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

Find 4 Star Hotels in Sugarloaf Key, FL from $168

Check availability on Sugarloaf Key 4 Star Hotels

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Oct 17 - Oct 18
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Oct 18 - Oct 19
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Oct 23 - Oct 25
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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 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.

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 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.

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 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 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
$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 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 balcony with a view of the ocean, a table, chairs, and a railing.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
Joseph
$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 person standing by a window overlooking a beach with palm trees and 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.

5. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
Siamak
$264 nightly
$297 total
Oct 31 - Nov 1
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 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.
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.

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 covered outdoor seating area with a pool in the background.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

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 sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

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 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 spacious lobby with green sofas, a coffee table, and a dining area.

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 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.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

10. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
$192 nightly
$216 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 marina with boats docked, a swimming pool, and palm trees.

11. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
$167 nightly
$187 total
Nov 2 - Nov 3
Total with taxes and fees
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 picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.
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
$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 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
$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 covered outdoor seating area with tables and chairs, overlooking a marina with boats.
A clear view of turquoise ocean water and a blue sky with clouds.
A marina with numerous boats docked, a swimming pool, and palm trees.

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 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 balcony with a table set for breakfast, overlooking the sea.

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 18 - Oct 19
Total with taxes and fees
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.
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.

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 covered outdoor area with a pool, palm trees, and lounge chairs.

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 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 cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
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
$159 nightly
$179 total
Oct 28 - Oct 29
Total with taxes and fees
Eden House
A pool area with lounge chairs and palm trees.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.
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
$359 nightly
$404 total
Oct 26 - Oct 27
Total with taxes and fees
Santa Maria Suites
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A couple walking along a poolside pathway surrounded by lush greenery.
A bar area with a counter, chairs, and a clock.

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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"👍"
Peter 1-night trip
Posted 1 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 5 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 6 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 11 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 12 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

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 $168
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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