and US$544 in the most expensive month (February), based on the last 12 months.
| Month | Average price |
|---|---|
| January | US$453 |
| February | US$544 |
| March | US$524 |
| April | US$423 |
| May | US$343 |
| June | US$249 |
| July | US$253 |
| August | US$189 |
| September | US$172 |
| October | US$293 |
| November | US$310 |
| December | US$363 |
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Nov · US$310
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Most expensive: February (~US$544)
Cheapest: September (~US$172)
About this property
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and concierge services.
Amenities
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and concierge services.
Business amenities
Featured amenities include luggage storage, coffee/tea in a common area, and microwave in a common area. Self parking (subject to charges) is available onsite.
Dining
Satisfy your appetite with American cuisine at Bungalow Bar, a poolside bar/lounge which features a garden view. Wrap up your day with a drink at the poolside bar. Continental breakfasts are available daily from 8:00 AM to 10:00 AM for a fee.
Rooms
Stay in one of 85 guestrooms featuring LED televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have designer toiletries and hair dryers. Conveniences include safes and ceiling fans, as well as phones with free local calls.
Location
With a stay at Winslow's Bungalows - Key West Historic Inns, you'll be centrally located in Key West, just a 5-minute walk from Duval Street and 10 minutes by foot from Florida Keys Beaches. This hotel is 0.4 mi (0.6 km) from Ernest Hemingway Home and Museum and 0.7 mi (1.1 km) from Southernmost Point.
What's nearby
Saint Mary Star of the Sea(0.2 Miles)
Tennessee Williams Key West Exhibit(0.2 Miles)
Duval Street(0.2 Miles)
Key West Cemetery(0.3 Miles)
Key West Firehouse Museum(0.3 Miles)
City Zoo Gallery(0.3 Miles)
Key West Lighthouse and Keeper's Quarters Museum(0.4 Miles)
Ernest Hemingway Home and Museum(0.4 Miles)
The Kite House(0.4 Miles)
Florida Keys Beaches(0.5 Miles)
Key West Butterfly and Nature Conservatory(0.6 Miles)
Simonton Beach(0.6 Miles)
South Beach(0.6 Miles)
Donkey Milk House(0.6 Miles)
The Unitarian Universalist Fellowship of Key West(0.6 Miles)
The preferred airport for Winslow's Bungalows - Key West Historic Inns is Key West Intl. Airport (EYW)(3.3 Miles)
Parking
Swimming pool
Non-smoking rooms
Tour desk
Housekeeping
Safe-deposit box
Location
725 Truman Avenue, Old Town Key West, Key West, Florida, United States of America
Saint Mary Star of the Sea (0.2 Miles)
Tennessee Williams Key West Exhibit (0.2 Miles)
Duval Street (0.2 Miles)
Key West Cemetery (0.3 Miles)
Key West Firehouse Museum (0.3 Miles)
City Zoo Gallery (0.3 Miles)
Room options
5
King Suite with Sofa Bed
Room details
1 Extra-Large Double Bed
and 1 Sofa Bed
Sleeps 3
500 ft²
Air ConditioningHeatingWi-Fi (Free)Patio
4
Single Queen
Room details
1 Large Double Bed
Sleeps 2
240 ft²
Air ConditioningHeatingWi-Fi (Free)
6
Classic King
Room details
1 Extra-Large Double Bed
Sleeps 2
240 ft²
Air ConditioningHeatingWi-Fi (Free)
7
Annex King Mobility
Room details
1 Extra-Large Double Bed
Sleeps 2
312 ft²
Air ConditioningHeatingWi-Fi (Free)
5
Premier King with Patio Or Balcony
Room details
1 Extra-Large Double Bed
Sleeps 2
180 ft²
Air ConditioningHeatingWi-Fi (Free)Patio
6
Bungalow King
Room details
1 Extra-Large Double Bed
Sleeps 2
240 ft²
Air ConditioningHeatingWi-Fi (Free)
4
Treehouse King Suite
Room details
1 Extra-Large Double Bed
Sleeps 2
425 ft²
Air ConditioningHeatingWi-Fi (Free)Patio
4
King Mobility
Room details
1 Extra-Large Double Bed
Sleeps 2
312 ft²
Air ConditioningHeatingWi-Fi (Free)Patio
5
King Suite with Soaking Tub
Room details
1 Extra-Large Double Bed
Sleeps 2
400 ft²
Air ConditioningHeatingWi-Fi (Free)
6
Annex King
Room details
1 Extra-Large Double Bed
Sleeps 2
240 ft²
Balcony or PatioAir ConditioningHeatingWi-Fi (Free)
4
Two Queens
Room details
2 Large Double Beds
Sleeps 4
240 ft²
Air ConditioningHeatingWi-Fi (Free)
Guest reviews of Winslow's Bungalows - Key West Historic Inns
8.8
Fabulous
Based on 1,455 verified reviews
Who stays here?
Business
1%
Couple
81%
Family
7%
Group
8%
Solo
1%
What guests think
AI-generated summary based on recent guest reviews
At Winslow's Bungalows - Key West Historic Inns, travelers praise the lush, resort‑like grounds, multiple small pools with a bar, and a walkable, quiet‑yet‑central location, while service is frequently described as warm, responsive, and accommodating.
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What guests think
At Winslow's Bungalows - Key West Historic Inns, travelers praise the lush, resort‑like grounds, multiple small pools with a bar, and a walkable, quiet‑yet‑central location, while service is frequently described as warm, responsive, and accommodating.
Guests highlight the generous continental breakfast with fresh items like juices and wellness shots, plus occasional live music. Room experiences vary: some are spacious and charming, while others feel small or dark, with noisy or uneven AC, musty odors, thin walls, or soft flooring. Pool seating and towels can run short, and street‑facing rooms may hear traffic; a few reviews note housekeeping inconsistencies and surprise parking fees. Expect a tropical, boutique stay with character and some quirks.
