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8.6 / 10 Guest Rating

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue, Key West, us

Winslow's Bungalows - Key West Historic Inns - main view

About the Property

Luxurious Amenities:
Winslow's Bungalows offers 3 swimming pools for ultimate relaxation and enjoyment. Free WiFi access throughout the property ensures you stay connected during your stay.

Convenient Location:
Situated just 1 km from the Southernmost Point and 750 meters from Duval Street, Winslow's Bungalows provides easy access to Key West's popular attractions.

Tranquil Surroundings:
Enjoy the serene landscaped gardens and unwind on the sun terrace with lounge chairs. The inn also features hammocks, swings, and 3 outdoor pools for a peaceful retreat.

To experience the luxury and tranquility of Winslow's Bungalows, book your stay now!

Facilities & Amenities

Parking
Non-smoking rooms
Air conditioning
Swimming pool
Terrace
Pets allowed
Luggage storage
Safety deposit box
Tour desk
Facilities for disabled guests

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

Please note that the property is located in a building with no elevator.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

Available Rooms

Double Room - Photo 1
Double Room - Photo 2
Double Room - Photo 3
Double Room - Photo 4
1/4

Double Room

The spacious double room features air conditioning, a private entrance, a balcony with garden views as well as a private bathroom boasting a shower. The unit has 1 bed.

40 m2
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVAir conditioningHair dryerBathrobeRadio

Single Queen

Non-refundable
Breakfast Included
20% OFF$202.23

$161.78

Includes taxes & fees
Annex - Photo 1
Annex - Photo 2
Annex - Photo 3
Annex - Photo 4
1/4

Annex

Featuring free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room features air conditioning and a TV. The unit has 1 bed.

20 sqm
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVAir conditioningHair dryerBathrobeRadio

Annex

Non-refundable
Breakfast Included
20% OFF$261.25

$209

Includes taxes & fees
Annex Mobility  - Photo 1
Annex Mobility  - Photo 2
Annex Mobility  - Photo 3
Annex Mobility  - Photo 4
1/4

Annex Mobility

The spacious double room offers air conditioning, as well as a private bathroom featuring a hairdryer. The unit offers 1 bed.

27 sqm
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVAir conditioningHair dryerBathrobeRadio

Annex Mobility

Non-refundable
Breakfast Included
20% OFF$261.25

$209

Includes taxes & fees
Room, 1 King Bed (Elizabeth Annex) - Photo 1
Room, 1 King Bed (Elizabeth Annex) - Photo 2
Room, 1 King Bed (Elizabeth Annex) - Photo 3
Room, 1 King Bed (Elizabeth Annex) - Photo 4
1/4

Room, 1 King Bed (Elizabeth Annex)

1 King Bed240 sq feet Internet - Free WiFi Entertainment - 55-inch LED TV with cable channelsFood & Drink - Mini-fridgeSleep - Premium bedding and bed sheets Bathroom - Private bathroom, bathrobes, designer toiletries, and a hair dryerPractical - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on requestComfort - Climate-controlled air conditioning, daily housekeeping, and heatingAccessibility - Hardwood flooring in roomEco-friendly - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbsNon-SmokingRoom is accessed via exterior corridors

22 m2
Sleeps 2
Amenities
Safety deposit boxTVTelephoneHair dryerBathrobePrivate bathroom

Annex King Room

Non-refundable
Breakfast Included
20% OFF$401.18

$320.94

Includes taxes & fees

Guest Reviews

8.6
Excellent1978 verified reviews
AI Summary

Guests highly rate the great location and frequently praise the friendly staff.

Categories

Cleanliness8.1
Service9.5
Location9.6
Room Quality7.5
Amenities8.6
Value for Money8.0
Food and Beverage8.6
Overall Experience9.0

Select topics to read reviews

T
thailandtravel.ch GmbHchCH
Verified booking
couple
Standard Room
Stayed in May 26, 2026

"Top Lage und schöne Anlage, aber Zimmer veraltet und Preis-Leistung schwach."

5.0

Die Lage des Hotels ist ausgezeichnet. Obwohl es direkt an der Hauptstrasse liegt, ist es sehr ruhig und angenehm. Die Anlage selbst ist sehr charmant und versprüht echtes Key-West-Flair. Besonders gefallen hat uns auch, dass es mehrere Pools gibt, auch wenn diese teilweise eher klein sind. Ein kleiner Geheimtipp: Durch eine Seitenstrasse getrennt gehört ein weiterer Bereich ebenfalls zum Hotelkomplex. Dort befindet sich ein zusätzlicher Pool, der während unseres Aufenthalts fast immer leer war.

