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08Jan2026Select date
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Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

725 Truman Avenue, Key West, Florida, United States, 33040
-
Near South Beach
Great
8.6
9.1
/10
5.0
4.1
/5

Location

Winslow's Bungalows is situated just steps from Duval Street, providing access to the best of Key West's attractions. This historically rich property occupies grounds that once housed Key West's first motel and some of its oldest homes. Guests can explore local shops, beaches, and entertainment venues within a short walking distance.

Accommodations

The hotel offers a variety of charming room options, including the Bungalow for an authentic Key West experience and the Maloney showcasing a soaking tub. Guests can choose from spacious suites with amenities designed to enhance comfort and relaxation. All rooms reflect the unique spirit of Key West and provide a private retreat.

Dining

Dining at Winslow's is highlighted by Chef Mike's Continental Breakfast served at Bungalows Bar, featuring organic hard-boiled eggs, house-made pastries, and wellness juice shots. Weekend offerings include live music paired with breakfast, enhancing the dining experience. The on-site Bungalow Bar offers a selection of specialty cocktails and poolside bites in a lush atmosphere.

Entertainment

Guests can enjoy live music performances and rum tasting events at Bungalow Bar, featuring local musicians. The property hosts fun activities throughout the week, including drag shows and themed events. Nearby attractions like the Alan S. Maltz Gallery and Aqua Bar add to the vibrant entertainment options.

Pools and Relaxation

Winslow's Bungalows features three outdoor pools, providing a resort-like atmosphere for relaxation and leisure. Guests can enjoy afternoon poolside refreshers such as frozen grapes and fresh mango delivered daily. This inviting environment encourages socializing and unwinding in a tropical setting.

Highlights

Location: steps from Duval Street

Accommodations: Bungalow and Maloney

Dining: Chef Mike's Continental Breakfast

Entertainment: rum tasting events

Pools: three outdoor pools

Must-do experiences

  • Catch the sunset at Mallory Square with live local performers.
  • Taste the conch fritters at El Meson de Pepe for a local delight.
  • Visit the Ernest Hemingway Home & Museum for literary history.
  • Explore the charming alleys of Old Town for hidden gems.
  • Stroll through the Key West Farmers Market on Wednesdays for local goods.
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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Annex Mobility
2 persons
27 m² 
1 King-size bed
Air conditioning
Maloney King
2 persons
38 m² 
1 King-size bed
Bathtub
Air conditioning
Truman King Patio
2 persons
33 m² 
1 King-size bed
Air conditioning
Winslow
2 persons
14 m² 
1 King-size bed
Air conditioning
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Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • Non-smoking rooms
  • Wi-Fi
  • Parking
  • Safe deposit box
  • Concierge desk
  • Pets allowed for a fee
  • Rooms/ Facilities for disabled
  • Wheelchair access
  • 24-hour security
  • Luggage storage
  • Smoke detectors
  • Fire extinguishers
  • Key access

