Winslow's Bungalows - Key West Historic Inns
Hotel with 3 outdoor swimming pools, 5-minute walk to Duval Street
VIP Access
Choose dates to view prices
Photo gallery for Winslow's Bungalows - Key West Historic Inns





Reviews
9.2 out of 10
Wonderful
Popular amenities
Explore the area

725 Truman Avenue, Key West, FL, 33040
- Place, Duval Street5 min walk
- Place, Ernest Hemingway Home and Museum8 min walk
- Place, Southernmost Point11 min walk
- Airport, Key West, FL (EYW-Key West Intl.)8 min drive
VIP Access
Curated for quality and service, VIP Access stays consistently receive our highest guest ratings.
Room options
View all photos for Room (Winslet)

Room (Winslet)
9.0 out of 10
Wonderful
(46 reviews)
View all photos for Room (Truman)

Room (Truman)
10.0 out of 10
Exceptional
(1 review)
View all photos for Room (Maloney)

Room (Maloney)
10.0 out of 10
Exceptional
(2 reviews)
View all photos for Room, Mobility Accessible (Winslow)

Room, Mobility Accessible (Winslow)
9.6 out of 10
Exceptional
(12 reviews)
View all photos for Room (Blue Parrot)

Room (Blue Parrot)
8.8 out of 10
Excellent
(10 reviews)
View all photos for Room (Winslow)

Room (Winslow)
9.0 out of 10
Wonderful
(39 reviews)
View all photos for Room (Key Lime)

Room (Key Lime)
8.0 out of 10
Very good
(3 reviews)
View all photos for Suite (Treehouse)

Suite (Treehouse)
10.0 out of 10
Exceptional
(2 reviews)
View all photos for Bungalow

Bungalow
9.6 out of 10
Exceptional
(5 reviews)
View all photos for Room (Annex)

Room (Annex)
9.6 out of 10
Exceptional
(9 reviews)
View all photos for Room, Mobility Accessible (Annex)

Room, Mobility Accessible (Annex)
You may also like
Ad

Blue Flamingo Resort Key West
New Town
- Pool
- Hot tub
- Pet friendly
- Free WiFi
8.0 out of 10, Very Good, 1,862 reviews
$346 nightly
The price is $389
Jan 19 - Jan 20
Total with taxes and fees
About the neighborhood
About this property
Winslow's Bungalows - Key West Historic Inns
Similar properties

Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
- Pool
- Breakfast included
- Pet friendly
- Free WiFi
9.0 out of 10, Wonderful, 861 reviews
$484 nightly
The price is $545
Feb 8 - Feb 9
Total with taxes and fees
Property amenities
Room amenities
Policies
Important information
Frequently asked questions
Winslow's Bungalows - Key West Historic Inns Reviews
Reviews
9.2
Wonderful
9.4/10
Cleanliness
9.4/10
Staff & service
9.2/10
Amenities
9.2/10
Property conditions & facilities
Reviews
Dec 26, 2025
Liked: Cleanliness
Stayed 3 nights in Dec 2025
10/10 Excellent
William
Dec 7, 2025
William
Stayed 6 nights in Nov 2025
10/10 Excellent
Diania
Oct 21, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Diania
Stayed 3 nights in Oct 2025
10/10 Excellent
Lacey
Traveled with partner
Oct 17, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lacey
Stayed 2 nights in Oct 2025
10/10 Excellent
William
Traveled with partner
Oct 17, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
William
Stayed 3 nights in Oct 2025
10/10 Excellent
Steven
Oct 17, 2025
Wonderful stay!
Steven
Stayed 4 nights in Oct 2025
10/10 Excellent
Blake Gavin
Traveled with partner
Oct 17, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Blake Gavin
Stayed 7 nights in Oct 2025
8/10 Good
john
Traveled with family
Oct 17, 2025
Liked: Cleanliness
john
Stayed 5 nights in Oct 2025
10/10 Excellent
Brooke
Traveled with partner
Oct 15, 2025
Liked: Amenities
Brooke
Stayed 6 nights in Oct 2025
10/10 Excellent
Brenda Marie Van
Traveled with partner
Oct 14, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Brenda Marie Van
Stayed 3 nights in Oct 2025
10/10 Excellent
JESSICA
Traveled with family
Oct 13, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
JESSICA
Stayed 3 nights in Sep 2025
10/10 Excellent
Daniel
Traveled with group
Oct 12, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Daniel
Stayed 2 nights in Sep 2025
10/10 Excellent
Ellen, fleming island
Traveled with partner, Traveled with pets
Oct 12, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Ellen
Stayed 2 nights in Oct 2025
10/10 Excellent
Michael
Oct 11, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Michael
Stayed 5 nights in Oct 2025
10/10 Excellent
Paul
Traveled with partner
Oct 10, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Paul
Stayed 4 nights in Oct 2025
10/10 Excellent
Chris
Traveled with family
Oct 10, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Chris
Stayed 4 nights in Oct 2025
10/10 Excellent
Kristan
Oct 10, 2025
Kristan
Stayed 4 nights in Aug 2025
10/10 Excellent
Kim Vernon
Traveled with partner
Oct 9, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Kim Vernon
Stayed 7 nights in Sep 2025
10/10 Excellent
Brandy
Oct 9, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Brandy
Stayed 4 nights in Oct 2025
10/10 Excellent
Holly
Traveled with partner
Oct 9, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities


Holly
Stayed 3 nights in Oct 2025
10/10 Excellent
Jessica
Traveled with partner
Oct 8, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Jessica
Stayed 3 nights in Oct 2025
10/10 Excellent
David
Traveled with partner
Oct 8, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
David
Stayed 2 nights in Oct 2025
8/10 Good
Peter
Traveled with partner
Oct 7, 2025
Liked: Cleanliness, amenities
Peter
Stayed 2 nights in Oct 2025
10/10 Excellent
Luke
Oct 7, 2025
Luke
Stayed 1 night in Oct 2025
10/10 Excellent
Jean
Oct 6, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Jean
Stayed 4 nights in Oct 2025
Orbitz's Latest Trends
Hotels
- Casa Marina Key West, Curio Collection by Hilton
- Margaritaville Hollywood Beach Resort
- Hyatt Place Boca Raton/Downtown
- Hilton Garden Inn Key West / The Keys Collection
- 3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Parrot Key Hotel & Villas
- Fontainebleau Miami Beach
- Royal Palm Studio with Hot Tub
- THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
- Hotel Maren Fort Lauderdale Beach, Curio Collection by Hilton
- Southernmost Beach Resort and Guesthouses
- Lighthouse Hotel - Key West Historic Inns
- The Godfrey Hotel & Cabanas Tampa
- 1 Hotel South Beach
- Opal Key Resort & Marina, Key West
- Grand Beach Hotel
- Hard Rock Hotel Daytona Beach
- The Reach Key West, Curio Collection by Hilton
- H2O Suites - Adults Only
- Courtyard by Marriott Key West Waterfront
- The Laureate Key West
- Fairfield by Marriott Inn & Suites Key West at The Keys Collection
- Havana Cabana at Key West
- Southernmost House
- Ibis Bay Beach Resort
- Loews Miami Beach Hotel – South Beach
- Rooftop Resort - Clothing Optional - Adult Only
- Hyatt Vacation Club at Sunset Harbor, Key West

















