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

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

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Check availability on Sugarloaf Key Luxury Hotels

Tonight
15 Sept - 16 Sept
Tomorrow
16 Sept - 17 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

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 breakfast setting with a table, chairs, a vase with flowers, and a city view.
A marina with numerous boats docked, a swimming pool, and palm trees.

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.
€155
includes taxes & fees
22 Sept - 23 Sept
Hilton Key West Resort & Marina
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

2. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
€185
includes taxes & fees
23 Sept - 24 Sept
The Perry Hotel & Marina Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.
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.

3. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
€130
includes taxes & fees
27 Sept - 28 Sept
DoubleTree Resort by Hilton Grand Key - Key West
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
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 hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

4. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
€155
includes taxes & fees
16 Sept - 17 Sept
Blue Flamingo Resort Key West
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A tall palm tree with a white building in the background.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

5. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
€175
includes taxes & fees
22 Sept - 23 Sept
Parrot Key Hotel & Villas
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
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.

6. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
€227
includes taxes & fees
28 Sept - 29 Sept
Margaritaville Beach House 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 resort with a pool leading to a beach, surrounded by palm trees and white buildings.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

7. 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.
€279
includes taxes & fees
22 Sept - 23 Sept
Casa Marina Key West, Curio Collection by Hilton
A covered porch with white railings, a ceiling fan, and a table with chairs.
A bedroom with a wooden headboard, a bed with white bedding, a blue patterned throw, and a view through a window with blinds.
A room with a wooden floor, a sofa with patterned cushions, a table, a chair, a lamp, and a window with blinds.
A tree with green foliage and red flowers.

8. The Porch on Frances Inn

The Porch on Frances Inn
Old Town Key West
€140
includes taxes & fees
16 Sept - 17 Sept
The Porch on Frances Inn
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

9. Eden House

Eden House
Key West Historic District
€112
includes taxes & fees
11 Oct - 12 Oct
Eden House
A beach with a wooden pier, palm trees, and beach umbrellas.
An outdoor dining area with tables and chairs, overlooking the ocean.
A modern bar area with a central island, white bar stools, and a view of the ocean.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

10. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
€236
includes taxes & fees
29 Sept - 30 Sept
The Reach Key West, Curio Collection by Hilton
View all properties

Top Sugarloaf Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The resort is very nice. Enjoyed the pool bar in the evenings. The pool was too warm so not very refreshing. Wished there was a microwave in the room."
Amy 3-night trip
Posted 11 hours ago
Casa Marina Key West, Curio Collection by Hilton
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Everything was great, food was wonderful"
Jamie 2-night trip
Posted 11 hours ago
Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"It was beautiful. I didn’t like the $60 amenity fee or $50 parking but it was very nice"
Carlos 2-night trip
Posted 12 hours ago
Southernmost Beach Resort and Guesthouses
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Muy buenos"
Caridad 1-night trip
Posted 13 hours ago
Hampton Inn Key West FL
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"We loved our room! It was clean and comfortable. The swimming pool was excellent. The hotel staff were super helpful and friendly. We would come back here and bring our kids next time!"
Mary Elizabeth 4-night trip
Posted 14 hours ago
Hyatt Vacation Club at Windward Pointe, Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Clean hotel, clean room, staff was very friendly. We would definitely stay here again!"
Sherill 2-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West

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