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Rooms and Guests2 Guests, 1 Room
Key details

Hotel Details

725 Truman Avenue, Key West, Florida, United States, 33040
-
Close to South Beach
Great
8.5
9.1
/10
5.0
4.0
/5

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

“Winslow's Bungalows impressed me with its seamless blend of historic charm and resort-style amenities; the chef-curated breakfast and poolside bar contribute to a relaxing, social atmosphere. Its location allows for easy exploration of Key West's attractions, yet the grounds offer a tranquil escape with lush gardens and multiple pools. I particularly appreciate the pet-friendly options, making it a welcoming choice for all travelers.”
Hotel logo
Charlotte EvansHead of Editorial at Hotelsdowntown
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Select room type

Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, and exclusive deals.
Annex King Mobility
2 persons
295 sq. feet 
1 King-size bed
Air conditioning
King Suite Soaking Tub
2 persons
410 sq. feet 
1 King-size bed
Bathtub
Air conditioning
King Suite Sofa Bed
2 persons
360 sq. feet 
1 King-size bed
Air conditioning
Classic King
2 persons
155 sq. feet 
1 King-size bed
Air conditioning
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Facilities

Hotel has comfortable rooms, premium services, and a prime downtown location
Facilities: Great
8.7/10Review score

General

  • Non-smoking rooms
  • Wi-Fi
  • On-site car park
  • Handicap 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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Winslow'S Bungalows - Key West Historic Inns 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
1700 ft
Church
Saint Mary Star of the Sea
300 ft
938 Whitehead St
Key West Lighthouse and Keeper's Quarters Museum
1900 ft
Museum
Key West Firehouse Museum
1200 ft
South Street Corner of South and Whithead Streets
Statue Of Bishop Albert Kee
1800 ft
1100 Simonton St
Historic E. H. Gato Building
1000 ft
Museum
Tennessee Williams Key West Exhibit
1100 ft
Gallery
Wild Side Gallery
1400 ft
Gallery
Alan S Maltz Gallery
1700 ft
Gallery
Frangipani Gallery
1500 ft
Gallery
Island Arts Co-op
1600 ft
Gallery
Key West Pottery
1700 ft
Restaurants
Better Than Sex
800 ft
926 Simonton Street
Duffy's Steak & Lobster House
800 ft
1007 Simonton St
Seven Fish
1000 ft
921 Truman Ave
Meet Burger USA
1000 ft
517 Truman Ave
Camille's Restaurant
1700 ft
1202 Simonton St
Ocean Grill & Bar
1900 ft
1075 Duval St Duval Square
Origami Sushi Bar
1900 ft
1075 Duval St. Ste C3
Blackfin Bistro
1400 ft
918 Duval St
Sushi Song
1300 ft
925 Duval St
Point 5 Tapas & Wine Bar
1500 ft
915 Duval St
Explore Key West
Explore Key West
Top Attractions
Activities
Dining
Entertainment
Ernest Hemingway Home and Museum
8 minutes' walk
Hemingway's historic residence, showcasing his life and works. Unique tours available in a lush garden setting.
Duval Street
Duval Street
11 minutes' walk
Famous for its vibrant nightlife, shops, and dining options. An essential stop for an authentic Key West experience.
Key West Cemetery
Key West Cemetery
6 minutes' walk
A fascinating and historic site filled with unique graves and stories. Offers a glimpse into the island's past.
Southernmost Point
Southernmost Point
12 minutes' walk
Iconic buoy marking the southernmost point of the continental US. A must-visit for photos and beautiful sea views.
Snorkeling at Western Dry Rocks
7 minutes' drive
Thrilling snorkeling adventure with vibrant marine life. Book ahead with local operators for equipment rental.
Relaxation at C. B. Harvey Rest Beach Park
7 minutes' walk
Peaceful beach park ideal for sunbathing and picnics. Facilities available for a perfect day by the water.
Better Than Sex
Better Than Sex
3 minutes' walk
Dessert-themed restaurant with a romantic ambiance. Known for decadent treats like the signature chocolate cake.
Seven Fish
Seven Fish
4 minutes' walk
Casual eatery offering fresh seafood with a local twist. Reservations recommended for dinner service.
Green Parrot Bar
12 minutes' walk
Lively bar renowned for live music and a vibrant atmosphere. Offers a mix of local acts and weekly events.
The Red Barn Theatre
12 minutes' walk
Intimate theater featuring local productions and performances. Family-friendly shows available throughout the year.
Getting around
City Centre
Key West18 min  ·  5000 ft
Airports
Key West International Airport (EYW)8 min  ·  3.1 mi
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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

Reviews and Ratings

Feedback about Winslow'S Bungalows - Key West Historic Inns from previous guests about their experience.
Review score
Based on 1108 verified reviews
8.9/10
Great
90%
Recommend
Breakfast
8.3/10
Cleanliness
8.9/10
Comfort
9.0/10
Facilities
8.7/10
Free Wi-Fi
8.5/10
Location
9.4/10
Paid Wi-Fi
7.5/10
Staff
9.1/10
Value for money
7.9/10
Pros
Beautiful grounds
Great location
Friendly staff
Delicious breakfast
Intimate feel
Cons
Tiny room
Misleading photos
Non-soundproof rooms
Guest reviews
based on 256 reviews
4.5/5
based on 1239 reviews
8.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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FAQs
About Winslow'S Bungalows - Key West Historic Inns
What are the check-in and check-out times at Winslow'S Bungalows - Key West Historic Inns?
Check-in is at 16:00 and check-out is by 11:00.
How far is Winslow'S Bungalows - Key West Historic Inns from Key West International Airport?
The hotel is 5 km from Key West International Airport, approximately a 10-minute drive.
What room amenities can guests expect at Winslow'S Bungalows - Key West Historic Inns?
Rooms include a flat-screen cable TV, small refrigerator, air conditioning, and private bathrooms with designer toiletries.
Is breakfast included for guests at Winslow'S Bungalows - Key West Historic Inns?
Complimentary continental breakfast is included for all guests.
What are some popular nearby attractions to Winslow'S Bungalows - Key West Historic Inns?
Nearby attractions include the Southernmost Point (1 km) and the Ernest Hemingway Home and Museum (1 km).
Does Winslow'S Bungalows - Key West Historic Inns have a pool?
The hotel features three outdoor pools that are open all year round.
Is there parking available at Winslow'S Bungalows - Key West Historic Inns?
On-site private parking is available for a fee of 30 USD per day.
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 Sugar Apple Health Food Store (0.5 km).
What additional services does Winslow'S Bungalows - Key West Historic Inns provide?
The hotel offers concierge services, luggage storage, and complimentary Wi-Fi.
Does Winslow'S Bungalows - Key West Historic Inns offer leisure activities?
Guests can enjoy hammocks, swings, and landscaped gardens within the property.
Can guests access any fitness amenities at Winslow'S Bungalows - Key West Historic Inns?
Recreation options include swimming in one of the three pools and relaxing in the garden.
Is there a bar or lounge area at Winslow'S Bungalows - Key West Historic Inns?
The hotel features a bar/lounge area for guests to enjoy.

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08Mar2026Select date
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Rooms and Guests2 Guests, 1 Room