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

Sugarloaf Key Historic Hotel

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Check availability on Sugarloaf Key Historic Hotel

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Sugarloaf Key historic hotels

A wooden boardwalk leading to a beach with palm trees and a clear sky.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

1. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
HK$1,130
HK$1,271 total
includes taxes & fees
5 Oct - 6 Oct
Amsterdam's Curry Mansion Inn
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A two-story house with a front porch, a staircase, and a garage.
A bar with a signboard listing various destinations.
A pathway through a lush garden with various plants and trees.

2. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
United States
Linda
HK$2,401
HK$4,976 total
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A balcony with a view of a street, a bench, and a potted plant.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A multi-story building with a ground-level commercial space featuring a brightly lit storefront.
A hotel lobby with a bar area, seating, and a fireplace.

3. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
HK$927
HK$1,440 total
includes taxes & fees
4 Oct - 5 Oct
Pegasus International Hotel
A covered outdoor area with wicker furniture and a pool.
A beach with palm trees and a clear sky.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

4. COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!

COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
Old Town Key West
United States
Patrick
HK$855
HK$2,160 total
includes taxes & fees
8 Oct - 9 Oct
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
A compact kitchen with a microwave, oven, and sink. There is a small dining table with a bowl and a chair. The kitchen has light blue tiles and wooden cabinets.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A narrow pathway leading to a house with a blue exterior, a number '12' sign, and various potted plants.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
HK$1,272
HK$2,781 total
includes taxes & fees
5 Oct - 6 Oct
Studio Blu - Historic Key West Studio + Bikes
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A wooden staircase with a view of greenery outside.

6. CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
Old Town Key West
United States
Darcie B.
HK$769
HK$2,063 total
includes taxes & fees
4 Oct - 5 Oct
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
A living room with two sofas, a coffee table, and a window with blinds.
A beach with palm trees and a clear sky.
A wooden staircase with a view of greenery outside.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

7. HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
Old Town Key West
United States
Ron C.
HK$855
HK$2,160 total
includes taxes & fees
8 Oct - 9 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A covered outdoor deck with wicker furniture and a white railing.
A wooden staircase with a view of greenery outside.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A beach with palm trees and a clear sky.

8. FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!

FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!
Old Town Key West
United States
Emily K.
HK$996
HK$2,342 total
includes taxes & fees
8 Oct - 9 Oct
FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!
A covered outdoor area with wicker furniture and a pool.
A wooden staircase with a view of greenery outside.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

9. FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Jake H.
HK$824
HK$2,132 total
includes taxes & fees
3 Oct - 4 Oct
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
A beach with people sunbathing and swimming, a clear blue sky, and a calm sea.
A compact kitchen with a microwave, refrigerator, and a sink.
A narrow pathway flanked by white picket fences and a tree with pink flowers.
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.

10. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
United States
Michael R.
HK$1,116
HK$3,205 total
includes taxes & fees
6 Oct - 7 Oct
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
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Top Sugarloaf Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Had a great time!"
Nathan 4-night trip
Posted 2 hours ago
Winslow's Bungalows - Key West Historic Inns
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We like it"
Jeffrey 3-night trip
Posted 3 hours ago
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The room was clean. No daily housekeeping. The staff were pleasant and quiet helpful. Breakfast was outstanding. It was alacart and you have to pay per item. Over all this was the most relaxing vacation I've been on. Loved it!"
Harry 1-night trip
Posted 8 hours ago
Beachside Resort & Residences
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted 23 hours ago
Parrot Key Hotel & Villas
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"This is our 8th stay at The Hampton Inn key west. Great property, awesome staff especially Kim at the front desk. Very clean property and nice rooms .we always stay ocean front, beautiful view, peaceful.Cant wait to go again."
Beverly 3-night trip
Posted 1 day ago
Hampton Inn Key West FL
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Amazing place to stay for vacation."
David 5-night trip
Posted 1 day ago
Casa Marina Key West, Curio Collection by Hilton
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"
Christy 2-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Thank you"
Agustin 2-night trip
Posted 2 days ago
Hilton Garden Inn Key West / The Keys Collection

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