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

Search Historic Hotels in Sugarloaf Key

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Check availability on Sugarloaf Key Historic Hotels

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

1. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
£120
includes taxes & fees
5 Oct - 6 Oct
Amsterdam's Curry Mansion Inn

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
£406
includes taxes & fees
1 Oct - 2 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

3. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
£130
includes taxes & fees
1 Oct - 2 Oct
Pegasus International Hotel

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
£213
includes taxes & fees
1 Oct - 2 Oct
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
£275
includes taxes & fees
6 Oct - 7 Oct
Studio Blu - Historic Key West Studio + Bikes

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.
£209
includes taxes & fees
8 Oct - 9 Oct
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!

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.
£216
includes taxes & fees
7 Oct - 8 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

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.
£226
includes taxes & fees
8 Oct - 9 Oct
FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!

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.
£218
includes taxes & fees
4 Oct - 5 Oct
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!

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.
£313
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

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Pros - The room was beautiful! Very clean and felt like a home away from home. Basically, a fully furnished condo with everything you'd need in the kitchen if you're the type to cook on vacation. Covered parking was a plus! Hourly shuttle to the Duval Street area provided which saves $$$ on parking! Cons - Walkway area around pool has many loose and raised blocks that were a tripping hazard. Beach is a bit small and if it's sunsets you're looking for, they are best viewed at the other end of the island. Front desk staff, while friendly, left out important info (such as availability of shuttle and pool bar hours). For first time visitors, signage is non-existent as far as where the check-in lobby is (no sign outside saying such, either) and the way the property is configured, it's not an easy determination. Certainly not complaining as we had a great time. Just offering our experience and observations."
Scott 3-night trip
Posted 1 hour 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 13 hours ago
Parrot Key Hotel & Villas
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Good service"
rolando 3-night trip
Posted 14 hours ago
Ibis Bay Beach Resort
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 14 hours ago
Winslow's Bungalows - Key West Historic Inns
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 15 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 16 hours ago
Casa Marina Key West, Curio Collection by Hilton
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 22 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 2 days 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 2 days ago
La Concha Key West, Autograph Collection

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