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Winslow's Bungalows - Key West Historic Inns

Property class: 4

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Photo gallery for Winslow's Bungalows - Key West Historic Inns

A two-story building with a covered entrance, palm trees, and a bench outside. - Winslow's Bungalows - Key West Historic Inns (Key West)
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights. - Winslow's Bungalows - Key West Historic Inns (Key West)
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.' - Winslow's Bungalows - Key West Historic Inns (Key West)
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery. - Winslow's Bungalows - Key West Historic Inns (Key West)
A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions. - Winslow's Bungalows - Key West Historic Inns (Key West)
A short walk from Duval Street and Southernmost Point, Winslow's Bungalows - Key West Historic Inns provides a poolside bar, a garden, and a bar. Guests can connect to free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Air conditioning

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Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for Premier King with Patio or Balcony

A wooden bench with cushions, a small table with glasses, and a white gate in a garden with various plants.

Premier King with Patio or Balcony

9.0 out of 10
Wonderful
(58 reviews)
  • 17 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for King Suite with Sofa Bed

A modern hotel room with a bed, sofa, and a desk with a lamp.

King Suite with Sofa Bed

9.4 out of 10
Exceptional
(3 reviews)
  • 46 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Twin Sofa Bed

View all photos for King Suite with Soaking Tub

A bedroom with a large bed, a wicker chair, a desk with a lamp, and a painting on the wall.

King Suite with Soaking Tub

10.0 out of 10
Exceptional
(2 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for King Mobility

A neatly made bed with a floral pillow, a wooden headboard, and two bedside lamps. There are two framed pictures on the wall above the bed.

King Mobility

9.6 out of 10
Exceptional
(13 reviews)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Two Queens

A hotel room with two beds, a wooden headboard, a bedside table with a lamp, a wicker chair, and a large window with shutters.

Two Queens

8.8 out of 10
Excellent
(10 reviews)
  • 22 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Classic King

A modern bedroom with a bed, bedside table, lamp, and a ceiling fan.

Classic King

9.0 out of 10
Wonderful
(52 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Single Queen

Room

Single Queen

8.8 out of 10
Excellent
(5 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Treehouse King Suite

A modern bedroom with a bed, a sofa, a ceiling fan, and a wall-mounted mirror.

Treehouse King Suite

10.0 out of 10
Exceptional
(2 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Bungalow King

A bedroom with a large bed, a wicker chair, a desk with a lamp, and a painting on the wall.

Bungalow King

8.4 out of 10
Very good
(6 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Annex King

Room

Annex King

9.4 out of 10
Exceptional
(15 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Annex King Mobility

A two-story white house with a balcony, surrounded by lush greenery and a white picket fence.

Annex King Mobility

10.0 out of 10
Exceptional
(3 reviews)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed

About the neighborhood

Located in Old Town Key West, a neighborhood in Key West, Winslow's Bungalows - Key West Historic Inns is in the entertainment district and near a boardwalk/promenade. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and skydiving nearby. Visit our Key West travel guide
Map
725 Truman Avenue, Key West, FL, 33040

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    5 min walk - 0.3 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    8 min walk - 0.4 miles
  • A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.
    South Beach
    9 min walk - 0.5 miles
  • A building with a sign reading "The Key West Butterfly & Nature Conservatory".
    Key West Butterfly and Nature Conservatory
    9 min walk - 0.5 miles
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    11 min walk - 0.6 miles

Getting around

  • Key West Intl. Airport (EYW)
    9 min drive

Restaurants

  • Circle K
    7 min walk
  • 801 Bourbon Bar
    9 min walk
  • Old Town Tavern
    7 min walk
  • El Siboney Restaurant
    6 min walk
  • Better Than Sex
    4 min walk

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Self parking on site (USD 30 per day; includes in/out privileges)

Food and drink

  • Daily continental breakfast available 8:00 AM to 10:00 AM for a fee
  • A bar/lounge
  • A poolside bar
  • Coffee and tea in common areas

Restaurants on site

  • Bungalow Bar

Things to do

  • 3 outdoor pools

Family friendly

  • 3 outdoor pools
  • In-room crib
  • Mini-fridge

Conveniences

  • Limited-hour front desk
  • Luggage storage
  • Shared microwave
  • Water dispenser

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Tour and ticket assistance

Outdoors

  • Garden
  • Outdoor furniture
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Front entrance ramp
  • Hardwood flooring in room
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible pool
  • Wheelchair-accessible registration desk (30 inches high)

More

  • 15 buildings
  • 2 floors
  • Built in 1857
  • Comprehensive food waste policy
  • Locally-owned and organized tours and activities
  • Smoking not allowed
  • Some LED lighting used
  • Vegan dining options
  • Vegetarian dining options
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Free crib
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Toothbrush and toothpaste (on request)
  • Towels provided

Entertainment

  • 55-inch LED TV with cable channels

Food and drink

  • Mini-fridge

More

  • Access via exterior corridors
  • Air conditioning (climate-controlled)
  • Ceiling fan
  • Free local calls
  • Heating
  • Individually decorated
  • Individually furnished
  • Iron/ironing board on request
  • Phone
  • Recycling
  • Safe
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: anytime
Minimum check-in age: 21

Check-out

Check-out before 11 AM

Special check-in instructions

The front desk is open daily from 7:00 AM - 11:00 PM
Front desk staffed during limited hours
For any questions, please contact the property using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

Pets allowed for an extra charge of USD 50 per pet, per night
Service animals are welcome, and are exempt from fees
Food and water bowls are available

Children and extra beds

Children are welcome
Free cribs are available on request at the property

Property payment types

  • American Express
  • Diners Club
  • Discover
  • Mastercard
  • Visa

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 50 per accommodation, per night
  • Resort fee: USD 50.63 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Concierge service
  • In-room safe
  • Phone calls
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 30 per day (in/out privileges)
  • Pet fee: USD 50 per pet, per night
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
This property accepts credit cards; cash is not accepted
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and outdoor lighting
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
This hotel requires written authorization in advance for any payment using a credit card whose name differs from the registered guest.

