A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Key Historic Hotel

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Sugarloaf Key Historic Hotel

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Sugarloaf Key historic hotels

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
HK$646
HK$1,124 total
includes taxes & fees
31 Aug - 1 Sept
Pegasus International Hotel

2. CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Old Town Key West
United States
Anthony
HK$768
HK$2,053 total
includes taxes & fees
30 Aug - 31 Aug
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

3. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
HK$1,450
HK$1,632 total
includes taxes & fees
31 Aug - 1 Sept
Amsterdam's Curry Mansion Inn

4. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
United States
Jeanine
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

5. 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
United States
Emily F.
HK$1,142
HK$2,633 total
includes taxes & fees
31 Aug - 1 Sept
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

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

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Old Town Key West
United States
Ashley S.
HK$768
HK$2,053 total
includes taxes & fees
30 Aug - 31 Aug
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

7. 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
United States
Jeffrey M.
HK$768
HK$2,053 total
includes taxes & fees
30 Aug - 31 Aug
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

8. ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!

ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!
Old Town Key West
United States
Maryanne
HK$815
HK$2,121 total
includes taxes & fees
14 Sept - 15 Sept
ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!

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

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Old Town Key West
United States
Christina
HK$768
HK$2,053 total
includes taxes & fees
3 Sept - 4 Sept
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

10. HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!
Old Town Key West
United States
JUANITA R.
HK$800
HK$2,096 total
includes taxes & fees
29 Sept - 30 Sept
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!
View all properties

Top Sugarloaf Key Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Stayed for 1 night while traveling. Was very clean and comfortable. Staff were very friendly and helpful. We enjoyed the pool. Free breakfast the next morning was great."
emily 1-night trip
Posted 10 hours ago
Hampton Inn Key West FL
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"Great location, friendly staff"
Joseph 4-night trip
Posted 17 hours ago
The Reach Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Room was very clean, pool was great! Bravin and Billy at the pool bar are the best! This was our second stay and will definitely be back soon!"
Kyle M 6-night trip
Posted 17 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"We stayed here for our honeymoon! Staff was very friendly and helpful. Restaurants on property had great food and atmosphere."
Logan 4-night trip
Posted 17 hours ago
Casa Marina Key West, Curio Collection by Hilton
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"So spacious, perfect for groups. The room was very clean and the staff were helpful! 10/10 would stay again They were doing what seemed like a clorox cleaning of the common area sidewalks, which I thought would have been better scheduled during a week day when there werent many guests but other than that the stay was perfect"
nicole 1-night trip
Posted 17 hours ago
Parrot Key Hotel & Villas
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"I was confused on the breakfast so I don’t think I got breakfast once and I couldn’t find my room at fist so that was a lot to figure out I was nervous cause I was traveling alone mostly everything else was great though"
Tonya 5-night trip
Posted 18 hours ago
Blue Flamingo Resort Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"i stayed in the king room with accessible lanai. the bathroom was spacious, easily accessible shower stall. i liked the bar near the private beach, the food and drinks were good. i had delicious filet mignon for dinner, for breakfast which was included i had the spectacular lobster benedict, soooo delicious. i’ll stay here again, it’s right on Duval street, walking distance to the bars and shops and boating trips, jet ski rentals"
Steven 2-night trip
Posted 2 days ago
Pier House Resort & Spa
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Beautiful updated hotel, loved the bar and the lobby . Our room was perfect after we moved to the 6th floor . The first room was not great . We liked the newer section much better . Loved the bikes and the location. Elevators need to be updated and they need to add another one . Would stay here again ."
lisa 4-night trip
Posted 2 days ago
La Concha Key West, Autograph Collection

Explore a world of travel with Expedia