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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

D
Daniel AlbertoarAR
Verified booking
couple
Standard Room
Stayed in May 18, 2026

"Una mala relación precio con servicio"

4.0

La vegetación

La habitación muy incómoda y chica

Helpful?
L
LaRaeusUS
Verified booking
solo_traveller
Standard Room
Stayed in May 18, 2026

"Wonderful stay in a good location, close enough to walk to everything but far enough away to be a peaceful stay."

8.0

Very cute and lovely, had a lot of great options. The property is beautiful and the rooms although small are very cute and comfortable.

Although they have 3 pools, the pools are small and there’s very few chairs available. Also the breakfast is fine but just a continental breakfast. The offerings are good quality but just know it’s not a full breakfast.

Helpful?
K
KristencaCA
Verified booking
solo_traveller
Standard Room
Stayed in May 17, 2026

"Exceptional"

10.0
Helpful?
K
KenusUS
Verified booking
solo_traveller
Standard Room
Stayed in May 15, 2026

"Exceptional"

9.0

Great small cottage rooms very clean and nice beds. Continental breakfast with coffee and orange juice each morning. Pool areas are small but always nice and bar adjacent to one with great bar staff. About 2 block walk to Duval St.

No complaints

Helpful?
W
willrF4375QR
Verified booking
Couples
Standard Room
Stayed in May 14, 2026

"Solid 4 out of 5."

8.0

Good place. Beautiful property. Solid location. But gone down a peg or two over last couple years. Among them: Added a donation to my reservation that was hidden in fine print while booking. Kind of weird. Food, drinks, happy hour have been curtailed since a Kimpton property.

Helpful?
S
StephaniegbGB
Verified booking
couple
Standard Room
Stayed in May 14, 2026

"Exceptional"

9.0
Helpful?
D
daniel fraenkeluyUY
Verified booking
family_with_children
Standard Room
Stayed in May 14, 2026

"lindo lugar en cayo hueso"

8.0

la ubicacion y las habitaciones estaban muy bien

no tenian habitaciones con 2 camas separadas

Helpful?
U
U5897YZheathercNEW ALBANY, OHIO
Verified booking
Couples
Standard Room
Stayed in May 11, 2026

"good location but not worth the cost"

6.0

We stayed here for 5 nights starting April 30th, 2026. I had high expectations, given the high cost ($700/night). When we checked in we had requested rooms next to each other and were told they did not have any available. We booked months ago, so i do not really believe that they did not have them even close. We stayed in room 17, which was upstairs. The room itself was nice, but the bathroom smelled like cat urine every time you showered. The pools had very few towels. The grounds were not kept up too well, so many leaves and rips in the cushions on the porches. They had a continental breakfast daily, which was good. I did appreciate that. The staff at the front desk were very nice and helpful. Overall, I liked the location, but would try somewhere else.

Helpful?
C
CindyusUS
Verified booking
couple
Standard Room
Stayed in May 11, 2026

"Exceptional"

9.0

Staff were very kind

Helpful?
A
AnaisusUS
Verified booking
couple
Standard Room
Stayed in May 10, 2026

"Exceptional"

10.0

Very quaint and clean! Centrally located .

Helpful?