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

Find 4 Star Hotels in Sugarloaf Key, FL from $93

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Check availability on Sugarloaf Key 4 Star Hotels

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Sep 1 - Sep 2
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Sep 2 - Sep 3
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Sep 4 - Sep 6
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Sep 11 - Sep 13

Our top choices for Sugarloaf Key 4-star hotels

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 beachside lounge with chairs and umbrellas, overlooking the ocean.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beachfront resort with a prominent sign, white balconies, and tropical landscaping.

1. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
United States
Deaenna
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
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 marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

2. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
FRANK
$263 nightly
$296 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
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.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

3. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Melvin
$214 nightly
$241 total
Sep 14 - Sep 15
Total with taxes and fees
Parrot Key Hotel & Villas
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 beach with clear turquoise water, snorkelers, and a large building in the background.

4. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Key West Historic District
United States
Fatima
$219 nightly
$246 total
Sep 2 - Sep 3
Total with taxes and fees
La Concha Key West, Autograph Collection
A hotel with a large pool, multiple balconies, and palm trees.
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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

5. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Sabrina
$160 nightly
$180 total
Sep 2 - Sep 3
Total with taxes and fees
Blue Flamingo Resort Key West
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.

6. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
TRICIA LYNN
$234 nightly
$263 total
Sep 15 - Sep 16
Total with taxes and fees
Margaritaville Beach House Key West
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.
An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.
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 Kingdom
Fabrizio
$166 nightly
$187 total
Sep 17 - Sep 18
Total with taxes and fees
Havana Cabana at 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 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.

8. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Dirk
$272 nightly
$306 total
Sep 13 - Sep 14
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
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 pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A balcony with a view of the ocean, a sofa, and a massage table.

9. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
Mark
$313 nightly
$352 total
Sep 23 - Sep 24
Total with taxes and fees
Pier House Resort & Spa
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
An outdoor seating area with tables and chairs, overlooking a marina with boats.
A marina with numerous yachts docked, surrounded by palm trees and a clear sky.

10. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Boyan
$199 nightly
$224 total
Sep 21 - Sep 22
Total with taxes and fees
The Perry Hotel & Marina Key West
A beach with a wooden pier, palm trees, and beach umbrellas.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
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.

11. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
United States
Joseph
$242 nightly
$272 total
Sep 28 - Sep 29
Total with taxes and fees
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 covered outdoor area with a pool, palm trees, and lounge chairs.

12. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
United States
Danny Lee
$238 nightly
$267 total
Sep 13 - Sep 14
Total with taxes and fees
The Marker Key West Harbor Resort
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
An outdoor patio with tables and chairs, umbrellas, and palm trees.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.
A hotel with a central courtyard, palm trees, and a fountain.

13. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Jose
$144 nightly
$162 total
Sep 8 - Sep 9
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
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 restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

14. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Melissa
$294 nightly
$331 total
Sep 2 - Sep 3
Total with taxes and fees
Opal Key Resort & Marina, Key West
A hotel room with a balcony overlooking a marina and the ocean.
A marina with numerous boats docked, a swimming pool, and palm trees.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

15. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Linda
$167 nightly
$188 total
Sep 8 - Sep 9
Total with taxes and fees
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 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.

16. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Brian
$323 nightly
$364 total
Sep 27 - Sep 28
Total with taxes and fees
Ocean Key Resort - A Noble House Resort
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 picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.

17. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
United States
Stacey
$260 nightly
$293 total
Sep 2 - Sep 3
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
A pool area with lounge chairs and palm trees.
A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.
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.

18. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
June Young
$339 nightly
$381 total
Sep 2 - Sep 3
Total with taxes and fees
Santa Maria Suites
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 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.

19. Eden House

Eden House
Key West Historic District
United States
Therese
$83 nightly
$93 total
Sep 27 - Sep 28
Total with taxes and fees
Eden House
A pool area with lounge chairs, a pool with a depth limit sign, and a building with balconies.
A hotel room with a bed, a desk, a television, and a view of the outdoors through a sliding door.
A beach with a palm tree and the sun setting over the ocean.
A narrow wooden pathway leading to a door, a fire alarm box, and a lattice fence.

20. Bishop Hotel Key West

Bishop Hotel Key West
Old Town Key West
United States
tracy
Bishop Hotel Key West
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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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Staff was very helpful and the location is great plus the free shuttle service is great 👍 and there are very helpful"
Doris 3-night trip
Posted 10 hours ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."
Quantona 3-night trip
Posted 22 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Best Hotel in the Key West. Room was very clean, best staff services. Beautiful beach view and breakfast was delicious. My husband and I love this place. 💯 recommend."
Vivian 1-night trip
Posted 2 days ago
Pier House Resort & Spa
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"Had an issue with the door on the last day, but they rectified the problem. Stay was quite pleasant. Enjoyed immensely will be back in January."
Clay 4-night trip
Posted 3 days ago
The Reach Key West, Curio Collection by Hilton
Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"This hotel is beautiful, and the service is outstanding. From the moment you approach the front desk, they offer you a drink. I've been encouraging all my friends to visit. I can't wait to return and stay for a few days longer!"
Karen 1-night trip
Posted 4 days ago
Margaritaville Beach House Key West

Find out more about Sugarloaf Key

Sugarloaf Key Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Sugarloaf Key, Summerland Key are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Sugarloaf Key 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Sugarloaf Key. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Sugarloaf Key, Summerland Key, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Sugarloaf Key hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Sugarloaf Key?
We can help you quickly locate the ideal 4-star hotel for your vacation in Sugarloaf Key. Use our handy filter tool to tailor your search by things like budget, amenities and star rating and get access to terrific deals in a few clicks.
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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 escape by choosing a 4-star hotel. As well as featuring upscale accommodations, these retreats are typically packed with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your trip an even more lavish and special one. Round-the-clock concierge assistance, luxurious spas and gourmet dining are just the start of the superior conveniences and services you'll likely get access to.
Does Sugarloaf Key have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next getaway in Sugarloaf Key where everything is taken care of, from your room to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this popular destination.

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