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Rooms and Guests2 Guests, 1 Room
Key details

Hotel Details

725 Truman Avenue, Key West, Florida, United States, 33040

Winslow'S Bungalows - Key West Historic Inns - A 4-star historic property with three pools, continental breakfast, and gardens in Old Town

Situated in the heart of Key West Historic District, this 4-star Key West hotel occupies historic grounds that include the 1854 Maloney House, listed on the National Historic Register. The property features three swimming pools surrounded by landscaped gardens, hammocks, and swings. All rooms come equipped with air conditioning, flat-screen TVs, private bathrooms with designer toiletries, and high-speed WiFi. Winslow'S Bungalows - Key West Historic Inns provides complimentary continental breakfast served each morning by the pool, along with a poolside bar and 24-hour front desk service. Superior and deluxe rooms offer additional space and mini-fridges. Located five blocks from Duval Street's restaurants and shops, the property sits 8 minutes' walk from The Ernest Hemingway Home and Museum. Smathers Beach and Fort Zachary Taylor State Park are accessible within an 8-minute drive.

Pros

Historic Maloney House features a white exterior and inviting wrap-around porch

Three distinct outdoor pools offer multiple swimming options

Property includes garden swings and hammocks for relaxation

Free continental breakfast served poolside daily

Cons

6 miles distance from Key West International Airport

Limited on-site parking available for $30 per night

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Select room type

Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, and exclusive 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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Getting around

Discover available transportation options for smooth travel around the city

City Centre
Key West 1.5 km
Airports
Key West International (EYW) 5.0 km

Facilities

Hotel has comfortable rooms, premium services, and a prime downtown location

General

  • Non-smoking rooms
  • Free 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
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Check-in
23Oct2025Select date
Check-out
24Oct2025Select date
Rooms and Guests2 Guests, 1 Room