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AI-generated summary based on recent guest reviews
Facilities
Lush grounds with several small pools, a pool bar, shaded seating and occasional live music create a relaxed vibe; water refill stations and bike delivery assistance are noted. Downsides include limited loungers or towels and paid or limited on-site parking.
Related guest reviews
8
Leslie
29 Apr 2024
·
Stayed 5 nights
Nice quiet property, enjoyed our stay. Was able to walk to Duval Street and all the shops there. Only complaint was that seating and lounging options around the pools were limited. Most were snatched up early and saved all day. Would have been nice to have a closet and more space in the bathroom.
Nice quiet property, enjoyed our stay. Was able to walk to Duval Street and all the shops there. Only complaint was that seating and lounging options around the pools were limited. Most were snatched up early and saved all day. Would have been nice to have a closet and more space in the bathroom.
10
Kristina
17 Mar 2025
·
Stayed 3 nights
The property was clean with many amenities. The pools were great with plenty of chaise lounges. We were sorry there wasn’t a hot tub.
The property was clean with many amenities. The pools were great with plenty of chaise lounges. We were sorry there wasn’t a hot tub.
10
juliette C
8 Mar 2025
·
Stayed 5 nights
Nice to have your own little bungalow and outside seating area with privacy. The bar and two pools wee also very nice and convenient as well as the ability to rent bikes there as well. Great breakfasts! And bar !
Nice to have your own little bungalow and outside seating area with privacy. The bar and two pools wee also very nice and convenient as well as the ability to rent bikes there as well. Great breakfasts! And bar !
10
Mary
10 Apr 2025
·
Stayed 4 nights
The hotel was very nice except it needed more lounge chairs poolside.
The hotel was very nice except it needed more lounge chairs poolside.
10
Ruta K
3 Jan 2025
·
Stayed 4 nights
Property was fantastic-bungalos amazing for privacy and space. 3 piols, bar, morning breakfast! Staff super helpful from management, front desk, housekeeping and bar. So close to shops.
Property was fantastic-bungalos amazing for privacy and space. 3 piols, bar, morning breakfast! Staff super helpful from management, front desk, housekeeping and bar. So close to shops.
10
Renee
22 Aug 2025
·
Stayed 3 nights
Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.
Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.
10
Bradley
28 May 2025
·
Stayed 4 nights
Wow! This was a great place to stay in Key West. The grounds are gorgeous, and the rooms are quaint. It’s the perfect key west experience- the pools are also a nice touch- they aren’t huge, but there are 3!
Wow! This was a great place to stay in Key West. The grounds are gorgeous, and the rooms are quaint. It’s the perfect key west experience- the pools are also a nice touch- they aren’t huge, but there are 3!
10
Rebecca
28 Jul 2025
·
Stayed 2 nights
Lovely property!! Only Complaint is there are rarely available towels for the pool. They can’t seem to keep up. Other than that, we love this property!
Lovely property!! Only Complaint is there are rarely available towels for the pool. They can’t seem to keep up. Other than that, we love this property!
10
Adam
19 Jun 2025
·
Stayed 4 nights
Our stay here was magical! We arrived around midnight due to flight issues and were met by a friendly Manager to check us in. The grounds are gorgeous and there's little areas all over the property to tuck yourself away and read a book or enjoy a drink. We stayed in the Annex across the street. It was so cute and we had our own little pool all to ourselves the entire time. It's a very quick walk to the "main" pool by the bar and restaurant. The complimentary buffet for breakfast was wonderful and the drinks at the bar were delicious! I really appreciated the purified water stations for refilling our bottles. The location of the Winslow is hard to beat. Your right smack dab in the middle and can be anywhere on the island in 5 minutes to 15 minutes via bike. Definitely rent a bike, it's so much fun to cruise around!
Our stay here was magical! We arrived around midnight due to flight issues and were met by a friendly Manager to check us in. The grounds are gorgeous and there's little areas all over the property to tuck yourself away and read a book or enjoy a drink. We stayed in the Annex across the street. It was so cute and we had our own little pool all to ourselves the entire time. It's a very quick walk to the "main" pool by the bar and restaurant. The complimentary buffet for breakfast was wonderful and the drinks at the bar were delicious! I really appreciated the purified water stations for refilling our bottles. The location of the Winslow is hard to beat. Your right smack dab in the middle and can be anywhere on the island in 5 minutes to 15 minutes via bike. Definitely rent a bike, it's so much fun to cruise around!
8
Thomas C.
15 Mar 2025
·
Stayed 3 nights
Historical buildings but well maintained. Small swimming pools for lounging and cooling off. A/C in our bungalow had a loud motor.
Historical buildings but well maintained. Small swimming pools for lounging and cooling off. A/C in our bungalow had a loud motor.
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AI-generated summary based on recent guest reviews
Cleanliness
Most guests find rooms and grounds very clean, but several report musty or mildew odors, occasional mold, humidity issues, or missed housekeeping.
Related guest reviews
10
patrick
3 Oct 2025
·
Stayed 5 nights
Comfortable bed, very clean room and service. Breakfast was excellent
Comfortable bed, very clean room and service. Breakfast was excellent
6
Troy Alan
2 Feb 2025
·
Stayed 8 nights
Poor room cleanliness
Poor room cleanliness
10
Lynn
15 Jul 2024
·
Stayed 3 nights
Loved every minute here! Beautiful property, exceptionally clean and staff was wonderful. The breakfast is a lovely way to start the day. This was a great place to stay in a great location. Can’t wait to return!
Loved every minute here! Beautiful property, exceptionally clean and staff was wonderful. The breakfast is a lovely way to start the day. This was a great place to stay in a great location. Can’t wait to return!
