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

Historic Hotels & Resorts in Sugarloaf Key from NZ$324

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Check availability on Sugarloaf Key Historic Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 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 grand hallway with ornate ironwork, a chandelier, and a wooden floor.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.

1. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
NZ$396
includes taxes & fees
30 Sept - 1 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 living room with a sofa, armchair, coffee table, and a cabinet with decorative items.

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
NZ$913
includes taxes & fees
30 Sept - 1 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 bar area with a Pegasus International Hotel sign, round tables, and metal chairs.
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
NZ$324
includes taxes & fees
8 Oct - 9 Oct
Pegasus International Hotel
A covered outdoor area with wicker furniture and a pool.
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.
A wooden staircase with a view of greenery outside.

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
NZ$484
includes taxes & fees
30 Sept - 1 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 narrow pathway leading to a house with a blue exterior, a number '12' sign, and various potted plants.
A well-lit bedroom with a large bed, a desk, a chair, and a sofa. There are multiple pillows, a lamp, and a plant on the bedside table.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
NZ$613
includes taxes & fees
30 Sept - 1 Oct
Studio Blu - Historic Key West Studio + Bikes
A covered outdoor deck with wicker furniture and a white railing.
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.
A beach with palm trees and a clear sky.

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.
NZ$486
includes taxes & fees
30 Sept - 1 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 covered outdoor deck with wicker furniture and a white railing.
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.
NZ$484
includes taxes & fees
30 Sept - 1 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.
A covered outdoor area with wicker furniture and a pool.
A wooden staircase with a view of greenery outside.

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.
NZ$494
includes taxes & fees
30 Sept - 1 Oct
FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!
A covered outdoor area with wicker furniture and a pool.
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.
A wooden staircase with a view of greenery outside.

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.
NZ$484
includes taxes & fees
30 Sept - 1 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 covered porch with white railings and wicker furniture.
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.
A narrow pathway flanked by white picket fences and a tree with pink flowers.

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.
NZ$719
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

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 less than an hour ago
Casa Marina Key West, Curio Collection by Hilton
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"This place was amazing for the private beach front attached to our room. It feels a little older with limited in room amenities but with a restaurant bar attached to the hotel, private beach access, pool, and under 10 minute driver to Duval Street couldny have asked for a better stay."
Michael 3-night trip
Posted 1 hour ago
Ibis Bay Beach Resort
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Shuttle bus to central areas. Staff were great"
Shirley 2-night trip
Posted 2 hours ago
Beachside Resort & Residences
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"n"
Luis 1-night trip
Posted 2 hours ago
Hampton Inn Key West FL
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."
David John 5-night trip
Posted 6 hours ago
Southernmost Beach Resort and Guesthouses
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 20 hours ago
Hyatt Centric Key West Resort and Spa
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Hotel is very conveniently located to old town Key West. The renovations that have been made to the hotel really make it a very fun place to stay."
Bryan 3-night trip
Posted 1 day ago
La Concha Key West, Autograph Collection
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 1 day ago
Hilton Garden Inn Key West / The Keys Collection
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Close to everything, comfortable stay"
Nancy 2-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West

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