
Find Historic Hotels in Sugarloaf Key, FL
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check availability on Sugarloaf Key Historic Hotels
Our top choices for Sugarloaf Key historic hotels

Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with swimming pool and dockage, just minutes to Key West!Cudjoe Key
9.0 out of 10, Wonderful, (164 reviews)
The price is AED 735
AED 1,269 total
includes taxes & fees
15 Feb - 16 Feb

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key WestCudjoe Key
8.8 out of 10, Excellent, (150 reviews)
The price is AED 1,377
AED 2,677 total
includes taxes & fees
6 Feb - 7 Feb

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming poolCutthroat Harbor Estates
8.4 out of 10, Very Good, (121 reviews)
The price is AED 1,286
AED 2,552 total
includes taxes & fees
22 Feb - 23 Feb

Charming cottages, dockage, pool, just minutes to Key West
Charming cottages, dockage, pool, just minutes to Key WestCudjoe Key
8.6 out of 10, Excellent, (121 reviews)
The price is AED 918
AED 1,619 total
includes taxes & fees
15 Feb - 16 Feb

Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key WestCudjoe Key
9.2 out of 10, Wonderful, (162 reviews)
The price is AED 1,010
AED 1,744 total
includes taxes & fees
12 Feb - 13 Feb

8.2 out of 10, Very Good, (1,000 reviews)

9.0 out of 10, Wonderful, (1,000 reviews)
The price is AED 1,352
AED 1,669 total
includes taxes & fees
1 Mar - 2 Mar

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!Old Town Key West
9.6 out of 10, Exceptional, (148 reviews)
The price is AED 697
AED 1,389 total
includes taxes & fees
4 Feb - 5 Feb
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Sugarloaf Key Hotel Reviews

Hyatt Vacation Club at Beach House, Key West
10/10 Excellent
Explore a world of travel with Expedia
More Accommodation Types in Sugarloaf Key
Hotels near popular Summerland Key Attractions
- Hotels near Duval Street
- Hotels near Mallory Square
- Hotels near Smathers Beach
- Hotels near Southernmost Point
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near South Beach
- Hotels near Stock Island Yacht Club & Marina
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Clarence S. Higgs Memorial Beach Park
Sugarloaf Key Hotels by Star Rating
Explore more hotels
- Hyatt Vacation Club at Beach House, Key West
- Pier House Resort & Spa
- Havana Cabana at Key West
- Hyatt Vacation Club at Windward Pointe, Key West
- La Concha Key West, Autograph Collection
- NYAH Key West - Adults Only
- Casa Marina Key West, Curio Collection by Hilton
- Hilton Garden Inn Key West / The Keys Collection
- The Laureate Key West
- The Southernmost Inn - Adults Only
- Hyatt Centric Key West Resort and Spa






































