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

Find 4 Star Hotels in Sugarloaf Key, FL from $153

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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 couple walking on a deck with lounge chairs and a railing overlooking the ocean.
A beachfront hotel with multiple balconies, a well-maintained lawn, and a clear view of the ocean.
A balcony with white railings, a view of the beach, and palm trees.

1. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
United States
Jacob Stuart
$239 nightly
$269 total
Oct 25 - Oct 26
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Pool
A couple holding hands in a tropical setting with palm trees and greenery.
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.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
$175 nightly
$197 total
Oct 25 - Oct 26
Total with taxes and fees
Blue Flamingo Resort Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A beach with clear blue water, a sandy shore, and a distant bridge.
A resort with a beach, a dock, and a water view.
A balcony with wicker furniture, a view of the ocean, and a building with balconies and palm trees.

3. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
William N
$350 nightly
$394 total
Nov 2 - Nov 3
Total with taxes and fees
Pier House Resort & Spa
A hotel with a swimming pool, balconies, and a view of the sea.
A balcony with a table and chairs, overlooking a turquoise sea with boats and a distant shoreline.
A parrot perched on a white ledge with a clear blue sky and distant landscape in the background.
A modern hotel room with a large sofa, a small table, and a bed. The room has large windows with a view of the sea and palm trees.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
Jennifer
$316 nightly
$356 total
Oct 19 - Oct 20
Total with taxes and fees
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 hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
A beach with a palm tree and two chairs.
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
Richard
$260 nightly
$293 total
Oct 30 - Oct 31
Total with taxes and fees
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.
The exterior of La Concha Key West hotel with a prominent entrance and a sign displaying the hotel's name.
A balcony with a hanging chair, a sofa, a TV, and a bookshelf.

6. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Key West Historic District
United States
THOMAS
$289 nightly
$325 total
Oct 25 - Oct 26
Total with taxes and fees
La Concha Key West, Autograph Collection
A swimming pool surrounded by palm trees and a natural rock formation.
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.
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
$200 nightly
$225 total
Nov 1 - Nov 2
Total with taxes and fees
Havana Cabana at Key West
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.
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
$149 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A large, white building with multiple arched windows and a central entrance, surrounded by palm trees and a pool.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A wooden pier leading to a turquoise sea under a clear sky.
A hotel room with a large bed, a desk, a chair, a TV, and a balcony with a view of greenery.

9. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
United States
Charlene
$276 nightly
$310 total
Oct 25 - Oct 26
Total with taxes and fees
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, 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
$203 nightly
$228 total
Oct 29 - Oct 30
Total with taxes and fees
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 restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

11. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
$204 nightly
$229 total
Oct 18 - Oct 19
Total with taxes and fees
The Perry Hotel & Marina Key West
A pool area with lounge chairs, umbrellas, and a two-story building with balconies.
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.
A wooden bench, a small table, and a white door in a garden with plants and a brick pathway.

12. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
United States
Elizabeth
$245 nightly
$276 total
Oct 18 - Oct 19
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
A hotel with a covered entrance, multiple balconies, and palm trees.
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.
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

13. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Susan
$294 nightly
$331 total
Oct 18 - Oct 19
Total with taxes and fees
Opal Key Resort & Marina, Key West
A marina with boats docked, a pool area, and a building with a white facade.
A waterfront hotel with a pool, palm trees, and a wooden dock.
A marina with numerous boats docked, a swimming pool, and palm trees.
A pool area with a view of a marina filled with boats, surrounded by palm trees and a white gazebo.

14. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Eric A
$174 nightly
$196 total
Oct 27 - Oct 28
Total with taxes and fees
Hilton Key West Resort & Marina
A pool area with lounge chairs and a cabana.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.
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
$371 nightly
$417 total
Oct 20 - Oct 21
Total with taxes and fees
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.
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
$212 nightly
$239 total
Oct 26 - Oct 27
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 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
$244 nightly
$275 total
Oct 25 - Oct 26
Total with taxes and fees
The Marker Key West Harbor Resort
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a white building.
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A covered porch with wooden flooring, potted plants, and outdoor furniture.
A cozy attic bedroom with a large bed, wooden ceiling, and a TV.

18. Eden House

Eden House
Key West Historic District
United States
Michelle
$136 nightly
$153 total
Oct 18 - Oct 19
Total with taxes and fees
Eden House
A glass-enclosed balcony with a pool, lounge chairs, and a table.
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 pool area with lounge chairs and palm trees.

19. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
$359 nightly
$404 total
Oct 26 - Oct 27
Total with taxes and fees
Santa Maria Suites
A swimming pool with lounge chairs and umbrellas, surrounded by lush greenery and a gazebo.
A white house with blue shutters, a front porch, and potted plants.
A brick pathway leading to a white building with large windows, surrounded by lush tropical vegetation.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building in the background.

20. The Gardens Hotel

The Gardens Hotel
Old Town Key West
United States
Gisele
$359 nightly
$404 total
Oct 26 - Oct 27
Total with taxes and fees
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 it’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 2 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 3 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

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.
  • Search for the lowest price from $153
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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