6
phyllis
3 Oct 2024
·
Stayed 4 nights
The property location is great for walking to many restaurants and attractions. Building is beautiful but has some repairs needed. Room was ok but didn’t cooldown for comfortable sleeping at night. I was put in a room upstairs far away from the bar, ice, and breakfast. Room maid service had to be requested and then was not done well. Floors were filthy. The daily resort amenities fee of $35?! For what? Relaxing at the pool when the staff started power washing! Not worth the extra costs! There are many other choices close by. Very disappointed
The property location is great for walking to many restaurants and attractions. Building is beautiful but has some repairs needed. Room was ok but didn’t cooldown for comfortable sleeping at night. I was put in a room upstairs far away from the bar, ice, and breakfast. Room maid service had to be requested and then was not done well. Floors were filthy. The daily resort amenities fee of $35?! For what? Relaxing at the pool when the staff started power washing! Not worth the extra costs! There are many other choices close by. Very disappointed
8
Linda
13 Mar 2025
·
Stayed 5 nights
The gardens and pools were beautiful and well maintained. The property was very walkable to Duval St. The room itself had very little storage for our belongings and had a very strong mildew smell. I would suggest the property owners install dehumidifiers or whatever needs to be done to eliminate the mildew smell, as it really detracted from the experience, especially at the price point.
The gardens and pools were beautiful and well maintained. The property was very walkable to Duval St. The room itself had very little storage for our belongings and had a very strong mildew smell. I would suggest the property owners install dehumidifiers or whatever needs to be done to eliminate the mildew smell, as it really detracted from the experience, especially at the price point.
10
Rachel
25 Nov 2025
·
Stayed 3 nights
Room was extremely clean and spacious
Room was extremely clean and spacious
4
Flavia
21 Jul 2025
·
Stayed 1 night
The room was humid and smelled bad. They had the AC going on plus a fan and an extra AC when we checked in. The loud floor AC blew air directly onto the bed, and the wall thermostat didn't work. The bed linens felt wet. This was not a four-star room.
The room was humid and smelled bad. They had the AC going on plus a fan and an extra AC when we checked in. The loud floor AC blew air directly onto the bed, and the wall thermostat didn't work. The bed linens felt wet. This was not a four-star room.
4
dominick
19 Apr 2025
·
Stayed 6 nights
The housekeeping was terrible, our room was only cleaned once during our stay. We had to call for towels every day because the room wasn’t cleaned! Three pools are advertised but they are tiny, and one of them is across the street! The air conditioner sounded like a freight train! I would not recommend staying there!
The housekeeping was terrible, our room was only cleaned once during our stay. We had to call for towels every day because the room wasn’t cleaned! Three pools are advertised but they are tiny, and one of them is across the street! The air conditioner sounded like a freight train! I would not recommend staying there!
8
Francia
30 Aug 2024
·
Stayed 2 nights
Beautiful property and great customer service. The breakfast was good. Unfortunately there was a sewage smell at my bungalow coming from the bathroom and mold in the shower. I only stayed there 2 nights.
Beautiful property and great customer service. The breakfast was good. Unfortunately there was a sewage smell at my bungalow coming from the bathroom and mold in the shower. I only stayed there 2 nights.
10
Freddy
30 Jul 2025
·
Stayed 4 nights
This is one of the nicest hotels I have stayed in for a very long time. It was very clean, and the staff was very friendly. They loved my dog. I will definitely be staying here again in September. and considering that it has a lot of trees, there is not one mosquito on the property.
This is one of the nicest hotels I have stayed in for a very long time. It was very clean, and the staff was very friendly. They loved my dog. I will definitely be staying here again in September. and considering that it has a lot of trees, there is not one mosquito on the property.
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AI-generated summary based on recent guest reviews
Rooms
Rooms range from spacious, quiet bungalows to very small or dark units with limited storage; decor is charming but variable in these historic buildings. Recurring comments cite loud or ineffective AC, thin walls, musty air, and occasional soft flooring.
Related guest reviews
8
Brenda Jeanne
9 Jun 2025
·
Stayed 1 night
Property was in good location. Beautiful grounds. Good breakfast. Room was very small. No closet.
Property was in good location. Beautiful grounds. Good breakfast. Room was very small. No closet.
4
David
4 Feb 2025
·
Stayed 4 nights
It's a historic hotel so I expected the smaller rooms. But what I didn't expect was the secondary lock on the room door not to work. I didnt expect to have to jiggle the door in order for it to close properly. I didnt expect to see drops of white pain on the floor or the smokey/musty smell. It is clear the hotel has not undergone a hotel renovation in years. I can see why Kimpton left. There is much better value to be had at hotels closer to Duval.
It's a historic hotel so I expected the smaller rooms. But what I didn't expect was the secondary lock on the room door not to work. I didnt expect to have to jiggle the door in order for it to close properly. I didnt expect to see drops of white pain on the floor or the smokey/musty smell. It is clear the hotel has not undergone a hotel renovation in years. I can see why Kimpton left. There is much better value to be had at hotels closer to Duval.
8
Vimal
22 Feb 2025
·
Stayed 2 nights
Property was charming and lush, location was very walkable to local attractions, breakfast buffet was varied and beds were comfy. Our room was just big enough for the four of us to move around, though we had no window, sink was so tiny with no counter that we kept splashing water on the floor, and we had a tough time figuring out how to work the AC because it was mounted too high on the wall to read the settings. Pools were charming but hard to get chairs given how small the pool areas were.
Property was charming and lush, location was very walkable to local attractions, breakfast buffet was varied and beds were comfy. Our room was just big enough for the four of us to move around, though we had no window, sink was so tiny with no counter that we kept splashing water on the floor, and we had a tough time figuring out how to work the AC because it was mounted too high on the wall to read the settings. Pools were charming but hard to get chairs given how small the pool areas were.
6
Lenore
10 Apr 2025
·
Stayed 4 nights
The property was cute, grounds were very nice, it was clean and a nice breakfast. However the rooms were relatively small and it was a bit further from areas we frequented than ideal. Additionally, we had to switch rooms at 4am due to faulty smoke alarm battery that was an issue during the day before and not properly fixed. Our room also had hot water for only 3 minute showers and the AC sounded like a jet engine. We complained about these things (along with mold on shower tiles). None of those items were fixed. The second room we were transferred to was lovely, so maybe we were unlucky with room 22. They did apologize and remove our resort fees for our stay.
