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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 ยท 2 adults

Available Rooms

Winslow - Photo 1
Winslow - Photo 2
Winslow - Photo 3
Winslow - Photo 4
Winslow - Photo 5
1/5

Winslow

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

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

Winslow

Non-refundable
Breakfast Included
20% OFF$320.79

$256.63

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

Winslet

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.

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

Winslet

Non-refundable
Breakfast Included
20% OFF$351.16

$280.93

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

Winslow Mobility

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

Winslow Mobility

Non-refundable
Breakfast Included
20% OFF$326.86

$261.49

Includes taxes & fees
Key Lime - Photo 1
Key Lime - Photo 2
Key Lime - Photo 3
Key Lime - Photo 4
1/4

Key Lime

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

17 sqm
Sleeps 2
1 Queen bed (151-180 cm wide)
Amenities
ShowerTVAir conditioningHair dryerBathrobeRadio

Key Lime

Non-refundable
Breakfast Included
20% OFF$320.79

$256.63

Includes taxes & fees
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$186.73

$149.38

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$240.45

$192.36

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$240.45

$192.36

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

B
BricknerusUS
Verified booking
couple
Standard Room
Stayed in Jun 20, 2026

"Excellent"

8.0
Helpful?
M
MichalgbGB
Verified booking
solo_traveller
Standard Room
Stayed in Jun 19, 2026

"Exceptional"

9.0
Helpful?
G
GususUS
Verified booking
solo_traveller
Standard Room
Stayed in Jun 19, 2026

"Exceptional"

10.0

Great location and very pet friendly

Helpful?
M
MaxgbGB
Verified booking
couple
Standard Room
Stayed in Jun 18, 2026

"Excellent"

8.0
Helpful?
R
RalfnlNL
Verified booking
extended_group
Standard Room
Stayed in Jun 17, 2026

"Goede locatie, heel vriendelijk personeel, genoeg parkeerplaatsen, wel betaald"

9.0

Karakteristiek hotel, goede locatie

Trappen voor een kamer op de begane vloer, geen lift, geen mogelijkheid om binnen te ontbijten

Helpful?
M
MooreusUS
Verified booking
solo_traveller
Standard Room
Stayed in Jun 13, 2026

"Exceptional"

10.0
Helpful?
B
BlakeusUS
Verified booking
couple
Standard Room
Stayed in Jun 12, 2026

"Secluded and pretty but still walking distance to everything that matters."

10.0

Amazing little place that's well thought out so there is a bit of privacy. Great breakfast setup too.

I really have nothing to complain about. It was a great stay.

Helpful?
S
SenadatAT
Verified booking
solo_traveller
Standard Room
Stayed in Jun 10, 2026

"Excellent"

8.0
Helpful?
R
RonaldusUS
Verified booking
couple
Standard Room
Stayed in Jun 10, 2026

"Perfect vacation! Just what we needed."

10.0

Great location. Close to everything.

All was great!!

Helpful?
L
L657XLcraigf
Verified booking
Couples
Standard Room
Stayed in Jun 8, 2026

"Beautiful Property but missed the mark with service"

8.0

The property and grounds were beautiful and well maintained. We enjoyed the location of our unit being close to the bar and pool. The unit was clean and comfortable but could have had some additional storage for clothes (not a big deal) We were warmly greeted upon check in by Crystal who provided us with all of the information about the property along with contact information should we need anything. The property is centrally located to everything you want to do in Key West. I highly recommend parking across the street by the Church. FREE Parking. Also, bring or rent bicycles. It's 100% easier than driving. Be aware, even Golf Carts and Scooters have to pay to park. We never used our car. We walked, biked or took and Uber. The Bar has a happy hour from 4-6 and the pools were clean and enjoyable. You can get food until 2pm. Breakfast offered limited options. Juice, Fruit, Bagels, some pastries, yogurt etc.. overall pretty good. You can order Omelets and Egg sandwiches for additional charge. There are plenty of breakfast places nearby if you are looking for more options. As this was out 35th wedding anniversary, I ordered Champagne and strawberries for our arrival and was told the strawberries would be in the refrigerator, but unfortunately a warm bottle of champagne was on the chair by the bed with no glasses. We packed the bottle in the ice bucket for a few hours and had to call for glasses. The phone in the room was not working so I texted the number provided. A woman came shortly with 2 cocktail glasses and said there are no Champagne glasses. Day 2. We were out most of the day and arrived back around 5pm to find the room had not been serviced by housekeeping. I texted the number again to ask why we didn't have service? We were told that they are making their way around.. ? at 5pm? with less than 25% occupancy at the hotel? They brought up a set of towels and left. Day 3. We left the property around 12pm and returned about 4. Once again no housekeeping and had to ask again for service. We went to the pool for about an hour while they finally cleaned up the room. Overall we enjoyed our stay but was expecting better service from a luxury property. Couple of other things we noticed. For breakfast service on Thursday morning, it had rained overnight and some of the seating was wet. It didn't appear that anyone tried to dry off the tables and chairs which made seating limited. As people were finishing up their meal, some had left their dishes on the tables. We watched the bartender do nothing while on his phone and tables needing cleaned for new guests. It took some time but the kitchen staff cleaned the tables. I found it odd the bartender would not be more helpful in keeping the area clean. This did not affect our service, but just an observation.

Helpful?