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

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Check availability on Sugarloaf Key Luxury Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Sugarloaf Key luxury hotels

A marina with boats docked, a pool area, and a building with a white facade.
A hotel room with a balcony overlooking a marina and the ocean.
A marina with numerous boats docked, a swimming pool, and palm trees.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

1. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Waterfront luxury meets marina adventure at Key West resort with 6 pools and bayside elegance.
₩160,847
₩262,054 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Key West Resort & Marina
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A beach with a palm tree and two chairs.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

2. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
₩241,243
₩356,446 total
includes taxes & fees
Oct 7 - Oct 8
Margaritaville Beach House Key West
A pool area with lounge chairs and palm trees.
A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

3. Santa Maria Suites

Santa Maria Suites
Old Town Key West
  • Lavish Key West retreat features luxury suites, designer touches, 2 pools, and vibrant bar scene.
₩378,129
₩516,878 total
includes taxes & fees
Sep 27 - Sep 28
Santa Maria Suites
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

4. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
₩163,163
₩267,099 total
includes taxes & fees
Oct 8 - Oct 9
The Perry Hotel & Marina Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A balcony with a view of the ocean, a sofa, and a massage table.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

5. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
₩301,837
₩434,792 total
includes taxes & fees
Sep 30 - Oct 1
Pier House Resort & Spa
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.

6. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
₩160,129
₩256,381 total
includes taxes & fees
Sep 27 - Sep 28
Blue Flamingo Resort Key West
A hotel with a swimming pool, balconies, and a view of the sea.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

7. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
₩290,034
₩420,820 total
includes taxes & fees
Sep 28 - Sep 29
Hyatt Centric Key West Resort and Spa
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
An outdoor patio with tables and chairs, umbrellas, and palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
₩160,847
₩226,694 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree Resort by Hilton Grand Key - Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A spacious lobby with green sofas, a coffee table, and a dining area.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

9. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
  • Beachfront luxury graces historic Key West resort with private shore access and spa treatments.
₩322,199
₩454,627 total
includes taxes & fees
Sep 30 - Oct 1
Casa Marina Key West, Curio Collection by Hilton
A beach with a wooden pier, palm trees, and beach umbrellas.
An outdoor dining area with tables and chairs, overlooking the ocean.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

10. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
₩269,759
₩394,962 total
includes taxes & fees
Oct 5 - Oct 6
The Reach Key West, Curio Collection by Hilton
View all properties

Top Sugarloaf Key Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Very quiet and clean. Staff were excellent. Well appointed accommodation."
Norma 2-night trip
Posted 3 hours ago
Beachside Resort & Residences
Hampton Inn Key West FL

Hampton Inn Key West FL

8/10 Good
"Mi experiencia en Hampton Inn Key West fue muy buena. 👍🌴 El servicio fue excelente y recibimos muy buena atención durante nuestra estadía. Me gustó mucho que el hotel ofreciera transporte hasta la zona de Duval Street, lo cual fue muy conveniente para disfrutar de Key West sin preocuparnos por el estacionamiento. 🚌🌴 Las instalaciones estaban en excelentes condiciones y todo se sentía limpio y bien cuidado. La piscina también estuvo muy bien, aunque considero que el área podría tener un poco más de ambiente y entretenimiento para hacerla aún más atractiva. 🏊‍♂️☀️ Por el precio que pagamos en nuestra reserva, considero que fue una excelente opción y una muy buena relación calidad-precio. Definitivamente disfrutamos nuestra estadía. ⭐⭐⭐⭐⭐"
Brian 1-night trip
Posted 10 hours ago
Hampton Inn Key West FL
Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"La ubicacion es excelente, solo que el hotel esta un poco dejado, le falta cariño, pero el personal es muy atento y hemos tenido una muy buena estancia en Key West,"
Carlos 1-night trip
Posted 12 hours ago
Pier House Resort & Spa
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Our room was always clean with clean towels. The night person (Michelle) was very personable! The only thing that was an inconvenient was the elevator being out of order to where out room was. It was a long walk for me to go to the other side to get in the elevator. My legs don't work very well. It was like that for 3 days"
Dolores 7-night trip
Posted 14 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The facility was beautiful and the amenities were great! just keep in mind it is a walk to the seaport and the main part of Duval, which became a little too far to walk back in forth, which we knew it would be a walk when we booked it."
Darlene 2-night trip
Posted 14 hours ago
Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate the other sister options to eat but that was ok. Food was very tasty. Beds were comfortable and pillows were firm and soft, great options, mini fridge and coffee w/water in the room, oh and the ear plugs were so cute!!!"
Tristy 4-night trip
Posted 17 hours ago
Blue Flamingo Resort Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 3 days ago
Ibis Bay Beach Resort

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