The property was cute, grounds were very nice, it was clean and a nice breakfast. However the rooms were relatively small and it was a bit further from areas we frequented than ideal. Additionally, we had to switch rooms at 4am due to faulty smoke alarm battery that was an issue during the day before and not properly fixed. Our room also had hot water for only 3 minute showers and the AC sounded like a jet engine. We complained about these things (along with mold on shower tiles). None of those items were fixed. The second room we were transferred to was lovely, so maybe we were unlucky with room 22. They did apologize and remove our resort fees for our stay.
10
Dorit
3 Jun 2025
·
Stayed 1 night
AC was too loud
AC was too loud
4
Margaret
1 Jan 2025
·
Stayed 5 nights
The room that we were given (Room 61) was extremely tiny, and had no natural light (no windows). It also did not have anywhere at all to hang clothes, no closet, or even hooks other than one in the bathroom that had two robes on it. The room air conditioner was set on high when we arrived which I soon realized was to hide the overall musty smell. As our 5 day vacation went on, it became more uncomfortable, as it is increasing hard to come back after a long day out to a dark, musty and tiny room. Definitely not the experience we thought we would have at Winslow's Bungalows. It looked so nice in the ads and the landscaping was very nice. But is it even legal to rent a room without windows? I think they should at least have it posted it in the ad for these rooms that they are tiny and windowless. Then people know what they are getting. We came home with our luggage filled with musty clothes, including the winter coats we wore from home, as well as the inside of our luggage. I would not recommend staying here unless you are assured that you will not be assigned this room or any other like this as there may be more than one! We loved Key West though and can't wait to return, but will stay elsewhere for sure. I am very disappointed and feel deceived by Winslow's Bungalows.
The room that we were given (Room 61) was extremely tiny, and had no natural light (no windows). It also did not have anywhere at all to hang clothes, no closet, or even hooks other than one in the bathroom that had two robes on it. The room air conditioner was set on high when we arrived which I soon realized was to hide the overall musty smell. As our 5 day vacation went on, it became more uncomfortable, as it is increasing hard to come back after a long day out to a dark, musty and tiny room. Definitely not the experience we thought we would have at Winslow's Bungalows. It looked so nice in the ads and the landscaping was very nice. But is it even legal to rent a room without windows? I think they should at least have it posted it in the ad for these rooms that they are tiny and windowless. Then people know what they are getting. We came home with our luggage filled with musty clothes, including the winter coats we wore from home, as well as the inside of our luggage. I would not recommend staying here unless you are assured that you will not be assigned this room or any other like this as there may be more than one! We loved Key West though and can't wait to return, but will stay elsewhere for sure. I am very disappointed and feel deceived by Winslow's Bungalows.
8
Kevin
24 Jun 2025
·
Stayed 4 nights
Property is turn of the century Florida, which we loved. Flooring had some weak spots in the bedroom. The room was updated. Loved the sitting areas outside the rooms and variety of swimming pool options on site.
Property is turn of the century Florida, which we loved. Flooring had some weak spots in the bedroom. The room was updated. Loved the sitting areas outside the rooms and variety of swimming pool options on site.
8
Garrett
8 Aug 2025
·
Stayed 4 nights
My wife and I stayed here for a getaway together and absolutely loved it. The staff were very friendly and welcoming. The property was absolutely beautiful, quiet, relaxing. We loved the vibes and atmosphere. The included breakfast was above average. Gut health shots, chia pudding, boiled and deviled eggs to start off your day with good protein and nutrition. It was conveniently located to walk to all of the downtown restaurants and sites. The one thing that was subpar was the room itself. These buildings are from the 1800’s so it’s understandable that not everything is going to be perfect but the floor was mushy in a few spots and caving in like the subfloor was rotten. The air conditioning was not very cold despite us cranking it all the way down. These things could have been just our room/bungalow so it’s not necessarily a thumbs down because everything else was wonderful. Honestly if we vacation in Key West again we will most likely stay at Winslow’s again!
My wife and I stayed here for a getaway together and absolutely loved it. The staff were very friendly and welcoming. The property was absolutely beautiful, quiet, relaxing. We loved the vibes and atmosphere. The included breakfast was above average. Gut health shots, chia pudding, boiled and deviled eggs to start off your day with good protein and nutrition. It was conveniently located to walk to all of the downtown restaurants and sites. The one thing that was subpar was the room itself. These buildings are from the 1800’s so it’s understandable that not everything is going to be perfect but the floor was mushy in a few spots and caving in like the subfloor was rotten. The air conditioning was not very cold despite us cranking it all the way down. These things could have been just our room/bungalow so it’s not necessarily a thumbs down because everything else was wonderful. Honestly if we vacation in Key West again we will most likely stay at Winslow’s again!
10
Chris
6 Sept 2025
·
Stayed 6 nights
Great room, spacious and private
Great room, spacious and private
10
Beverly
7 Aug 2025
·
Stayed 3 nights
We especially liked the delicious breakfast. The beds were clean and comfortable. The room could use better lighting, an iron and a microwave.
We especially liked the delicious breakfast. The beds were clean and comfortable. The room could use better lighting, an iron and a microwave.
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AI-generated summary based on recent guest reviews
Service
Service is widely praised as friendly, attentive, and accommodating, with staff proactively assisting with requests and room moves. A few guests mention slow or uneven housekeeping and rare front-desk issues.
Related guest reviews
10
Jennifer Todd
18 Aug 2025
·
Stayed 3 nights
The staff is amazing! They always go above and beyond getting fast results if you need an item, need a recommendation, etc. Keep coming back year and year!
The staff is amazing! They always go above and beyond getting fast results if you need an item, need a recommendation, etc. Keep coming back year and year!
10
Nicole
7 Aug 2025
·
Stayed 3 nights
Beautiful property, great location and the staff were all incredibly nice and genuinely wanted to ensure that you had a fantastic stay.
