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

Find Historic Hotels in Sugarloaf Key, FL from CA $209

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Check availability on Sugarloaf Key Historic Hotels

Tonight
Aug 14 - Aug 15
Tomorrow
Aug 15 - Aug 16
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Sugarloaf Key historic hotels

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
CA $123
CA $209 total
includes taxes & fees
Aug 31 - Sep 1
Pegasus International Hotel

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
CA $276
CA $311 total
includes taxes & fees
Sep 15 - Sep 16
Amsterdam's Curry Mansion Inn

3. 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.
CA $143
CA $371 total
includes taxes & fees
Aug 16 - Aug 17
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

4. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Old Town Key West
United States
Jeanine
CA $180
CA $439 total
includes taxes & fees
Aug 31 - Sep 1
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

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.
CA $153
CA $401 total
includes taxes & fees
Aug 24 - Aug 25
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

6. FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Diane D.
CA $144
CA $373 total
includes taxes & fees
Aug 16 - Aug 17
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

7. 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.
CA $142
CA $368 total
includes taxes & fees
Aug 17 - Aug 18
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!

8. 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
CA $143
CA $371 total
includes taxes & fees
Aug 16 - Aug 17
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9. 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
United States
Warren K.
CA $144
CA $373 total
includes taxes & fees
Aug 16 - Aug 17
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

10. 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.
CA $144
CA $373 total
includes taxes & fees
Aug 17 - Aug 18
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
View all properties

Top Sugarloaf Key Hotel Reviews

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Beautiful property."
Jeff 1-night trip
Posted 1 hour ago
Hyatt Centric Key West Resort and Spa
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Pool area was great along with the bar. Free shuttle to Duval St was very handy"
Stephen 4-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Don’t read the bad reviews imo it’s just people who are not happy the property is exactly what it is. It could use a some touch ups but besides that it was excellent the shuttle drivers besides one guy were all very helpful the desk was helpful pool was beautiful room was huge with amazing view into the gulf I will be staying here again"
Jeffrey 7-night trip
Posted 4 hours ago
Beachside Resort & Residences
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Beautiful beach, helpful staff"
Cynthia 2-night trip
Posted 4 hours ago
Pier House Resort & Spa
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"This is our second trip to the Keys this year, and first time at this property. We found our home away from home and will stay here again next time! Everything is quality!"
Annie 3-night trip
Posted 4 hours ago
Hyatt Vacation Club at Windward Pointe, Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"Older resort but still nice, clean. The sargassum was in full force and the smell was very unpleasant but not the resorts fault. Amenities provided were nice. Pool area bars close way to early, adult only pool doesn’t have drinks available without walking. To neighboring pool. Close to sightseeing areas, shopping and dining options."
Heath 4-night trip
Posted 6 hours ago
Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Love the Music at the adult pool, it didn't stink that much from the seaweed. No smell by the pool. Love the firepits by the beach and food"
maria 1-night trip
Posted 8 hours ago
Casa Marina Key West, Curio Collection by Hilton
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"We love the ambiance and quiet adults only pool. The shuttle to and from downtown and the beach is also wonderful. The staff are friendly and accommodating."
Cara 4-night trip
Posted 9 hours ago
Parrot Key Hotel & Villas
Southwinds Motel

Southwinds Motel

8/10 Good
"Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location."
Tracy 4-night trip
Posted 9 hours ago
Southwinds Motel

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