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

4 Star Hotels in Sugarloaf Key, Summerland Key

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Check availability on Sugarloaf Key 4 Star Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Sugarloaf Key 4-star hotels

Pool
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.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

1. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Jesus
€167
includes taxes & fees
25 Oct - 26 Oct
Blue Flamingo Resort Key West
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.

2. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Siamak
€276
includes taxes & fees
25 Oct - 26 Oct
Margaritaville Beach House Key West
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 covered outdoor seating area with a pool in the background.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

3. Havana Cabana at Key West

Havana Cabana at Key West
New Town
United States
Stephanie
€220
includes taxes & fees
15 Nov - 16 Nov
Havana Cabana at Key West
A deck with sun loungers and a railing overlooking 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.
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.

4. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
United States
Jacob Stuart
€187
includes taxes & fees
25 Oct - 26 Oct
Southernmost Beach Resort and Guesthouses
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, lounge chairs, and umbrellas.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

5. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
€170
includes taxes & fees
25 Oct - 26 Oct
Parrot Key Hotel & Villas
A marina with boats docked, a pool area, and a building with a white facade.
A marina with numerous boats docked, a swimming pool, and palm trees.
A clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

6. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Eric A
€169
includes taxes & fees
26 Oct - 27 Oct
Hilton Key West Resort & Marina
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
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.
A resort with a beach, a dock, and a water view.

7. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
William N
€219
includes taxes & fees
26 Oct - 27 Oct
Pier House Resort & Spa
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.

8. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Ann
€295
includes taxes & fees
25 Oct - 26 Oct
Opal Key Resort & Marina, Key West
A pool area with lounge chairs and gazebos, surrounded by palm trees.
An outdoor bar area with a poolside view, featuring a bar counter, blue chairs, and a sign reading 'GUMBO LIMBO'.
A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view of buildings.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

9. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Danee
€148
includes taxes & fees
28 Oct - 29 Oct
DoubleTree Resort by Hilton Grand Key - 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 bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.

10. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
United States
Elizabeth
€246
includes taxes & fees
26 Oct - 27 Oct
Winslow's Bungalows - Key West Historic Inns
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.

11. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Jaime
€306
includes taxes & fees
1 Nov - 2 Nov
Casa Marina Key West, Curio Collection by Hilton
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.

12. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Key West Historic District
United States
THOMAS
€280
includes taxes & fees
25 Oct - 26 Oct
La Concha Key West, Autograph Collection
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 hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A reception area with a wooden reception desk, a tiled wall, and a hanging light fixture.

13. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Jeremy
€353
includes taxes & fees
23 Nov - 24 Nov
Ocean Key Resort - A Noble House Resort
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.

14. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Brett
€240
includes taxes & fees
26 Oct - 27 Oct
The Reach Key West, Curio Collection by Hilton
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 restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

15. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
€154
includes taxes & fees
16 Nov - 17 Nov
The Perry Hotel & Marina Key West
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 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.

16. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
Michael Joseph
€300
includes taxes & fees
25 Oct - 26 Oct
Hyatt Centric Key West Resort and Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A covered outdoor area with a pool, palm trees, and lounge chairs.
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
€240
includes taxes & fees
25 Oct - 26 Oct
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 gray sofa, wooden staircase, and a kitchen in the background.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

18. Eden House

Eden House
Key West Historic District
United States
Michelle
€171
includes taxes & fees
27 Oct - 28 Oct
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 reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

19. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
€360
includes taxes & fees
27 Oct - 28 Oct
Santa Maria Suites
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
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.
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
€225
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
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Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colourful 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 snorkelling 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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

8/10 Good
"Checkin was ok, staff were ok. Room was ok . Main bathroom sink was blocked and ensuite door was broken/off the tracks. Said they would look at it. Directly across the road from the beach. Free shuttle to and from Old Town. Very basic hotel for the price"
Belinda 1-night trip
Posted 4 hours ago
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Loved this hotel! Hourly shuttle to town, wish it was later then 10 pm though. Staff very nice and they celebrated my son’s birthday with champagne and snacks in our room!"
Melissa 3-night trip
Posted 7 hours ago
Blue Flamingo Resort Key West
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Proximity to downtown and perfect walking distance to restaurants. Great pool."
Hollie 4-night trip
Posted 7 hours ago
Opal Key Resort & Marina, Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"The resort was amazing. Staff was friendly and went out of their way to make you feel welcomed all week, not just when you checked in. The property was clean and the room was very comfortable. I would definitely go back."
Jennifer 5-night trip
Posted 8 hours ago
Winslow's Bungalows - Key West Historic Inns
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Parrot Key Hotel & Villas is the place to stay if you are planning a family trip to Key West on a reasonable budget.The rooms are spacious and very clean. Everybody is nice, we had no complaints. The restaurant is under construction at this time but in a few months I believe it will be up and running."
Natacha 1-night trip
Posted 16 hours ago
Parrot Key Hotel & Villas
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

8/10 Good
"We liked this property. However Building number 1 was totally under construction. Should be for some time. Therefore you should book the room of your choice in building number 3 to be away from the noise."
stephen 6-night trip
Posted 17 hours ago
Hilton Key West Resort & Marina

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 €148
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 accommodation, 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 accommodation, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.

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