Beautiful property, great location and the staff were all incredibly nice and genuinely wanted to ensure that you had a fantastic stay.
2
Jennifer
1 Sept 2025
·
Stayed 3 nights
This was the worst lobby experience and treatment. I had planned to stay again next year same weekend and reserve 3 rooms for 4 nights. We will not stay here again. The front desk lobby was and their “visitor” was close to be reporting to police as her behavior was atrocious. I am so disappointment and we were very much looking forward to another stay.
This was the worst lobby experience and treatment. I had planned to stay again next year same weekend and reserve 3 rooms for 4 nights. We will not stay here again. The front desk lobby was and their “visitor” was close to be reporting to police as her behavior was atrocious. I am so disappointment and we were very much looking forward to another stay.
10
Maureen
27 Jun 2024
·
Stayed 4 nights
We thoroughly enjoyed our recent stay. The room was clean and quaint, the property was very pretty and well-kept, the free breakfast was awesome. They arranged for bikes to be delivered to the property which we used for transportation the whole stay. The pools were great. And the location was perfect. It wasn’t in the middle of the party but close enough to get there. Staff were kind and accommodating.
We thoroughly enjoyed our recent stay. The room was clean and quaint, the property was very pretty and well-kept, the free breakfast was awesome. They arranged for bikes to be delivered to the property which we used for transportation the whole stay. The pools were great. And the location was perfect. It wasn’t in the middle of the party but close enough to get there. Staff were kind and accommodating.
10
Chesla Ann
3 Aug 2025
·
Stayed 4 nights
Amazing in every way!!!!
Amazing in every way!!!!
2
Kyle
18 May 2025
·
Stayed 4 nights
Got downgraded even though I paid for a higher end room. The next day they said they were going to “upgrade me” to a room with a balcony at no additional charge. That’s the room I paid for, it wasn’t an “upgrade” it was simply the room that I paid for. They acted like they did a favor and that annoyed me. She told me I didn’t book a room with a balcony, I showed her the reservation and she said “well that must be an issue with hotels.com, because thats not what was booked. Okay, well that’s between the property and hotels.com, not me then. Extremely unprofessional. I am a Marriott business traveler with over 800 nights in hotels and I never complain. But let me tell you this was honestly the worst stay in my lifetime of traveling. House keeping came in and made the bed. Didn’t bother to remove the trash. The walls were super thin so I could hear my neighbors yelling behind me at 2am. I thought it would be a cute place, I was very wrong. Just stay somewhere else.
Got downgraded even though I paid for a higher end room. The next day they said they were going to “upgrade me” to a room with a balcony at no additional charge. That’s the room I paid for, it wasn’t an “upgrade” it was simply the room that I paid for. They acted like they did a favor and that annoyed me. She told me I didn’t book a room with a balcony, I showed her the reservation and she said “well that must be an issue with hotels.com, because thats not what was booked. Okay, well that’s between the property and hotels.com, not me then. Extremely unprofessional. I am a Marriott business traveler with over 800 nights in hotels and I never complain. But let me tell you this was honestly the worst stay in my lifetime of traveling. House keeping came in and made the bed. Didn’t bother to remove the trash. The walls were super thin so I could hear my neighbors yelling behind me at 2am. I thought it would be a cute place, I was very wrong. Just stay somewhere else.
10
William Kraus Joseph
27 Oct 2024
·
Stayed 3 nights
The front desk was amazing! Sonya really made the trip stress free
The front desk was amazing! Sonya really made the trip stress free
10
Alexa
1 Nov 2024
·
Stayed 5 nights
Property was well maintained. Our first night the people above us were really loud so we talked to the front desk and they asked if we’d like to be moved. They moved us the next day and made sure they checked on us throughout the stay. I would definitely give them a 10/10 and would stay again.
Property was well maintained. Our first night the people above us were really loud so we talked to the front desk and they asked if we’d like to be moved. They moved us the next day and made sure they checked on us throughout the stay. I would definitely give them a 10/10 and would stay again.
8
Scott A
10 Jun 2024
·
Stayed 6 nights
The bungalows and property are amazing and have very beautifully landscaped gardens. Great private bungalows nestled into a scenic tropical paradise. We also used the swimming pool every midday after touring numerous beaches, historic sites, and restaurants. It's perfectly located in the middle of Old Town where all the fun starts. You can Uber anywhere for around 10 dollars and they are only minutes away when requested. The only negative is the cleaning service was hit or miss, so request maid service every day. The staff is very helpful and quick to rectify any needs or issues.
The bungalows and property are amazing and have very beautifully landscaped gardens. Great private bungalows nestled into a scenic tropical paradise. We also used the swimming pool every midday after touring numerous beaches, historic sites, and restaurants. It's perfectly located in the middle of Old Town where all the fun starts. You can Uber anywhere for around 10 dollars and they are only minutes away when requested. The only negative is the cleaning service was hit or miss, so request maid service every day. The staff is very helpful and quick to rectify any needs or issues.
10
Anne B
12 Nov 2024
·
Stayed 3 nights
Teqila and Ursula at the front desk were AMAZING! They insured that our Key West experience exceeded all our expectations. The property is wonderful from the comfy bedding to the delicious breakfast! Highly recommend!!
Teqila and Ursula at the front desk were AMAZING! They insured that our Key West experience exceeded all our expectations. The property is wonderful from the comfy bedding to the delicious breakfast! Highly recommend!!
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AI-generated summary based on recent guest reviews
Location
Walkable Old Town setting near Duval Street, attractions and dining, with many noting a quiet feel despite the central spot. Some mention street-facing noise and that upper-floor rooms require stairs with no elevator.
Related guest reviews
10
barton
25 May 2025
·
Stayed 3 nights
Great property, very good location, walkable to Duvall St.
Great property, very good location, walkable to Duvall St.
10
Christianne
27 Nov 2025
·
Stayed 4 nights
I loved this hotel. It’s about a 8 to 10 minute walk to Duval Street in a great location. The staff are so nice and helpful and the pools, bar and breakfast are all terrific features.
