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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

S
ScottusUS
Verified booking
couple
Standard Room
Stayed in May 21, 2026

"Exceptional"

10.0
Helpful?
S
ShanebdBD
Verified booking
couple
Standard Room
Stayed in May 21, 2026

"Excellent"

8.0
Helpful?
T
ThomasfrFR
Verified booking
extended_group
Standard Room
Stayed in May 21, 2026

"Exceptional"

9.0
Helpful?
N
N8811FGdenisehCHARLESTON, WEST VIRGINIA
Verified booking
Couples
Standard Room
Stayed in May 20, 2026

"Nice and Super Clean"

10.0

Very nice. Clean. Quaint. I would.stay there again.

Helpful?
J
JanagbGB
Verified booking
couple
Standard Room
Stayed in May 20, 2026

"Very Good"

7.0
Helpful?
M
michaelnC9153WV
Verified booking
Couples
Standard Room
Stayed in May 19, 2026

"Laid-back tropical getaway"

10.0

Great location and authentic island atmosphere. Friendly and very helpful staff, particularly at the poolside bar. A fantastic place to stay in Key West

Helpful?
S
srs3720
Verified booking
Couples
Standard Room
Stayed in May 19, 2026

"We love it. Repeat customers and are first choice when in Key West."

10.0

Love the layout, the staff and proximity to things we care about. We always book her if available!

Helpful?
S
SarahbeBE
Verified booking
couple
Standard Room
Stayed in May 19, 2026

"Very Pleasant stay"

9.0

Very pleasant stay and perfect location! Hyghienic, like in the pictures. Nice breakfast and welcoming.

In busy periods it’s possible your room won’t be ready yet at 4PM (2 other couples as well)

Helpful?
S
SandragbGB
Verified booking
couple
Standard Room
Stayed in May 19, 2026

"Lovely peaceful chilled central property"

10.0

Location feel staff cleanliness quaint

Nothing

Helpful?
K
KevinAll
Verified booking
Couples
Standard Room
Stayed in May 18, 2026

"Awful experience, even just for the 1 night!!!"

2.0

An absoluteky awful hotel. Checked in, stayed 1 night then checked out the following morning having to spend £900 on alternative accommodation in the Keys. Bugs all over the room, 4 hours sleep because of the road noise (single glazed windows in a room directly next to US1), no free sun loungers and no pool towels. When I enquired about pool towels I was simply told, there mustn’t be any left and I guess they will be in the dryer waiting to be sorted! Grounds full of dead leaves and patio furniture 2 rusty chairs and a table. Couldn’t wait to check out, simply terrible place!

Helpful?
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