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 – A Favorite for Families in Key West

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From$139 /night
Check-in
20Jul
Check-out
21Jul
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

725 Truman Avenue, Key West, 33040
-
Close to South Beach
Great
8.4
9.1
/10
5.0
4.0
/5

Historic Accommodations

Winslow's Bungalows offers 37 rooms across historic structures including the 1854 Maloney House. Rooms feature high-speed Wi-Fi, flat-screen TVs, air conditioning, security safes, and private bathrooms with hairdryers. Superior and deluxe rooms include mini-fridges and additional space. The Treehouse Suite provides a separate living area and balcony, while the Maloney room includes a soaking tub.

Dining and Refreshments

Chef Mike's continental breakfast is served daily from 8 AM to 10 AM at Bungalows Bar, featuring organic hard-boiled eggs, house-made pastries, and wellness juice shots. The Bungalow Bar operates weekdays 11 AM-7 PM and weekends 8 AM-7 PM, serving poolside bites, specialty cocktails, and bottomless mimosas from 8 AM-10 AM on weekends. Afternoon poolside refreshers include frozen grapes and fresh mango.

Recreation and Entertainment

The property features 3 outdoor swimming pools, hammocks, swings, and a sun terrace with lounge chairs. Live music includes open mic nights, acoustic performers, and violinists at the Bungalow Bar. Water adventures such as jet skiing, kayaking, and scuba diving are available nearby. The Elizabeth Annex offers a private pool and sun deck for group getaways.

Key West Location

Located in Key West Historic District, the hotel is an 8-minute walk from The Ernest Hemingway Home and Museum and 10 minutes from Key West Butterfly and Nature Conservatory. Duval Street restaurants and shopping are within five blocks. Smathers Beach and Fort Zachary Taylor State Park are an 8-minute drive away. Key West International Airport is 5 km from the property.

Hotel Services

Services include concierge assistance, complimentary continental breakfast, two welcome drinks at Bungalows Bar, and yoga mats. Limited on-site parking is available for $30 per night. Pets are welcome for $50 per night. The property offers free WiFi access, a 24-hour front desk, luggage storage, and complimentary wireless Internet throughout.

“Winslow's Bungalows cultivates a distinctive resort vibe within Key West's historic district. I especially appreciate how it captures Old Town charm, providing a relaxing counterpoint to nearby Duval Street's lively atmosphere. The multiple pools and secluded gardens create a tranquil experience that many larger hotels simply can't match.”
Hotel logo
Grace WhitmanContent & Editorial Director at Familyhotels

Choose from a variety of room types

Choose from a wide variety of rooms designed for families, including double rooms, family suites, and rooms with breakfast included
  • Annex Mobility
    2 persons
    27 sq. feet
    1 King-size bed
    Air conditioning
  • Maloney King
    2 persons
    38 sq. feet
    1 King-size bed
    Air conditioning
    Bathtub
  • Truman King Patio
    2 persons
    33 sq. feet
    1 King-size bed
    Air conditioning
Show all rooms

Availability and pricing for your selected dates

Book your family’s getaway in a snap with up-to-date availability and pricing!
July 2026 - July 2027
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Choose dates to see prices
Check-in/ Check-out

Facilities

Each family-friendly hotel provides top-notch amenities for an unforgettable stay with your loved ones
Facilities: Great
8.4/10Review 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
Show more

Location

725 Truman Avenue, Key West, 33040
Explore Key West
Local Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
8 minutes' walk
Hemingway's historic residence offering guided tours, lush gardens, and an insight into the author's life.
Duval Street
Duval Street
11 minutes' walk
Famed street known for its vibrant atmosphere, shops, restaurants, and nightlife; a must-see for any visitor.
Key West Lighthouse and Keeper's Quarters Museum
Key West Lighthouse and Keeper's Quarters Museum
7 minutes' walk
Historic lighthouse with stunning views and informative exhibits about the maritime history of Key West.
Southernmost Point
Southernmost Point
12 minutes' walk
Iconic buoy marking the southernmost point in the continental USA, perfect for memorable photos.
Snorkeling at Western Dry Rocks
7 minutes driving
Exciting snorkeling adventures suitable for all levels; rentals and guided tours available nearby.
Relaxation at C.B. Harvey Rest Beach Park
7 minutes' walk
A peaceful beach park with sandy shores, great for sunbathing or picnics; perfect for family fun.
Kayaking at Smathers Beach
5 minutes driving
Thrilling kayaking experiences amidst beautiful scenery; rental services available on-site for convenience.
Better Than Sex
3 minutes' walk
Romantic dessert restaurant featuring decadent treats and a cozy, intimate atmosphere; reservations recommended.
Seven Fish
4 minutes' walk
Local seafood eatery known for its fresh catch and relaxed ambiance; vegetarian options available.
Duffy's Steak & Lobster House
3 minutes' walk
Family-friendly steakhouse offering hearty meals in a casual setting; great for all appetites.
Green Parrot Bar
15 minutes' walk
An iconic bar with live music and a laid-back vibe; perfect for belting out tunes at jam sessions.
Key West Theater
5 minutes driving
Local venue hosting a variety of performances, from concerts to comedy, catering to all ages.
Tips on navigating the city
  • City Centre
    Key West 18 min  ·  5000 ft
  • Airports
    Key West International (EYW) 8 min  ·  3.1 mi
Get access to exclusive early booking discounts for your family’s upcoming getaway
Book now and enjoy exclusive rates on your family vacation!
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

Family-focused reviews and ratings

Read feedback from other families who have stayed to ensure you make the right choice.
Review score
Based on 1353 verified reviews
8.9 /10
Great
88 %
Recommend
Cleanliness
8.6/10
Comfort
8.6/10
Facilities
8.4/10
Free WiFi
7.7/10
Location
9.3/10
Staff
9.0/10
Value for money
7.6/10
Pros
Spacious rooms
Delicious breakfast
Friendly staff
Gorgeous foliage
Fantastic parking
Cons
Broken toilet seat
Limited pool towels
Guest reviews
based on 256 reviews
4.5/5
based on 1246 reviews
8.4/10
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 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 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.
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 amenities are featured in the rooms at Winslow'S Bungalows - Key West Historic Inns?
Rooms include air conditioning, a flat-screen cable TV, a small refrigerator, and private bathrooms with hairdryers and free toiletries.
Which popular attractions are close to Winslow'S Bungalows - Key West Historic Inns?
Nearby attractions include the Southernmost Point (1 km), The Ernest Hemingway Home and Museum (0.5 km), and Duval Street (0.5 km).
What dining options are available at Winslow'S Bungalows - Key West Historic Inns?
A complimentary continental breakfast is served each morning by the pool.
Are pets allowed at Winslow'S Bungalows - Key West Historic Inns?
Yes, pets are allowed with possible additional charges.
What recreational facilities are available at Winslow'S Bungalows - Key West Historic Inns?
The hotel features three outdoor swimming pools and landscaped gardens with hammocks and swings.
What language services does the staff at Winslow'S Bungalows - Key West Historic Inns offer?
The staff speaks English.
What are the nearby dining options around 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).
Does Winslow'S Bungalows - Key West Historic Inns offer any business services?
The hotel provides luggage storage and concierge services.
Are there any accessibility features at Winslow'S Bungalows - Key West Historic Inns?
The hotel provides wheelchair access and accessible rooms designed for comfort and safety.
What unique features does Winslow'S Bungalows - Key West Historic Inns have?
The hotel combines historic charm with modern amenities in a tropical retreat setting.

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