I loved this hotel. It’s about a 8 to 10 minute walk to Duval Street in a great location. The staff are so nice and helpful and the pools, bar and breakfast are all terrific features.
10
Erin
29 Jan 2025
·
Stayed 2 nights
Very nice property. It is a long walk from Duvall street but do-able.
Very nice property. It is a long walk from Duvall street but do-able.
10
Gwen C.
12 May 2025
·
Stayed 7 nights
This is our 5th time to Key West and the Winslow Bungalow's were wonderful. The location is close to Duval Street but just enough off the side street so it's quiet. There was some traffic noise on Truman, but nothing to complain about. The layout was super cute with all the bungalows, paths, sitting areas, pools, etc. The breakfast was fine to us as we are not big eaters, but if you are looking for a big breakfast, then you may want something else. Our room was #11. It was clean, just the right size, had a cute outside patio in the back, which we loved. The only thing I would change is request a single bungalow or a 2nd floor room as our neighbors above us had very heavy feat at 3 am and were loud. But this happens and not a game changer. Overall, it was great and would definitely love to stay again at this property. Thanks for a wonderful week! :)
This is our 5th time to Key West and the Winslow Bungalow's were wonderful. The location is close to Duval Street but just enough off the side street so it's quiet. There was some traffic noise on Truman, but nothing to complain about. The layout was super cute with all the bungalows, paths, sitting areas, pools, etc. The breakfast was fine to us as we are not big eaters, but if you are looking for a big breakfast, then you may want something else. Our room was #11. It was clean, just the right size, had a cute outside patio in the back, which we loved. The only thing I would change is request a single bungalow or a 2nd floor room as our neighbors above us had very heavy feat at 3 am and were loud. But this happens and not a game changer. Overall, it was great and would definitely love to stay again at this property. Thanks for a wonderful week! :)
10
Theodore
14 Sept 2024
·
Stayed 4 nights
We stayed in a free standing bungalow. We loved the peace and privacy of it. The property is great, with little pathways and lots of tropical landscaping, two pools and an outside bar. It's also a couple blocks from the main drag on Duval St. Great spot.
We stayed in a free standing bungalow. We loved the peace and privacy of it. The property is great, with little pathways and lots of tropical landscaping, two pools and an outside bar. It's also a couple blocks from the main drag on Duval St. Great spot.
10
rebecca
2 Nov 2024
·
Stayed 6 nights
Loved the location…quiet but soooo close to everything!
Loved the location…quiet but soooo close to everything!
10
Alice
27 Apr 2025
·
Stayed 4 nights
Walking distance only 2 blocks to Duval St for shopping and restaurants.
Walking distance only 2 blocks to Duval St for shopping and restaurants.
8
Jessica
28 Oct 2024
·
Stayed 3 nights
Loved the property but if you can’t do stairs you need to tell them. We were on the third floor, which worked for us but definitely wouldn’t have for everyone in our party. Luckily they got rooms on the first floor. No elevators.
Loved the property but if you can’t do stairs you need to tell them. We were on the third floor, which worked for us but definitely wouldn’t have for everyone in our party. Luckily they got rooms on the first floor. No elevators.
8
Carole
17 May 2025
·
Stayed 2 nights
A lovely oasis to relax in away from the busy town, but close enough to walk everywhere.
A lovely oasis to relax in away from the busy town, but close enough to walk everywhere.
10
Maria
9 Apr 2024
·
Stayed 3 nights
Not one but two swimming pools. Very clean, quiet, and everyone was very friendly. Duval St. and all the action within a short walk distance. Fantastic experience!
Not one but two swimming pools. Very clean, quiet, and everyone was very friendly. Duval St. and all the action within a short walk distance. Fantastic experience!
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AI-generated summary based on recent guest reviews
Dining
Breakfast is a highlight with fresh, varied options such as juices, wellness shots, fruit and waffles, and the pool bar is popular, sometimes with live music. Some find breakfast seating limited or the spread carb-heavy, and note extra charges for omelets.
Related guest reviews
10
Camille
13 Aug 2025
·
Stayed 1 night
We loved our stay! The grounds are well kept and very tropical. We only had one day to stay, Winslow made it feel like a true vacation. Don’t miss the continental breakfast! Really nice choices and beautiful live music Sunday morning. You also get a complimentary drink from the bar upon arrival. Overall, I would definitely stay here again.
We loved our stay! The grounds are well kept and very tropical. We only had one day to stay, Winslow made it feel like a true vacation. Don’t miss the continental breakfast! Really nice choices and beautiful live music Sunday morning. You also get a complimentary drink from the bar upon arrival. Overall, I would definitely stay here again.
10
paul
8 Nov 2024
·
Stayed 7 nights
The breakfast is awesome different everyday. Wellness shots and fresh juices. Staff is amazing very friendly and always accommodating. I’ve been coming to key west quite a bit lately and this stay was the best. Hope to return asap. Property is really cool too
The breakfast is awesome different everyday. Wellness shots and fresh juices. Staff is amazing very friendly and always accommodating. I’ve been coming to key west quite a bit lately and this stay was the best. Hope to return asap. Property is really cool too
10
Shannon
22 Jul 2025
·
Stayed 2 nights
Absolutely amazing resort . Breakfast was included in the rate and it was perfect . Definitely will be coming back !
Absolutely amazing resort . Breakfast was included in the rate and it was perfect . Definitely will be coming back !
6
Navit
1 Aug 2024
·
Stayed 4 nights
Bungalows were kinda small but nice. The continental breakfast wasn’t great and there’s a $15 up charge for an omelet?! The worst part was the loud banging at all times of the day but even more at night. Apparently there are avocado trees and they fall and land on the roof and it makes a VERY loud noise. Also being called to the room for no reason at 6am was not cool. We barely slept thanks to the loud noises.
