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From669US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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 historic 4-star retreat with three pools, continental breakfast, and gardens in Old Town

Set in the heart of Key West Historic District, Winslow'S Bungalows - Key West Historic Inns occupies historic grounds featuring the 1854 Maloney House, listed on the National Historic Register. This Key West hotel maintains three outdoor swimming pools surrounded by landscaped gardens, hammocks, and swings. The property serves a daily continental breakfast by the pool from 8 AM to 10 AM. Guest rooms come equipped with air conditioning, flat-screen TVs, private bathrooms with designer toiletries, and high-speed WiFi. Superior and deluxe rooms feature mini-fridges and additional space. The Bungalow Bar operates daily from 11 AM until dusk, offering poolside drinks and lunch service. The Ernest Hemingway Home and Museum stands 8 minutes away on foot, while the Key West Butterfly and Nature Conservatory is a 10-minute walk. Smathers Beach and Fort Zachary Taylor State Park are accessible within an 8-minute drive.

Pros

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

The Elizabeth Annex offers 11 rooms with a private pool for group bookings

Daily poolside refreshments include items like frozen grapes and fresh mango

Live music events include acoustic performers, violinists, and open mic nights

Cons

Key West International Airport is 6 miles away

Limited on-site parking available at $30 per night

“This Key West property cultivates a lush, tropical atmosphere that feels both intimate and accessible. The bungalow-style accommodations offer a charming, historic counterpoint to the lively Duval Street scene, which is easily walkable. I especially appreciate the multiple pools and bar areas, which create a relaxing, social vibe.”
Hotel logo
Isabella MooreSenior Editorial Director at Petfriendlyhotels
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Select your room type

Cozy rooms, spacious suites, and family-friendly homes, all with flexible cancellation policies & special 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

Enjoy premium amenities for a relaxing stay with your pet

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

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
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
8 minutes' walk
A historic house museum showcasing Hemingway's life and work, with guided tours and beautiful gardens.
Duval Street
Duval Street
11 minutes' walk
Key West's vibrant main street, filled with shops, bars, and restaurants, perfect for local culture and nightlife.
Southernmost Point
Southernmost Point
12 minutes' walk
An iconic buoy marking the southernmost point in the continental U.S., popular for photo opportunities.
Key West Lighthouse and Keeper's Quarters Museum
Key West Lighthouse and Keeper's Quarters Museum
7 minutes' walk
A historic lighthouse with panoramic views of Key West, showcasing maritime history and the lives of past keepers.
Snorkeling Tours
5-minute drive
Adventure awaits with local snorkeling charters showcasing vibrant reefs and marine life. Reservations recommended.
Yoga on the Beach
11 minutes' walk
Relaxing oceanfront yoga sessions offered at local beaches-great way to unwind. Check seasonal schedules for classes.
Better Than Sex
Better Than Sex
3 minutes' walk
A creative dessert bar with a sultry ambiance, featuring decadent desserts and themed cocktails. Reservations recommended.
Seven Fish
Seven Fish
4 minutes' walk
A casual eatery serving fresh local seafood with a twist. Signature dishes include fish tacos and homemade sauces.
Duffy's Steak & Lobster House
Duffy's Steak & Lobster House
3 minutes' walk
A relaxed steakhouse offering premium cuts and fresh seafood. Known for its vibrant bar scene and upscale yet casual vibe.
Sloppy Joe's
10 minutes' walk
A lively bar renowned for live music, tropical cocktails, and a storied history dating back to the 1930s.
Key West Theater
5-minute drive
A venue hosting live performances, concerts, and events across diverse genres, suitable for all ages.
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
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 located 5 km from Key West International Airport.
What popular attractions are near 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).
Does Winslow'S Bungalows - Key West Historic Inns offer any swimming pools?
The hotel features three outdoor swimming pools that are open all year round.
What amenities are provided in the rooms at Winslow'S Bungalows - Key West Historic Inns?
Rooms include air conditioning, a flat-screen TV, a small refrigerator, and a private bathroom with hairdryers and free toiletries.
Is breakfast included at Winslow'S Bungalows - Key West Historic Inns?
A complimentary continental breakfast is served each morning by the pool.
Are there any dining options at Winslow'S Bungalows - Key West Historic Inns?
The hotel features a poolside bar and is within walking distance to dining options such as Better Than Sex (0.5 km), Bobby's Monkey Bar (0.5 km), and Camille's Restaurant (0.5 km).
Is parking available at Winslow'S Bungalows - Key West Historic Inns?
On-site parking is available for a surcharge of 30 USD per day.
What types of services does Winslow'S Bungalows - Key West Historic Inns offer?
The hotel provides concierge services, luggage storage, and complimentary Wi-Fi access.
Is Winslow'S Bungalows - Key West Historic Inns suitable for families?
The hotel is family-friendly, featuring spacious accommodations and amenities like cots.
What recreational activities are available near Winslow'S Bungalows - Key West Historic Inns?
Guests can enjoy water activities such as jet skiing, kayaking, and scuba diving nearby.
How far is Winslow'S Bungalows - Key West Historic Inns from Duval Street?
The hotel is located 800 meters from Duval Street.

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