Find Historic Hotels in Sugarloaf Key, FL

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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, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is AED 661
AED 1,190 total
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to Key West!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very Good, (121 reviews)
"Great experience "
United States
Peyton S.
The price is AED 1,286
AED 2,559 total
includes taxes & fees
22 Feb - 23 Feb
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is AED 1,377
AED 2,674 total
includes taxes & fees
21 Feb - 22 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is AED 909
AED 1,620 total
includes taxes & fees
12 Feb - 13 Feb
Cottage with Pool and Dockage, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (122 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is AED 826
AED 1,516 total
includes taxes & fees
15 Feb - 16 Feb
Charming cottages, dockage, pool, just minutes to Key West

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, (136 reviews)
"Quaint and quiet, clean and lovely place. Would recommend a key code lock for guests only on front door and gates for security but we had no issues. Pool heated, amenities provided as described. "
United States
Michelle
The price is AED 1,579
AED 2,510 total
includes taxes & fees
10 Mar - 11 Mar
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1,008 reviews)
"Very clean, great amenities! "
United States
Heather
Pegasus International Hotel

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is AED 1,506
AED 2,840 total
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

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, (118 reviews)
"Brilliant location… very generous to leave bikes and chairs which was used every day. Well decorated and equipped room and comfy bed . Shower is hot and has great water pressure . Check in and out is easy . Thank you "
United Kingdom
Simon
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Grand Maloney Hotel

Grand Maloney Hotel
2.0 star property
Key West Historic District
7.8 out of 10, Good, (13 reviews)
"Excellent location in old town. Quiet room away from street. "
United States
James
The price is AED 1,393
AED 2,196 total
includes taxes & fees
11 Feb - 12 Feb
Grand Maloney Hotel
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