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

Sugarloaf Key 4 Stars Hotels

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Check availability on Sugarloaf Key 4 Star Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Sugarloaf Key 4-star hotels

A deck with sun loungers and a railing overlooking the sea.
A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

1. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
United States
Jacob Stuart
₩232,560
₩359,204 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost Beach Resort and Guesthouses
Pool
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
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 couple holding hands in a tropical setting with palm trees and greenery.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
₩166,915
₩262,832 total
includes taxes & fees
Oct 25 - Oct 26
Blue Flamingo Resort Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A resort with a beach, a dock, and a water view.
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.

3. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
William N
₩347,768
₩484,774 total
includes taxes & fees
Nov 2 - Nov 3
Pier House Resort & Spa
A hotel with a swimming pool, balconies, and a view of the sea.
A balcony with a view of the ocean, a table, chairs, and a railing.
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 marina with jet skis docked in front of a hotel with a dock and a boat in the background.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
Joseph
₩339,273
₩475,217 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Centric Key West Resort and Spa
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A person standing by a window overlooking a beach with palm trees and the ocean.
A beach with a palm tree and two chairs.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

5. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Siamak
₩277,524
₩396,391 total
includes taxes & fees
Oct 31 - Nov 1
Margaritaville Beach House Key West
A multi-story hotel with a pink facade, multiple balconies, and a prominent 'LA CONCHA' sign.
A beach with clear turquoise water, snorkelers, and a large building in the background.
A spacious lobby with a checkered floor, a central seating area with wicker chairs, a large potted plant, and a staircase with a metal railing.
A balcony with a sofa, a round table, and a view of the cityscape.

6. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Key West Historic District
United States
THOMAS
₩347,319
₩435,993 total
includes taxes & fees
Oct 25 - Oct 26
La Concha Key West, Autograph Collection
A swimming pool surrounded by palm trees and a natural rock formation.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

7. Havana Cabana at Key West

Havana Cabana at Key West
New Town
United States
Stephanie
₩193,104
₩302,396 total
includes taxes & fees
Nov 1 - Nov 2
Havana Cabana at Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Nancy
₩159,043
₩223,954 total
includes taxes & fees
Oct 25 - Oct 26
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 beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

9. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Charlene
₩288,065
₩414,135 total
includes taxes & fees
Nov 1 - Nov 2
Casa Marina Key West, Curio Collection by Hilton
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.
A tall palm tree with a white building in the background.
A beach with palm trees, lounge chairs, and umbrellas.

10. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
₩202,806
₩304,716 total
includes taxes & fees
Oct 29 - Oct 30
Parrot Key Hotel & Villas
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 marina with boats docked, a swimming pool, and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

11. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
₩123,589
₩219,867 total
includes taxes & fees
Nov 2 - Nov 3
The Perry Hotel & Marina Key West
A two-story building with a covered entrance, palm trees, and a bench outside.
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.
A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.'

12. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
United States
Elizabeth
₩266,850
₩367,759 total
includes taxes & fees
Oct 18 - Oct 19
Winslow's Bungalows - Key West Historic Inns
A hotel with a covered entrance, multiple balconies, and palm trees.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A waterfront hotel with multiple balconies, a dock, and boats.

13. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Susan
₩345,571
₩441,317 total
includes taxes & fees
Oct 18 - Oct 19
Opal Key Resort & Marina, Key West
A marina with boats docked, a pool area, and a building with a white facade.
A covered outdoor seating area with tables and chairs, overlooking a marina with boats.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A clear view of turquoise ocean water and a blue sky with clouds.

14. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Eric A
₩163,019
₩261,450 total
includes taxes & fees
Oct 27 - Oct 28
Hilton Key West Resort & Marina
A pool area with lounge chairs and a cabana.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
A balcony with a table set for breakfast, overlooking the sea.

15. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Patrick
₩398,941
₩556,883 total
includes taxes & fees
Oct 18 - Oct 19
Ocean Key Resort - A Noble House Resort
A hotel room with a bed, a desk, a chair, a TV, a lamp, and a view of palm trees through the window.
A beach with a wooden pier, palm trees, and beach umbrellas.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

16. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Darlene
₩204,033
₩320,055 total
includes taxes & fees
Oct 26 - Oct 27
The Reach Key West, Curio Collection by Hilton
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A tropical setting with palm trees and a building with a white facade and dark roof.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

17. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
United States
Lynne
₩252,510
₩368,557 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
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.

18. Eden House

Eden House
Key West Historic District
United States
Michelle
₩174,335
₩219,662 total
includes taxes & fees
Oct 18 - Oct 19
Eden House
A pool area with lounge chairs and palm trees.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

19. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
₩398,941
₩538,871 total
includes taxes & fees
Oct 26 - Oct 27
Santa Maria Suites
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A bar area with a counter, chairs, and a clock.
A couple walking along a poolside pathway surrounded by lush greenery.

20. The Gardens Hotel

The Gardens Hotel
Old Town Key West
United States
Gisele
₩448,808
₩504,908 total
includes taxes & fees
Oct 27 - Oct 28
The Gardens Hotel
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Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colorful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkeling spots.

See all hotels in Sugarloaf Key
A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"."
Angela 3-night trip
Posted 3 hours ago
Southernmost Beach Resort and Guesthouses
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Staff is very friendly and helpful."
Tracy 4-night trip
Posted 3 hours ago
Pier House Resort & Spa
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"The property was well maintained and clean. The tropical plants and trees were beautiful and made it feel like a little oasis. Our room was clean and we had what we needed. The staff we interacted with were very friendly and welcoming. Breakfast was good and was just enough to get the day started. We enjoyed the bar and the pools and the welcome drink was a nice treat! Overall we had a great experience and we would recommend this place for the amenities and the location."
Jason 4-night trip
Posted 7 hours ago
Winslow's Bungalows - Key West Historic Inns
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"The staff is amazing. Super welcoming and they gave me a great layout of what the hotel had to offer. The wallet John was a class act I really appreciated his help particularly. I only went to 2 of the 4 pools but they were clean and relaxing. The food truck had some surprisingly good food, and the bar was good too. You can walk the little beach they have here, layout and relax in the hammocks, and if you want to hang in the room there is plenty in there as well. Location wise there is a Walgreens within walking distance and there are two large shopping plazas within a quarter of a mile so you have plenty of options for food or items for the room. The shuttle service to the beach and to Duval Street came in clutch as well. If you are looking for a place that is a little quieter to sleep at than Duval but close to the action this is the place. I will certainly stay here again when in the area."
Joshua 2-night trip
Posted 8 hours ago
Parrot Key Hotel & Villas
Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"So Pretty and clean the place"
andrea v 2-night trip
Posted 20 hours ago
Havana Cabana at Key West
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"The hotel location, cleanliness and view are awesome. No complaints about anything. The unlimited cold water bottles were icing on the cake. If I’m so happy with a partial sea view room, I’ll be even happier with an oceanfront room. Maybe next time."
Vivek 2-night trip
Posted 1 day ago
Opal Key Resort & Marina, Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Great property"
Charlene 3-night trip
Posted 2 days ago
Casa Marina Key West, Curio Collection by Hilton

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Sugarloaf Key?
With Expedia's handy search filters, scoring a top deal on a 4-star hotel in Sugarloaf Key just got simpler. Start by entering your chosen travel dates and length of your break. Then list the results by price and choose the option that best matches your budget and style.
  • Search for the lowest price from ₩219,662
What's the difference between 5-star and 4-star hotels in Sugarloaf Key?
Treat yourself to refined living during your Sugarloaf Key getaway by checking in to a 4-star hotel. As well as featuring upscale accommodations, these retreats are usually packed with amenities, including large beds, complimentary bathrobes and plenty more. A 5-star hotel will go above and beyond to make your stay an even more indulgent and special one. 24-hour concierge assistance, on-site spas and world-class dining are just the start of the superior services and conveniences you'll likely be able to enjoy.
Does Sugarloaf Key have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your dream hotel in Sugarloaf Key where just about everything is taken care of, from your meals to your accommodations, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.

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