Das Hotel und insbesondere die Zimmer sind bereits etwas in die Jahre gekommen. Die Hotelbilder entsprechen nicht ganz der Realität. Unser Zimmer hatte beispielsweise einen deutlichen Riss im Boden. Zudem war der Boden sehr schmutzig. Auf den ersten Blick fiel dies zwar nicht auf, aber nachdem wir mit einem feuchten Tuch darüber gewischt hatten, war dieses komplett schwarz. Das Personal war in Ordnung – weder besonders freundlich noch negativ auffällig. Insgesamt empfanden wir das Preis-Leistungs-Verhältnis als ungenügend. Wobei dies unserer Meinung nach generell ein Thema in Key West ist.

Helpful?
T
TiffanyusUS
Verified booking
couple
Standard Room
Stayed in May 26, 2026

"Exceptional"

9.0
Helpful?
A
AnnusUS
Verified booking
couple
Standard Room
Stayed in May 25, 2026

"We absolutely loved this hotel, a very unique experience!"

10.0

This hotel was absolutely charming and had lots of space. It's located very close to all that one wants to see and do in Key West without being in the middle of it. Duval Street 3 block away and Mallory Square a quick 5 minute cab ride or 15 minute walk. The breakfast was tasty and had a lot of variety.

The water pressure in our room was a little low.

Helpful?
3
344lorimCUYAHOGA FALLS, OHIO
Verified booking
Couples
Standard Room
Stayed in May 23, 2026

"Somewhere between awful and wonderful"

6.0

I had a hard time deciding whether to book this hotel or not because the reviews were so far apart. As someone who travels a lot, I would say this hotel is somewhere on the low end of average. That said, I'm not sure there are any true luxury hotels or inns in Key West, so this probably is one of the nicer places to choose from. I stayed 3 nights at the Hampton Inn at the airport before coming to Winslow's Bungalows and those rooms were newer, cleaner, and larger and the breakfast was better. We booked this room with Delta Miles and I can honestly say this hotel is not even close to worth the $600+ a night people claim to pay (again I guess it's a supply and demand issues in Key West). The room was okay - large enough, musty smelling, the large armoire was in bad shape - every time you pulled a drawer out a pile of sawdust appeared on the floor because the drawers no longer slide in and out - it was also missing a door and beat up. The a/c did not work very well, and the room never got below about 75 degrees all week (we stayed 5 nights). The bathroom was okay - the tiles in the shower were a little rough/old/grimy looking. We enjoyed the cute (very small) balcony at night. The biggest issue I had was how gross the floor was in the room. I'm not sure if it is mopped in between guests because after 20 minutes on day one the bottom of my brand-new white socks were black. I did not complain, just wore my socks when in the room (wish I'd had slippers). The location is great, staff very nice, and pools are decent. Breakfast is true continental - nothing cooked (unless you include the hard-boiled eggs). Also - as another reviewer noted - replace the toaster already. Overall, this hotel has a ton of potential but needs some love and attention.

Helpful?
V
victoriasJ4396FC
Verified booking
Couples
Standard Room
Stayed in May 23, 2026

"Beware Bungalow 44"