Services

  • Pet amenities available
  • Housekeeping
  • Tours/Ticket assistance

Dining

  • Bar/ Lounge area
  • Picnic area/ Tables

Children

  • Cots

Facilities for people with disabilities

  • Toilet for disabled
  • Bathroom for disabled

Spa & Leisure

  • Outdoor heated swimming pool
  • Garden area

Room features

  • Air conditioning
  • Terrace
  • Garden furniture
  • Ironing facilities

Bathroom

  • Free toiletries
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Location

725 Truman Avenue, Key West, Florida, United States, 33040
Map view
725 Truman Avenue, Key West, Florida, United States, 33040
Nearby
Cemetery
Key West Cemetery
490 m
Church
Saint Mary Star of the Sea
80 m
938 Whitehead St
Key West Lighthouse and Keeper's Quarters Museum
550 m
Museum
Key West Firehouse Museum
340 m
South Street Corner of South and Whithead Streets
Statue Of Bishop Albert Kee
530 m
1100 Simonton St
Historic E. H. Gato Building
280 m
Museum
Tennessee Williams Key West Exhibit
330 m
Gallery
Wild Side Gallery
410 m
Gallery
Alan S Maltz Gallery
510 m
Gallery
Frangipani Gallery
450 m
Gallery
Island Arts Co-op
470 m
Gallery
Key West Pottery
490 m
Restaurants
Better Than Sex
230 m
926 Simonton Street
Duffy's Steak & Lobster House
220 m
1007 Simonton St
Seven Fish
290 m
921 Truman Ave
Meet Burger USA
300 m
517 Truman Ave
Camille's Restaurant
490 m
1202 Simonton St
Ocean Grill & Bar
550 m
1075 Duval St Duval Square
Origami Sushi Bar
560 m
1075 Duval St. Ste C3
Blackfin Bistro
420 m
918 Duval St
Sushi Song
370 m
925 Duval St
Point 5 Tapas & Wine Bar
450 m
915 Duval St
Explore Key West
Explore Key West
Top Attractions
Activities
Dining
Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
8 minutes' walk
Hemingway's former residence offers guided tours showcasing his life, with beautiful gardens and ancestral cats roaming.
Southernmost Point
Southernmost Point
12 minutes' walk
A famous landmark with a colorful buoy marking the southernmost tip of the continental U.S., ideal for photos and relaxation.
Key West Lighthouse and Keeper's Quarters Museum
Key West Lighthouse and Keeper's Quarters Museum
7 minutes' walk
This historic lighthouse provides a challenging climb for breathtaking views, alongside exhibits in the keeper's quarters.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
A tranquil sanctuary featuring hundreds of butterflies amidst lush flora, perfect for families and nature lovers.
Water Sports Adventures
20 minutes' drive
Thrilling options like jet skiing, snorkeling, and parasailing are available from local outfits near the beach for adventure seekers.
Relaxing Beach Yoga
10 minutes' walk
Yoga classes at C.B. Harvey Rest Beach Park offer peaceful sessions with ocean views, perfect for relaxation and rejuvenation.
Better Than Sex
Better Than Sex
3 minutes' walk
A dessert bar with a seductive atmosphere known for its decadent sweet treats and charming cocktails. Reservations recommended.
Seven Fish
Seven Fish
4 minutes' walk
A cozy seafood restaurant serving fresh, creative dishes with local ingredients. Suitable for both casual and special occasions.
Smokin' Tuna Saloon
14 minutes' walk
A lively bar with live music nightly, offering a fun atmosphere for enjoying local tunes, cocktails, and tasty bites.
Red Barn Theatre
5 minutes' drive
Showcasing live theater performances, this intimate venue features comedies and dramas, appealing to all ages of the audience.
Getting around
City Centre
Key West18 min  ·  1.5 km
Airports
Key West International Airport (EYW)8 min  ·  5.0 km
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Property information and rules
Check-in
from 16:00-23:59
Check-out
until 11 am
Guest Parking
Private parking is possible on site at USD 30 per day.
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
The hotel Winslow'S Bungalows - Key West Historic Inns serves a full breakfast for free. 
Children & extra beds
There are no extra beds provided in a room. 
Pets
Pets allowed on request at the price of USD 50 per night.
Number of rooms:
85
Former name
kimpton winslow's bungalows, an ihg hotel
FAQs
About Winslow'S Bungalows - Key West Historic Inns
What is the check-in and check-out policy at Winslow'S Bungalows - Key West Historic Inns?
Check-in is from 16:00, and check-out is by 11:00.
What are the nearby attractions from Winslow'S Bungalows - Key West Historic Inns?
Nearby attractions include the Southernmost Point (1 km), The Ernest Hemingway Home and Museum (1 km), and Key West Butterfly and Nature Conservatory (1 km).
Is parking available at Winslow'S Bungalows - Key West Historic Inns?
Yes, private parking is available on-site for 30 USD per day.
What amenities are available in the rooms at Winslow'S Bungalows - Key West Historic Inns?
Rooms include air conditioning, flat-screen cable TVs, small refrigerators, private bathrooms with hairdryers, and free toiletries.
Does Winslow'S Bungalows - Key West Historic Inns offer breakfast?
A complimentary continental breakfast is served each morning by the pool.
What leisure facilities are available at Winslow'S Bungalows - Key West Historic Inns?
The hotel features three outdoor swimming pools, hammocks, swings, and landscaped gardens.
What dining options are available near Winslow'S Bungalows - Key West Historic Inns?
Nearby restaurants include Better Than Sex (0.5 km), Seven Fish (0.5 km), and Camille's Restaurant (0.5 km).
What additional services does Winslow'S Bungalows - Key West Historic Inns provide?
The hotel offers luggage storage, 24-hour security, concierge services, and free Wi-Fi.
How far is Winslow'S Bungalows - Key West Historic Inns from Key West International Airport?
The hotel is approximately 5 km from Key West International Airport and is a 10-minute drive away.

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