Bungalows were kinda small but nice. The continental breakfast wasn’t great and there’s a $15 up charge for an omelet?! The worst part was the loud banging at all times of the day but even more at night. Apparently there are avocado trees and they fall and land on the roof and it makes a VERY loud noise. Also being called to the room for no reason at 6am was not cool. We barely slept thanks to the loud noises.
10
Andrew
28 Jul 2024
·
Stayed 4 nights
This place is so amazing and completely exceeded my expectations! The staff were so friendly and very accommodating, the whole place is super cute and quaint, was not super busy or overwhelming, so tranquil. The included breakfast was so good and the options had slight alterations everyday so it never got boring! They also offered delicious fresh fruit and smoothies every morning including a wellness shot which was so awesome. The location is so perfect and is right next to Duval street. We rented bikes and got everywhere in 10 min or less including beaches, but we also walked all of Duval street and it wasn’t bad! The three pools were super nice, there’s tons of places on the property to sit and read and many areas are shaded. The bar was also great and the food we ordered was awesome! It was the best experience I have ever had at a hotel and I have been to big fancy resorts. If you are considering a larger resort or hotel in the Keys I seriously would recommend looking into this place for the location, caring staff and the incredible charm. We will be back and I recommend this place to everyone I talk to!
This place is so amazing and completely exceeded my expectations! The staff were so friendly and very accommodating, the whole place is super cute and quaint, was not super busy or overwhelming, so tranquil. The included breakfast was so good and the options had slight alterations everyday so it never got boring! They also offered delicious fresh fruit and smoothies every morning including a wellness shot which was so awesome. The location is so perfect and is right next to Duval street. We rented bikes and got everywhere in 10 min or less including beaches, but we also walked all of Duval street and it wasn’t bad! The three pools were super nice, there’s tons of places on the property to sit and read and many areas are shaded. The bar was also great and the food we ordered was awesome! It was the best experience I have ever had at a hotel and I have been to big fancy resorts. If you are considering a larger resort or hotel in the Keys I seriously would recommend looking into this place for the location, caring staff and the incredible charm. We will be back and I recommend this place to everyone I talk to!
10
Mark
26 May 2025
·
Stayed 2 nights
Charming. Great atmosphere and solid breakfast
Charming. Great atmosphere and solid breakfast
10
Frances
1 May 2025
·
Stayed 3 nights
We would definitely recommend this hotel. It was cozy and the grounds were beautiful. The bartender was fabulous and we could have had a drink ever night at the bar it was a nice place to relax and meet fellow travelers.
We would definitely recommend this hotel. It was cozy and the grounds were beautiful. The bartender was fabulous and we could have had a drink ever night at the bar it was a nice place to relax and meet fellow travelers.
10
Janet
21 Mar 2024
·
Stayed 3 nights
Upon arrival there had been a misunderstanding on size of room, but they accommodated us and were very nice and attentive to the situation. The grounds are lovely. Nice staff, bar area and food court. The pools were clean and well supplied with towels. The breakfast selection was well equipped and had nice options. There was also small selection of lunch foods offered at the bar, prices were very affordable and food was fresh. I would definitely visit again.
Upon arrival there had been a misunderstanding on size of room, but they accommodated us and were very nice and attentive to the situation. The grounds are lovely. Nice staff, bar area and food court. The pools were clean and well supplied with towels. The breakfast selection was well equipped and had nice options. There was also small selection of lunch foods offered at the bar, prices were very affordable and food was fresh. I would definitely visit again.
10
Joseph Dominic
25 Apr 2025
·
Stayed 4 nights
The property was beautiful and relaxing. The two pools were nice and clean. The breakfast was great.
The property was beautiful and relaxing. The two pools were nice and clean. The breakfast was great.
6
Melinda
26 Feb 2025
·
Stayed 4 nights
Rooms were extremely small with almost no storage. Very disappointing, especially as we like to unpack when on vacation. Outside of the rooms was nice, and the staff at breakfast were very friendly. Note that the breakfast is extremely carb heavy, including pre-sweetening the yogurt, overnight oats and hot oats. Grateful for the hard-boiled eggs and ham, but would have preferred to exchange a couple of the extensive carb options for more protein (e.g. plain yogurt)
Rooms were extremely small with almost no storage. Very disappointing, especially as we like to unpack when on vacation. Outside of the rooms was nice, and the staff at breakfast were very friendly. Note that the breakfast is extremely carb heavy, including pre-sweetening the yogurt, overnight oats and hot oats. Grateful for the hard-boiled eggs and ham, but would have preferred to exchange a couple of the extensive carb options for more protein (e.g. plain yogurt)
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AI-generated summary based on recent guest reviews
10
Justin
4 weeks ago
·
Stayed 3 nights
The onsite bar was great! Good location, walking distance to many great restaurants.
The onsite bar was great! Good location, walking distance to many great restaurants.
10
Kristina
24 Sept 2026
·
Stayed 2 nights
Loved this place cute and cozy
Loved this place cute and cozy
10
Michael
21 Sept 2026
·
Stayed 2 nights
The room was clean and decorated for the keys. Breakfast was amazing. Take advantage of that. The location is great for getting to so many hotspots.
The room was clean and decorated for the keys. Breakfast was amazing. Take advantage of that. The location is great for getting to so many hotspots.
10
Tina
21 Sept 2026
·
Stayed 4 nights
A great place to stay. Centrally located and a beautiful property.
A great place to stay. Centrally located and a beautiful property.
10
Beth
17 Sept 2026
·
Stayed 4 nights
We thoroughly enjoyed our time here! The grounds are beautiful. The staff was great. The rooms are very clean and housekeeping did a great job each day. I loved the robes that were provided! The buildings are old, yes. And the floor in our room was uneven. Not desirable but not a deal breaker. Bar and bar staff was great. Breakfast was great for a continental. Plenty of options and fresh cut fruit every day. We’d definitely return!
We thoroughly enjoyed our time here! The grounds are beautiful. The staff was great. The rooms are very clean and housekeeping did a great job each day. I loved the robes that were provided! The buildings are old, yes. And the floor in our room was uneven. Not desirable but not a deal breaker. Bar and bar staff was great. Breakfast was great for a continental. Plenty of options and fresh cut fruit every day. We’d definitely return!
