Winslow'S Bungalows - Key West Historic Inns Exterior photoWinslow'S Bungalows - Key West Historic Inns Exterior photoWinslow'S Bungalows - Key West Historic Inns Exterior photo

Winslow'S Bungalows - Key West Historic Inns

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Check rooms and rates
From$139 /night
Check-in
08Sept
Check-out
09Sept
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

3-pool bungalow retreat 1 block from Duval Street in Key West

Amenities & Dining

Winslow's Bungalows offers 3 outdoor swimming pools open all year round, with a poolside bar serving happy hour specials. Complimentary refreshments are delivered poolside daily, and the on-site bar features live entertainment and creative cocktails. A complimentary continental breakfast curated by Chef Mike is served each morning, and guests receive a welcome drink upon arrival.

Rooms & Grounds

Each bungalow-style room includes a small refrigerator, a flat-screen cable TV, and a private bathroom with hairdryer and free toiletries. The property has landscaped gardens with hammocks and swings, a sun terrace with lounge chairs, and brick paths through lush tropical foliage. Private patios and a rooftop deck provide outdoor relaxation spaces.

Location & Attractions

The inn is 750 meters from Duval Street with its restaurants and nightlife, and 1 km from the Southernmost Point. The Ernest Hemingway Home and Museum is an 8-minute walk away, and the Key West Butterfly and Nature Conservatory is a 10-minute walk. Smathers Beach and Fort Zachary Taylor State Park are an 8-minute drive from the property.

Services & Accessibility

Accessible rooms are available with lower bathroom sinks, raised toilets, and grab rails, and the property offers wheelchair access. Concierge service, luggage storage, and a tour desk assist with planning activities, and public transport tickets can be arranged. A security alarm, smoke alarms, and 24-hour security are in place for guest safety.

Pet-Friendly Policies

Winslow's Bungalows offers pet-friendly options for guests traveling with pets. Pet bowls are provided on-site. The property also has private parking available for a surcharge.

Highlights

Pools: 3 outdoor pools open all year

Breakfast: Complimentary continental breakfast by Chef Mike

Location: 750 m from Duval Street

Outdoor Spaces: Private patios, rooftop deck, hammocks & swings

Service: Welcome drink & daily refreshments poolside

Accessibility: Wheelchair-accessible rooms with grab rails

“The historic charm of this Key West property, with its bungalow-style accommodations, is undeniable. Three outdoor pools and gardens create a relaxing resort-like atmosphere, a true oasis near the buzz of Duval Street. Chef-driven breakfasts and poolside cocktails add a sophisticated touch for families and couples alike.”
Hotel logo
James DavidEditor-in-Chief at Dogfriendly-hotels

Select your room type

The hotel provides many room choices—family rooms, doubles, and pet-friendly suites—with breakfast, free cancellation, and special offers
  • Annex Mobility
    2 persons
    27 m²
    1 King-size bed
    Air conditioning
  • Winslow
    2 persons
    14 m²
    1 King-size bed
    Air conditioning
  • Key Lime
    2 persons
    17 m²
    1 King-size bed
    Air conditioning
Show all rooms

Rates & availability calendar

See current prices and availability for your chosen dates!
September 2026 - September 2027
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Choose dates to see prices
Check-in/ Check-out

Facilities

Hotels feature amenities designed to keep both you and your pet comfortable
Facilities: Great
8.4/10Review score

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
Show more

Location

725 Truman Avenue, Key West, 33040
Explore Key West
Local Experiences
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
8 minutes' walk
Home of Nobel Prize-winning author Ernest Hemingway, featuring beautiful gardens and guided tours showcasing his life.
Southernmost Point
Southernmost Point
12 minutes' walk
Iconic buoy marking the southernmost point in the continental U.S., perfect for memorable photos against the Atlantic backdrop.
Duval Street
Duval Street
11 minutes' walk
Famous street packed with shops, bars, and eateries, offering vibrant nightlife and local culture in a lively atmosphere.
Key West Lighthouse and Keeper's Quarters Museum
Key West Lighthouse and Keeper's Quarters Museum
7 minutes' walk
Historic lighthouse offering panoramic views of Key West after climbing 88 steps, with rich maritime history.
Water Sports
6 minutes' drive
Thrilling kayaking, snorkeling, and diving experiences available through local vendors. Rentals and tours easily accessible.
Yoga on the Beach
8 minutes' walk
Relaxing beach yoga sessions where guests can unwind while enjoying ocean views. Classes cater to all levels.
Better Than Sex
3 minutes' walk
Romantic dessert-only restaurant known for indulgent sweet creations and intimate ambiance. Reservations recommended.
Seven Fish
4 minutes' walk
Seafood bistro highlighting fresh catch of the day in a cozy setting, offering daily specials and vegetarian options.
Duffy's Steak & Lobster House
3 minutes' walk
Steak and seafood restaurant with a casual vibe, featuring hearty portions and a range of dining options for all palates.
Sloppy Joe's Bar
11 minutes' walk
Historic bar known for live music, vibrant atmosphere, and classic cocktails. Enjoy nightly entertainment that's family-friendly.
Key West Theater
5 minutes' drive
Venue featuring local performances, live bands, and comedy shows, offering entertainment suitable for all ages.
Local transport and travel tips
  • City Centre
    Key West 18 min  ·  1.5 km
  • Airports
    Key West International (EYW) 8 min  ·  5 km
Want access to early-bird pet-friendly hotel deals?
Access exclusive discounts today!
Check Rates
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 true.
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 1393 verified reviews
8.9 /10
Great
88 %
Recommend
Cleanliness
8.6/10
Comfort
8.7/10
Facilities
8.4/10
Free WiFi
7.9/10
Location
9.4/10
Staff
9.0/10
Value for money
7.6/10
Pros
Convenient location
Delicious breakfast
Peaceful atmosphere
Cons
Tiny room
Guest reviews
based on 256 reviews
4.5/5
based on 1250 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.
Open reviews
FAQs
About Winslow'S Bungalows - Key West Historic Inns
What is the distance from Winslow'S Bungalows - Key West Historic Inns to the Southernmost Point?
The Southernmost Point is 1 km away from the hotel.
What time can guests check in and out of Winslow'S Bungalows - Key West Historic Inns?
Check-in is at 16:00 and check-out is at 11:00.
Is parking available at Winslow'S Bungalows - Key West Historic Inns?
Private parking is available on-site for a fee of 30 USD per day.
What amenities are available in the rooms at Winslow'S Bungalows - Key West Historic Inns?
Rooms include a flat-screen cable TV, small refrigerator, air conditioning, and private bathrooms with hairdryers and free toiletries.
What dining options are nearby Winslow'S Bungalows - Key West Historic Inns?
Nearby restaurants include Better Than Sex (0.5 km), Seven Fish (0.5 km), and New York Pasta Garden (0.5 km).
What recreational facilities does Winslow'S Bungalows - Key West Historic Inns offer?
The hotel features three outdoor swimming pools and landscaped gardens with paths.
Is Wi-Fi available at Winslow'S Bungalows - Key West Historic Inns?
Complimentary Wi-Fi is available throughout the hotel.
How far is the Ernest Hemingway Home and Museum from Winslow'S Bungalows - Key West Historic Inns?
The Ernest Hemingway Home and Museum is an 8-minute walk from the hotel.
What breakfast options are available at Winslow'S Bungalows - Key West Historic Inns?
Continental breakfast is served daily at the hotel.

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