We should mention

This property does not have elevators
Pool access available from 7:00 AM to 10:00 PM
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

Frequently asked questions

Does Winslow's Bungalows - Key West Historic Inns have a pool?

Yes, this property has 3 outdoor pools. Pool access is from 7:00 AM–10:00 PM.

Is Winslow's Bungalows - Key West Historic Inns pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 50 per pet, per night. Service animals are exempt from fees.

How much is parking?

Self parking is available for USD 30 per day.

What time is check-in at Winslow's Bungalows - Key West Historic Inns?

Check-in start time: 4:00 PM; Check-in end time: anytime.

What time is check-out at Winslow's Bungalows - Key West Historic Inns?

Check-out is at 11 AM.

Where is Winslow's Bungalows - Key West Historic Inns located?

Located in Old Town Key West, this hotel is within a 5-minute walk of Saint Mary Star of the Sea and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Winslow's Bungalows - Key West Historic Inns Reviews

9.2

Wonderful

9.4

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1077 out of 1462 reviews
Rating 8 - Good. 242 out of 1462 reviews
Rating 6 - Okay. 94 out of 1462 reviews
Rating 4 - Poor. 31 out of 1462 reviews
Rating 2 - Terrible. 18 out of 1462 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very cute and clean place to stay
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was excellent in their recommendations for dinners and bars.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Super cute and comfortable stay!
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice rooms, nice pools, good breakfast
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is perfect. Clean,cute and great location. We will definitely be back!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful resort with amazing staff!
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
The property is on a perfect location near enough from Duval action, but at the same time far enough to enjoy a quiet time when necessary. Excellent parking lot onsite if you’re driving! The very friendly and helpful staff, made our staying even better!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent hotel Friendly helpful staff Great location
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was great
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great Location. Friendly Staff
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
The staff was fantastic and we loved the hotel!!! Great location!
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property offered striking beauty and an ideal location. The staff we spoke with throughout our stay were consistently friendly and welcoming. I appreciated the amenities. The complimentary continental breakfast and two welcome drinks were excellent. I would gladly return for another visit.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay. Scooter rental store down the street (Minty's) was great. Happy hour and live music was nice to have by the pool. Rooms were really clean and house keeping staff was extremely friendly.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was well maintained and clean. The tropical plants and trees were beautiful and made it feel like a little oasis. Our room was clean and we had what we needed. The staff we interacted with were very friendly and welcoming. Breakfast was good and was just enough to get the day started. We enjoyed the bar and the pools and the welcome drink was a nice treat! Overall we had a great experience and we would recommend this place for the amenities and the location.
Stayed 4 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a great property! Not expensive but with all the amenities. Close to Duvall. The only drawback were the roosters! But I think that’s everywhere in Key West.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
👍 great place and bed is super comfy
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Lovely place and helpful staff. Rooms are very private feeling.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property. Walking distance to Duval. Friendly helpful staff. Highly recommend!!
Stayed 3 nights in Sep 2026
Verified review

8/10 Good

Liked: Staff & service, amenities
The exterior of the property is very beautiful, staff were all so kind and friendly, and the breakfast was a great perk every morning. Large property with 3 different parking lots and bike rentals. Very pet friendly resort, which was great since we were traveling with our senior dog.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I felt we got the feel of Key West by staying here. Located about two blocks off Duval Street, but so many trees and plants around the property, it seems so private. We stayed in a bungalow with our own private patio. There were 3 pools, free continental breakfast and the cutest bar area that we loved to hang out at. The bartenders were so personable and helpful with giving ideas of things to see and do in the Keys. I was extremely glad we chose to stay here! Was located within a mile or less of everything we wanted to do so we were able to walk everywhere. I miss it already!
Stayed 5 nights in Sep 2026
Verified review

6/10 Okay

Liked: Staff & service, amenities
Disliked: Property conditions & facilities
Centrally located, quiet very tranquil establishment. The only issue I had was the moldy air conditioner. When the technician opened it up, after complaining about the smell, it was full of black mold...not sure when was the last time, the "regular" maintenance was done... probably more than a decade ago.
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very private and personal. Breakfast and Bar was very nice and relaxing.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I would stay here and recommend people to stay here again. The grounds are tucked into the property with trees, hammock chairs. The breakfast is exceptional for a free daily breakfast bartenders are friendly. The pools are relaxing. Everything‘s well kept. There’s not a lot of noise or overly restrictive rules. It’s a refreshing place to be and only a few walkable blocks to Duval
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this place! Beautiful hotel and great location.
Stayed 2 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small room but clean and functional. Grounds are beautiful and well maintained. Only complaint was the chemicals in the pool bleached two of my swimsuits- so beware of that.
Stayed 7 nights in Aug 2026