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Winslow's Bungalows - Key West Historic Inns

Top rated by guests

3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers

Room (Truman) | Premium bedding, in-room safe, individually decorated

Designer toiletries, hair dryer, bathrobes, towels

Premium bedding, in-room safe, individually decorated

Room (Truman) | Premium bedding, in-room safe, individually decorated

9.0Outstanding

(1,046 Ratings)

"Bed and pillows - super confortable! Hotel, gardens, trees, pools, bars, five stars! Service and love like home!!"

juan

Don't miss out! Price and availability may change

9.0 / 10.0

Outstanding(1,046 Ratings)

Hotel in Key West, FL

4-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this hotel

Hotel with 3 outdoor swimming pools, 5-minute walk to Duval Street
Along with 3 outdoor pools, this smoke-free hotel has a bar/lounge and a poolside bar. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include self parking, coffee/tea in a common area, and a microwave in a common area.
Winslow's Bungalows - Key West Historic Inns offers 85 accommodations, which are accessible via exterior corridors and feature safes and bathrobes. Each accommodation is individually furnished and decorated. Beds feature premium bedding. 55-inch LED televisions come with cable channels. Bathrooms include designer toiletries, complimentary toiletries, and hair dryers.

This Key West hotel provides complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is offered daily and irons/ironing boards can be requested.

3 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Amenities at Winslow's Bungalows - Key West Historic Inns

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

TV

Garden

Free parking

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

Available Rooms

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Hotels.com properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Hotels.com provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Hotels.com

$$$$

Top rated by guests

9.0Outstanding

(1,046 Ratings)

"Bed and pillows - super confortable! Hotel, gardens, trees, pools, bars, five stars! Service and love like home!!"

juan

Don't miss out! Price and availability may change

$$$$

9.0 / 10.0

Outstanding(1,046 Ratings)

Hotel in Key West, FL

4-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

Available Rooms

About this hotel

Hotel with 3 outdoor swimming pools, 5-minute walk to Duval Street
Along with 3 outdoor pools, this smoke-free hotel has a bar/lounge and a poolside bar. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include self parking, coffee/tea in a common area, and a microwave in a common area.
Winslow's Bungalows - Key West Historic Inns offers 85 accommodations, which are accessible via exterior corridors and feature safes and bathrobes. Each accommodation is individually furnished and decorated. Beds feature premium bedding. 55-inch LED televisions come with cable channels. Bathrooms include designer toiletries, complimentary toiletries, and hair dryers.

This Key West hotel provides complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is offered daily and irons/ironing boards can be requested.

3 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Amenities

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

TV

Garden

Free parking

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Hotels.com properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Hotels.com provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Hotels.com

Ratings and reviews

9.0 / 10.0

Outstanding(1,046 Ratings)

5.0 / 10.0

Fresh breakfast, loved the live music, was perfect for my week-long trip with my daughter and 3 month old granddaughter. Such a Key West vibe♥️

3.0 / 10.0

Front desk staff was very nice. But the room had no air conditioning in the bathroom and the ac unit was old not central air. Bed not comfortable and pillows were not great. Disappointing.

4.0 / 10.0

Breakfast and location were great!

5.0 / 10.0

Great place to get away. Very nice staff and relaxed atmosphere.

5.0 / 10.0

Nice and cosy hotel, can recommend for everyone!

4.0 / 10.0

All in all a very nice room. We enjoyed our stay.

5.0 / 10.0

We stayed in an actual bungalow. There are only 3 true alone bungalows on the property.. The room was clean and functional.. The for has a couple of soft spots where we're pretty sure there's no sub floor. The however is we didn't fall through during our stay. The getting desk staff was amazing.. The location is ideal. Choose enough to Duval for the fun but far enough away due the quiet. The poolss were cozy and one had a bar. A great place to get away

5.0 / 10.0

Loved our stay in the Winslet house. We were on the top floor and had so much privacy, we never worried about anyone seeing us on the balcony in just our robes.

5.0 / 10.0

Great room and great location.

5.0 / 10.0

Second time we stay here. Is well maintained and the staff is very friendly. It is well located, closed to everything. As soon as I find a good new deal I will be back ❤️

5.0 / 10.0

Comfortable bed, very clean room and service. Breakfast was excellent

5.0 / 10.0

.

5.0 / 10.0

Great room, spacious and private

10.0 / 10.0

Bed and pillows - super confortable! Hotel, gardens, trees, pools, bars, five stars! Service and love like home!!

10.0 / 10.0

This property is meticulously maintained. Lush landscape, clean pools, great drinks and the breakfast was delicious.

10.0 / 10.0

The property was resort-like, with lush tropical gardens. Beautiful! The air conditioner stayed on all night and the mattress was very comfortable.

10.0 / 10.0

This is just what we needed. Rented bikes down the street and went everywhere. This place was a great place to call home for a bit

10.0 / 10.0

So cute and cozy. Perfect retreat. Relaxing pools. Live music by the bar.

10.0 / 10.0

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.

10.0 / 10.0

Such a magical place. The grounds are beautiful and it is walking distance to Duval street restaurants and bars.

10.0 / 10.0

For a VIP property, a room upgrade would be more appreciated. If an upgrade was not possible, then getting a comparable arrangement would have been nice.

5.0 / 10.0

Amazing, clean, beautifully decorated. Loved everything!

8.0 / 10.0

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!

10.0 / 10.0

We especially liked the delicious breakfast. The beds were clean and comfortable. The room could use better lighting, an iron and a microwave.

10.0 / 10.0

Beautiful property, great location and the staff were all incredibly nice and genuinely wanted to ensure that you had a fantastic stay.

10.0 / 10.0

Great stay with a group of friends. We all loved it!

10.0 / 10.0

Nice quiet place. The room was not the biggest room but comfortable. In a room this size there was no room to place your luggage and a luggage rack could be placed in the bathroom to assist your customers, as we are not spring chickens anymore. It was an easy walk to Duval Street and the food/bar was excellent.

8.0 / 10.0

It was a very nice hotel overall, I didn’t complain but I booked a room with the option of having my own private area and we didn’t receive that.

10.0 / 10.0

Amazing in every way!!!!

10.0 / 10.0

Lovely lush garden setting and convenient to walk to places of interest.

10.0 / 10.0

The ladies at the front desk were amazing! Breakfast was well beyond expectations.

10.0 / 10.0

2nd time there. Love it.

10.0 / 10.0

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.

10.0 / 10.0

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!

10.0 / 10.0

We laughed so hard when we woke up and heard a chicken singing! We was like no freakin way! and sure enough there was one sitting in a tree doing its thing 😂 good times! PICELESS Everyone/other guests were so friendly ❤️ Highly recommend it’s a chill vibe and perfect location 5 minutes to everything

10.0 / 10.0

From the moment we arrived, we were completely charmed by this hotel. The atmosphere felt cozy and inviting—like a perfect mix of historic charm and thoughtful modern touches. Every corner had character, from the beautiful decor in the lobby to the little details in the room that made it feel special. What really stood out, though, was the service. Every staff member we interacted with was warm, professional, and genuinely eager to make our stay perfect.

10.0 / 10.0

Staff was amazing so nice and accommodating. Beautiful bungalows. Clean and the grounds very well kept. Will definitely go back.

10.0 / 10.0

We loved our time at Winslow! The staff was super helpful, the room was clean, and the site itself was a piece of paradise. We will be back!

10.0 / 10.0

Winslows Bungalows offered a safe, clean, and wonderful place for us to vacay!

10.0 / 10.0

Breakfast

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