Find Historic Hotels in Sugarloaf Key, FL

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Check availability on Sugarloaf Key Historic Hotels

Our top choices for Sugarloaf Key historic hotels

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (157 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is AED 1,194
AED 2,445 total
includes taxes & fees
2 Jun - 3 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1,019 reviews)
"Very clean room. Great location!"
United States
Gary
The price is AED 505
AED 755 total
includes taxes & fees
20 May - 21 May
Pegasus International Hotel

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Old Town Key West
9.8 out of 10, Exceptional, (156 reviews)
"Great location beautuful house!"
United States
Suzanne U.
The price is AED 350
AED 950 total
includes taxes & fees
20 May - 21 May
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.2 out of 10, Very Good, (1,002 reviews)
"This is our favorite place to stay! Great location and perfect accommodations for a trip to Key West!"
United States
Patti
The price is AED 884
AED 994 total
includes taxes & fees
19 May - 20 May
Amsterdam's Curry Mansion Inn

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (250 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is AED 559
AED 1,292 total
includes taxes & fees
19 May - 20 May
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Old Town Key West
9.8 out of 10, Exceptional, (44 reviews)
"Great location, one block from Duval Street but still quiet, clean and comfortable. "
United States
Jackie H.
The price is AED 586
AED 1,541 total
includes taxes & fees
30 May - 31 May
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (120 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is AED 722
AED 1,474 total
includes taxes & fees
8 Jun - 9 Jun
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Old Town Key West
9.6 out of 10, Exceptional, (157 reviews)
"Great location and accommodations. "
United States
Brenda W.
The price is AED 435
AED 1,057 total
includes taxes & fees
24 May - 25 May
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Old Town Key West
9.8 out of 10, Exceptional, (149 reviews)
"The host was awesome, we really enjoyed our stay "
United States
Asgeir S.
The price is AED 350
AED 950 total
includes taxes & fees
19 May - 20 May
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!

FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!
Old Town Key West
9.4 out of 10, Exceptional, (146 reviews)
"The bed was fantastic. Perfect for a couple of days in Key West. "
United States
Amanda R.
The price is AED 350
AED 950 total
includes taxes & fees
19 May - 20 May
FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!
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