Property policies
Check-in
Check-out
From 16:00 to 23:59
Before 11:00
FAQs about Winslow's Bungalows - Key West Historic Inns
Is parking available at the property?
Self parking is available on-site for a fee of USD 30 per day, which includes in/out privileges. Limited parking is provided.
What type of breakfast is offered?
A complimentary continental breakfast is served daily from 8:00 AM to 11:00 AM.
Does the property allow pets?
Pets are allowed at the property with a fee of USD 50 per pet, per night. Service animals are exempt from fees.
What are the check-in and check-out times?
Check-in is from 4:00 PM until 11:59 PM, and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request, subject to availability.
What accessibility features are available for guests with disabilities?
The property features limited wheelchair accessibility, including step-free entrances and accessible public areas. However, specific details about accessible rooms and facilities are not provided.
What is the location like in relation to key landmarks?
The property is centrally located in Key West, just a 5-minute walk from Duval Street and 10 minutes by foot from Florida Keys Beaches. It is 0.4 miles from the Ernest Hemingway Home and Museum and 0.6 miles from South Beach.
Does the property have a swimming pool?
Yes, the property features a seasonal outdoor swimming pool, which is accessible from 7:00 AM to 10:00 PM.
What are the policies for guests staying with children?
Children are allowed at the property. The minimum age for children to stay for free is not specified.
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Instant AI responses are based on hotel information
Prices for upcoming dates
November 2026
Su | Mo | Tu | We | Th | Fr | Sa |
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December 2026
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Cheaper
Pricier
Average nightly price across deals, with taxes & fees.
Prices in USD for 2 guests, updated daily.
- 2026-10-31: 335.45486253509523USD
- 2026-11-01: 190.5190187210083USD
- 2026-11-02: 203.62321640090943USD
- 2026-11-03: 208.21611193771363USD
- 2026-11-04: 211.71458856124877USD
- 2026-11-05: 499.65707276763914USD
- 2026-11-06: NO DATA
- 2026-11-07: 692.982050201416USD
- 2026-11-08: 334.312560017395USD
- 2026-11-09: 258.60502688293457USD
- 2026-11-10: 267.1627429695129USD
- 2026-11-11: 262.1299915817261USD
- 2026-11-12: 293.55233385314943USD
- 2026-11-13: NO DATA
- 2026-11-14: NO DATA
- 2026-11-15: 262.46973959732054USD
- 2026-11-16: 262.5078140693665USD
- 2026-11-17: 262.0112395591736USD
- 2026-11-18: 263.1423999961853USD
- 2026-11-19: 301.42739242858886USD
- 2026-11-20: NO DATA
- 2026-11-21: 874.8646234405518USD
- 2026-11-22: 264.8660217758179USD
- 2026-11-23: 268.6437852470398USD
- 2026-11-24: 274.2542159225464USD
- 2026-11-25: 305.92065862426756USD
- 2026-11-26: 464.4756112121582USD
- 2026-11-27: NO DATA
- 2026-11-28: 282.7013485671997USD
- 2026-11-29: 212.43949028015138USD
- 2026-11-30: 216.8353999824524USD
- 2026-12-01: 216.62790436325074USD
- 2026-12-02: 239.59926894683838USD
- 2026-12-03: 392.3834781921387USD
- 2026-12-04: NO DATA
- 2026-12-05: NO DATA
- 2026-12-06: 310.31436383514404USD
- 2026-12-07: 252.4811547744751USD
- 2026-12-08: 248.8338493461609USD
- 2026-12-09: 278.08921072540284USD
- 2026-12-10: 282.68164485702516USD
- 2026-12-11: NO DATA
- 2026-12-12: NO DATA
- 2026-12-13: 261.69871444931033USD
- 2026-12-14: 248.16588844451906USD
- 2026-12-15: 244.74438104095458USD
- 2026-12-16: 252.4811547744751USD
- 2026-12-17: 286.50830018844607USD
- 2026-12-18: NO DATA
- 2026-12-19: NO DATA
- 2026-12-20: 270.64800973358155USD
- 2026-12-21: 318.2004277786255USD
- 2026-12-22: 356.1554471496582USD
- 2026-12-23: 356.86440475616456USD
- 2026-12-24: 356.4122618560791USD
- 2026-12-25: 665.3231678405762USD
- 2026-12-26: 690.4008470794678USD
- 2026-12-27: 695.9415372161865USD
- 2026-12-28: 726.7212275146485USD
- 2026-12-29: 458.2611327972412USD
- 2026-12-30: NO DATA
- 2026-12-31: NO DATA
The front desk is open daily from 7:00 AM - 11:00 PM. The front desk is staffed during limited hours. For any questions, please contact the property using the information on the booking confirmation. Information provided by the property may be translated using automated translation tools.
Check-in must be done by someone who is at least 21 years old.
You'll be required to pay the following fully refundable deposit.
Deposit: USD 50 per accommodation, per night
- 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
- The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
- This property accepts credit cards; cash is not accepted
- Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and outdoor lighting
- 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
- Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
- This hotel requires written authorization in advance for any payment using a credit card whose name differs from the registered guest.
- Pool access available from 7:00 AM to 10:00 PM.
- This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
- Self parking fee: USD 30 per day (in/out privileges)
- Pet fee: USD 50 per pet, per night
- Service animals are exempt from fees
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
Tour desk
Housekeeping
Safe-deposit box
Activities
Swimming pool
Garden
Pool outdoor
Outdoor Furniture
Pool (Seasonal Outdoor)
Terrace
Parking
Parking
Parking (Limited)
Parking Onsite
Services
Tour desk
Housekeeping
Safe-deposit box
Luggage storage
Concierge Services
General
Non-smoking rooms
Picnic area/Tables
Wheelchair Accessible (Limited)
Internet
Free wi-fi