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 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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
P10,549
P16,478 total
includes taxes & fees
Oct 28 - Oct 29
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 couple holding hands in a tropical setting with palm trees and greenery.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
P7,867
P12,388 total
includes taxes & fees
Oct 26 - Oct 27
Blue Flamingo Resort Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A balcony with a view of the ocean, a sofa, and a massage table.
A resort with a beach, a dock, and a water view.

3. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
William N
P16,834
P23,336 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
Jennifer
P16,015
P22,415 total
includes taxes & fees
Oct 19 - Oct 20
Hyatt Centric Key West Resort and Spa
A swimming pool with lounge chairs, palm trees, and a small building.
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.

5. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Richard
P12,863
P18,446 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 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.
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
P16,331
P20,500 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 covered outdoor seating area with a pool in the background.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

7. Havana Cabana at Key West

Havana Cabana at Key West
New Town
United States
Stephanie
P9,143
P14,290 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 hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.
A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Nancy
P7,516
P10,583 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
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.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

9. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Charlene
P13,577
P19,519 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 beach with palm trees, lounge chairs, and umbrellas.
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.

10. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
P9,584
P14,400 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 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.
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
P8,817
P13,807 total
includes taxes & fees
Oct 31 - Nov 1
The Perry Hotel & Marina Key West
A two-story building with a covered entrance, palm trees, and a bench outside.
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.'
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
P12,611
P17,379 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 waterfront hotel with multiple balconies, a dock, and boats.
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.
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
P16,331
P20,855 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 marina with numerous boats docked, a swimming pool, and palm trees.
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
P7,693
P12,334 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Key West Resort & Marina
A pool area with lounge chairs and a cabana.
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.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

15. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Patrick
P18,853
P26,317 total
includes taxes & fees
Oct 20 - Oct 21
Ocean Key Resort - A Noble House Resort
A beach with a wooden pier, palm trees, and beach umbrellas.
A modern bar area with a central island, white bar stools, and a view of the ocean.
An outdoor dining area with tables and chairs, overlooking the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

16. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Darlene
P9,594
P15,049 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 marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

17. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
United States
Lynne
P11,873
P17,329 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 pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
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
P7,653
P9,643 total
includes taxes & fees
Oct 18 - Oct 19
Eden House
A pool area with lounge chairs 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.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

19. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
P18,803
P25,398 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 bar area with a counter, chairs, and a clock.
A couple walking along a poolside pathway surrounded by lush greenery.
A colonial-style building with a porch, surrounded by lush tropical vegetation.

20. The Gardens Hotel

The Gardens Hotel
Old Town Key West
United States
Gisele
P21,209
P23,861 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

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"The perfect place to stay! Quiet, great soft music at the outside bar that we could hear on the private beach. Close to everything. Helpful staff. Only thing is itโ€™s very expensive."
Lisa 6-night trip
Posted 2 hours ago
Pier House Resort & Spa
Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"Great property, very clean and great friendly staff. Pool and bar was awesome."
Scott 3-night trip
Posted 3 hours ago
Havana Cabana at 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 4 hours ago
Margaritaville Beach House Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"The resort staff was welcoming upon our arrival and the check-in process was efficient. Throughout our stay the members of your concierge service were extremely helpful, even proactively looking for and directing us to a beach that was clear of sargassum. The shuttle service was amazing with a great schedule."
Lawrence 3-night trip
Posted 6 hours ago
DoubleTree Resort by Hilton Grand Key - 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
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"Waterfront Parking cost"
Richard 2-night trip
Posted 2 days ago
Opal Key Resort & Marina, Key West

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 P9,643
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.