Hotels in Sugarloaf Key

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Where to stay in Sugarloaf Key?

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,000 reviews)
The price is $99
$111 total
includes taxes & fees
Nov 30 - Dec 1
Sugar Loaf Lodge

2. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
The price is $345
$735 total
includes taxes & fees
Nov 19 - Nov 20
Starlight Serenity - Hideaway w Stunning Views

3. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.8 out of 10, Good, (1,000 reviews)
The price is $145
$163 total
includes taxes & fees
Nov 9 - Nov 10
Looe Key Reef Resort

4. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1,314 reviews)
Escape to this waterfront retreat with a marina, where 2 outdoor pools and poolside bars await. Feast on seafood at Matt's Stock Island, then explore nearby Duval Street and Smathers Beach. A 24-hour fitness center and free WiFi complete your Key West getaway.
The price is $131
$205 total
includes taxes & fees
Nov 30 - Dec 1
The Perry Hotel & Marina Key West

5. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
4.0 star property
Stock Island
9.0 out of 10, Wonderful, (1,791 reviews)
Dive into a tropical oasis at this Key West resort featuring a marina, poolside bar, and complimentary bicycles. Just minutes from Smathers Beach and Duval Street, guests love the 24-hour fitness center and helpful staff.
The price is $126
$201 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Key West Resort & Marina

6. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,001 reviews)
The price is $169
$223 total
includes taxes & fees
Nov 18 - Nov 19
Parmer's Resort

7. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
New Town
8.8 out of 10, Excellent, (1,179 reviews)
The price is $125
$169 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town
8.2 out of 10, Very good, (1,353 reviews)
This garden hotel offers a relaxing escape with outdoor pool, jacuzzi, and poolside bar. Just minutes from Key West Airport with a free area shuttle to nearby attractions including Duval Street and Smathers Beach.
The price is $115
$158 total
includes taxes & fees
Nov 17 - Nov 18
Hilton Garden Inn Key West / The Keys Collection

9. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
Key West
8.4 out of 10, Very good, (1,131 reviews)
The price is $123
$172 total
includes taxes & fees
Nov 15 - Nov 16
DoubleTree Resort by Hilton Grand Key - Key West

10. Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1,569 reviews)
Experience oceanfront bliss at this peaceful retreat with stunning sunset views. Just a 5-minute drive from Smathers Beach and Florida Keys Beaches, enjoy the outdoor pool, poolside bar, and complimentary breakfast before exploring nearby Duval Street with the convenient shuttle service.
The price is $188
$212 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn Key West FL

11. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (380 reviews)
Feel the coastal breeze at this Big Pine Key marina resort where adventure awaits. Hike scenic trails, kayak crystal waters, or lounge by the pool. Near Blue Hole and Bahia Honda State Park, with rooms featuring microwaves and free WiFi.
The price is $129
$286 total
includes taxes & fees
Nov 5 - Nov 6
Old Wooden Bridge Resort and Marina

12. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,335 reviews)
Enjoy incredible views of the Atlantic from this Key West hotel with spacious accommodations featuring washers/dryers and refrigerators. The outdoor pool, hot tub, and snack bar create a relaxing atmosphere near Duval Street with free WiFi and parking.
The price is $160
$225 total
includes taxes & fees
Nov 17 - Nov 18
Hyatt Vacation Club at Windward Pointe, Key West

13. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.6 out of 10, Excellent, (2,767 reviews)
Immerse in tropical living at this family-friendly resort near Duval Street and Smathers Beach. Enjoy 2 restaurants including the Toasted Coconut serving American cuisine, plus 2 poolside bars, a hot tub, and 24-hour fitness center, all with free WiFi.
The price is $134
$207 total
includes taxes & fees
Nov 15 - Nov 16
Blue Flamingo Resort Key West

14. The Laureate Key West

The Laureate Key West
3.5 star property
New Town
9.2 out of 10, Wonderful, (1,037 reviews)
Immerse yourself in Key West charm at this beachside retreat with an indoor pool. Located near iconic spots like Southernmost Point and Smathers Beach, the hotel offers easy access to kayaking, scuba diving, and snorkeling adventures with 24-hour service.
The price is $159
$207 total
includes taxes & fees
Nov 10 - Nov 11
The Laureate Key West

15. Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
New Town
9.0 out of 10, Wonderful, (1,905 reviews)
Key West's coastal hideaway features the island's largest pool, complete with hot tub and poolside bar. Cuban flavors await at Floridita Food Truck, while Duval Street and beaches are just minutes away. In-room refrigerators and microwaves enhance your tropical getaway.
The price is $136
$216 total
includes taxes & fees
Dec 3 - Dec 4
Havana Cabana at Key West

16. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
4.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1,483 reviews)
Escape to this beachfront haven with 4 sparkling pools and onsite kayaking. The Grove Kitchen serves meals by the water, while a fitness center keeps you active. Just minutes from Duval Street and Smathers Beach, with easy airport access.
The price is $149
$225 total
includes taxes & fees
Nov 15 - Nov 16
Parrot Key Hotel & Villas

17. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.4 out of 10, Very good, (1,007 reviews)
Escape to a private beachfront sanctuary in the Florida Keys, where 2 sparkling pools meet pristine shoreline. Savor magical sunsets after a spa massage, then stroll to nearby Duval Street and South Beach attractions.
The price is $256
$356 total
includes taxes & fees
Nov 23 - Nov 24
Casa Marina Key West, Curio Collection by Hilton

18. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
3.0 star property
Northside Resort
8.8 out of 10, Excellent, (1,004 reviews)
Relax in beach-side sun loungers just 5 minutes from Florida Keys Beaches. This waterfront hotel offers an outdoor pool with hot tub, poolside bar, and garden. Nearby Duval Street and Smathers Beach provide local flair, plus free WiFi and parking.
The price is $178
$201 total
includes taxes & fees
Nov 16 - Nov 17
Courtyard by Marriott Key West Waterfront

19. Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,286 reviews)
Set along the Florida Keys shoreline, this peaceful hotel offers easy access to Duval Street and Smathers Beach. Enjoy complimentary WiFi and parking while unwinding in the hot tub after exploring nearby Ernest Hemingway's Home.
The price is $230
$304 total
includes taxes & fees
Nov 28 - Nov 29
Hyatt Vacation Club at Beach House, Key West

20. Southwinds Motel

Southwinds Motel
2.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1,395 reviews)
Tucked between South Beach and Southernmost Point, this Key West gem offers 2 refreshing outdoor pools and complimentary breakfast. Travelers consistently praise the comfortable beds, helpful staff, and prime location for exploring the island's vibrant attractions.
The price is $154
$207 total
includes taxes & fees
Dec 1 - Dec 2
Southwinds Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Go beyond your typical stay in Sugarloaf Key

Learn more about Sugarloaf Key

Between mangrove tunnels and crystal waters, this Florida Keys paradise offers adventures without the Key West crowds. Kayak through natural channels where great blue herons stand sentinel and manatees might glide beneath your paddle. The underwater wonderland of Looe Key National Marine Sanctuary beckons with its kaleidoscope of coral and tropical fish just offshore. Sugarloaf Beach provides a quiet alternative to busier shores, while local bars serve conch fritters and key lime cocktails with zero pretension. For a perfect day, paddle Upper Sugarloaf Sound in the morning, snorkel after lunch, then claim a spot at a waterfront bar where locals swap fishing tales as the sun melts into the Gulf.

A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

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Frequently Asked Questions

Why should I book my Sugarloaf Key hotel with Hotels.com?

There are lots of reasons to book your Sugarloaf Key trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.