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

Find 4 Star Hotels in Sugarloaf Key, FL from ￥24,167

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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 room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

1. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
United States
Jacob Stuart
￥27,543
￥42,542 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost Beach Resort and Guesthouses
Pool
A couple holding hands in a tropical setting with palm trees and greenery.
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.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
￥19,768
￥31,130 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 balcony with a view of the ocean, a sofa, and a massage table.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

3. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
William N
￥41,001
￥57,153 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 beach wedding setup with white chairs, a wooden arch, and lanterns.
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.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
Joseph
￥40,137
￥56,176 total
includes taxes & fees
Oct 19 - Oct 20
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 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.
A person standing by a window overlooking a beach with palm trees and the ocean.

5. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Siamak
￥32,236
￥46,227 total
includes taxes & fees
Oct 30 - Oct 31
Margaritaville Beach House Key West
A multi-story hotel with a pink facade, multiple balconies, and a prominent 'LA CONCHA' sign.
A balcony with a sofa, a round table, and a view of the cityscape.
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 modern hotel entrance with a black and white striped curtain, wicker furniture, potted plants, and a sign for the Autograph Collection.

6. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Key West Historic District
United States
THOMAS
￥40,927
￥51,376 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 cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.

7. Havana Cabana at Key West

Havana Cabana at Key West
New Town
United States
Stephanie
￥22,766
￥35,652 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 modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.
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
￥18,836
￥26,524 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 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.
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
United States
Charlene
￥34,115
￥49,046 total
includes taxes & fees
Oct 25 - Oct 26
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 beach with palm trees, a sandy shore, and a calm sea under a clear sky.
A tall palm tree with a white building in the background.

10. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
￥24,019
￥36,089 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 balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
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.

11. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
￥17,573
￥29,408 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina Key West
A two-story building with a covered entrance, palm trees, and a bench outside.
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.'
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.

12. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
United States
Elizabeth
￥31,604
￥43,555 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 covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.

13. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Susan
￥40,927
￥52,267 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 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.
A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

14. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Eric A
￥19,307
￥30,964 total
includes taxes & fees
Oct 27 - Oct 28
Hilton Key West Resort & Marina
A pool area with lounge chairs and a cabana.
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.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

15. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Patrick
￥47,248
￥65,954 total
includes taxes & fees
Oct 18 - Oct 19
Ocean Key Resort - A Noble House Resort
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.
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.

16. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Darlene
￥24,055
￥37,734 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
￥29,755
￥43,430 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 spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

18. Eden House

Eden House
Key West Historic District
United States
Michelle
￥19,180
￥24,167 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 neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

19. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
￥47,248
￥63,820 total
includes taxes & fees
Oct 27 - Oct 28
Santa Maria Suites
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A couple walking along a poolside pathway surrounded by lush greenery.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.
A bar area with a counter, chairs, and a clock.

20. The Gardens Hotel

The Gardens Hotel
Old Town Key West
United States
Gisele
￥53,154
￥59,798 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

8/10 Good
"👍"
Peter 1-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses
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 4 hours ago
Havana Cabana at Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"This resort has everything with the best hospitality! I highly recommend this resort for anyone that wants to enjoy Key West with total relaxation! 😎"
Nikki 5-night trip
Posted 5 hours ago
Pier House Resort & Spa
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 10 hours ago
Opal Key Resort & Marina, Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"Very nice and friendly staff. It was a great place."
Siamak 3-night trip
Posted 11 hours ago
Margaritaville Beach House 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 1 day 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.
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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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