6.0

Arrival and grounds-arrived early about 2pm. It appeared based on the luggage in the front office that rooms are not ready prior to 4pm. But to be fair that is when check in is stated to be. We were able to keep our luggage in the lobby and they also gave us two free drink tokens to use at the bar. They texted us when the room was ready at exactly 4:02pm. The property is very beautiful. Lush and well maintained. The bungalows look to be in historic buildings and are charming. There are 2 pools. Small in size. Not many loungers. There is an outdoor bar with ample seating and shaded. There is also a breakfast area right next to the bar that is enclosed and air conditioned that is open at all times. After breakfast you can get ice and cold water as well as some fruit 24/7. We found this out on our own, we didn’t really get a run down of the property from anyone. We were given instructions to our room which was Bungalow 44. It’s was in a building that appeared to be an old historic home which is part of the Key West appeal. We were on the second floor, there is no elevator. They did not offer any bell hop service which was fine and we were able to get our luggage up and down the two times with minimal issues. The room- again we stayed in Bungalow 44. It was on the second floor front of the building facing Truman Street. It was small. It was modern, fresh, and clean. The a/c was excellent, the ceiling fan was also a nice touch. Queen bed, very comfortable, one small side table that had a phone which took up basically the whole table. There was a dresser with a tv on it which also housed the mini fridge which kept our drinks very cold. The dresser had 2 drawers and there were 4 drawers under the bed. One drawer has a safe in it so 3 usable drawers. There was really limited space to “unpack”. Shelves or smarter furniture would have really improved our stay. There was also a chair in the room, it was basically unusable as this had to be used as a catch-all. There is no closet or anywhere to hang clothes. There is one hook in the bathroom, however we quickly learned it is under and a/c vent and dripped on the clothes from condensation. So pretty much useless. The bathroom was modern and seemed upscale with the beautiful tiles floor and shower. The bathroom provides little privacy, so if you aren’t quite comfortable with your partner hearing everything, definitely rethink this room, it had a stand up shower, good water pressure, full-size toiletries. Again limited space to spread out. There seemed to be under utilized space. Extra shelves/vanity space would have been nice. The room also had access to the second floor porch area. It was a shared space but spread out enough that you weren’t stepping on your neighbor. Room noise- being in the front of the building you hear a lot of road noise pretty much all day and night. It’s far enough from Duval that you don’t hear partying and music. Breakfast- free breakfast is offered from 8am-10am daily. This was a good assortment and a step above a continental breakfast. There was waffles, bagels, bread, assorted pastries, yogurt, fresh fruits, granola, hard boiled eggs, juices, coffee, tea. It was a pretty nice spread. You can also order hot breakfast ala carte for an extra charge. Staff- for the most part, the staff we encountered were friendly. The housekeeping staff will stop what they are doing to fulfill a need. Bartenders were friendly. The front desk in my opinion couldn’t care less about providing help or are at all worried about your comfort or the quality of your stay. The Ugly- housekeeping didn’t get to our Bungalow until 4:30pm-5pm daily. We are early birds who like to pack our day with activity and then head back to the hotel for a cool nap in the room before dinner. This means that our room went uncleaned. We were provided fresh towels when asked. On Wednesday morning(we were checking out Thursday) I went to the front desk to ask if our room could be refreshed. The woman was very nice and even asked what time we would like housekeeping to come. We were going to be at the beach all day so I told her 10am would be great but anytime before 3pm was fine. We got back to the room at about 4pm. Our room was still not cleaned. Mind you housekeeping didn’t touch it once in our 4 nights there. I trudged back to the front desk and let the woman know that the room was not cleaned as she had promised. She said she could send housekeeping right that moment. However, we were back from our day out and it was once again no longer a good time. I simply requesting 2 sets of towels for that day and one set for the next day since we were checking out explaining as much to the front desk. Housekeeping came with the towels about 20 minutes later. One set. I said I requested two sets and they said they were told only one. Housekeeping returned a few minutes later with the other set. While this may sound like petty complaining, I assure you, I don’t mind a small room, I don’t mind my room going unclean. But don’t promise me something that can’t be delivered. This place seems to lack a real feel for what travelers need. I can only speak for Bungalow 44. Maybe other Bungalows are bigger, better accommodating to a traveler, perhaps if you pay more you get better, earlier housekeeping service, these are all things I can’t prove. Could I have asked for a different room, of course. But my husband and I are not those people, we made the best of the size and the room did have its better qualities. If you are staying for 1 or 2 nights, this place would be a good choice. There are hundreds of places to stay in Key West. If this place is on your list, I’d reconsider.

Helpful?
J
jamesmA4037FN
Verified booking
Family
Standard Room
Stayed in May 22, 2026

"Great Place to Stay!!"

10.0

The Winslow staff was very helpful and friendly. We stayed in the Classic King. Room which was very clean and bed was comfortable. They have housekeeping everyday. There are 3 pools as well as a bar. Free breakfast was good. There is a menu you can order from with charge. It's very close to Duvall Street

Helpful?
K
KathleenusUS
Verified booking
solo_traveller
Standard Room
Stayed in May 22, 2026

"Exceptional"

10.0
Helpful?
W
WandausUS
Verified booking
couple
Standard Room
Stayed in May 22, 2026

"Rooms are not nice ."

2.0

The gardens were nice .

Run down broken furniture, no closets , noisy moldy smelling a/c units inside the room .

Helpful?
G
GonzaloclCL
Verified booking
couple
Standard Room
Stayed in May 21, 2026

"Bien"

8.0

Ubicación y jardines

Habitación muy pequeña y escalas muy altas para llegar a la habitación

Helpful?
G
GeraldineusUS
Verified booking
couple
Standard Room
Stayed in May 21, 2026

"Had a wonderful and relaxing trip!"

10.0

Great location!

Absolutely nothing

Helpful?