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

Sugarloaf Key Hotel Guide - Historic Hotels in Sugarloaf Key, Summerland Key

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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 large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.

1. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
€144
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 bar with a signboard listing various destinations.
A two-story house with a front porch, a staircase, and a garage.
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
€512
includes taxes & fees
1 Oct - 2 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
€153
includes taxes & fees
1 Oct - 2 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 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
€248
includes taxes & fees
1 Oct - 2 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.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
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.
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.
€321
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.
€249
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 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.

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.
€248
includes taxes & fees
1 Oct - 2 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A covered outdoor deck with wicker furniture and a white railing.
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.

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.
€266
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 beach with palm trees and a clear sky.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

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.
€255
includes taxes & fees
4 Oct - 5 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 compact kitchen with a microwave, refrigerator, and a sink.
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.
€366
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
"The property offered striking beauty and an ideal location. The staff we spoke with throughout our stay were consistently friendly and welcoming. I appreciated the amenities. The complimentary continental breakfast and two welcome drinks were excellent. I would gladly return for another visit."
Lauren 1-night trip
Posted less than an hour ago
Winslow's Bungalows - Key West Historic Inns
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Beautiful"
orlando 2-night trip
Posted less than an hour ago
Beachside Resort & Residences
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 2 hours 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 2 hours 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 3 hours ago
Ibis Bay Beach Resort
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 8 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 22 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

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