Find hotels in Sugarloaf Key, FL from ₩164,054

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Dec 13 - Dec 14
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Our top choices for Sugarloaf Key hotels

Restaurant
Sugar Loaf Lodge

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1002)
"Great place to stary. Staff was very nice."
United States
norka
The price is ₩145,819
₩164,054 total
includes taxes & fees
Dec 19 - Dec 20
Sugar Loaf Lodge
House | 2 bedrooms, Internet
Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is ₩401,359
₩945,269 total
includes taxes & fees
Dec 15 - Dec 16
Starlight Serenity - Hideaway w Stunning Views
Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view
Parmer's Resort

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1001)
"Room was clean and comfortable."
United States
Barbara K
The price is ₩198,161
₩271,150 total
includes taxes & fees
Dec 14 - Dec 15
Parmer's Resort
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town
8.0 out of 10, Very Good, (1151)
Tucked within a 10-minute drive of Duval Street and Smathers Beach, this hotel offers a refreshing outdoor pool and relaxing hot tub. Enjoy American cuisine at The Garden Grille, unwind at the poolside bar, and utilize the convenient free area shuttle to explore vibrant Key West.
" Dry friendly and good breakfast and excellent value for money "
United States
Meenakshi
The price is ₩174,806
₩238,090 total
includes taxes & fees
Dec 18 - Dec 19
Hilton Garden Inn Key West / The Keys Collection
Front of property - evening/night
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1020)
Steps from Mallory Square in Key West, this resort offers a refreshing outdoor pool with poolside bar. Unwind with a massage or explore the full-service marina. The 3 bars and on-site restaurant keep you fueled between adventures on nearby Duval Street.
"Our stay was great!"
United States
Richard
The price is ₩410,945
₩520,324 total
includes taxes & fees
Dec 14 - Dec 15
Opal Key Resort & Marina, Key West
Exterior
Looe Key Reef Resort

Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.4 out of 10, Good, (1001)
"Was nice roo.s and close to my charter boat captain "
United States
Nicholas
Looe Key Reef Resort
Garden
Douglas House

Douglas House

Douglas House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (223)
Unwind in this tranquil guesthouse just steps from Florida Keys Beaches and Duval Street. The outdoor pool provides a refreshing escape after exploring nearby Ernest Hemingway Home. Free WiFi and parking enhance your Key West adventure.
"We were very pleased with everything and great location."
United States
Lynn
The price is ₩202,344
₩250,401 total
includes taxes & fees
Dec 15 - Dec 16
Douglas House
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
Key West
8.0 out of 10, Very Good, (1001)
"Very very nice stay! "
United States
Chloe
The price is ₩215,459
₩292,102 total
includes taxes & fees
Dec 18 - Dec 19
DoubleTree Resort by Hilton Grand Key - Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1172)
This waterfront haven boasts 2 seafood restaurants, 2 poolside bars, and a 24-hour fitness center. Just a short drive from Smathers Beach and Duval Street, the hotel's marina setting offers a peaceful atmosphere with easy access to Key West's popular attractions.
"great place to stay "
United States
michael
The price is ₩383,265
₩521,920 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Perry Hotel & Marina Key West
Outdoor pool
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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
8.6 out of 10, Excellent, (1006)
Embrace the tranquil atmosphere of this Key West hotel featuring a refreshing outdoor pool with poolside bar. Just minutes from Duval Street and Smathers Beach, guests enjoy convenient room service, free breakfast, and thoughtful courtyard spaces.
"Staff is friendly and knowledgeable in local attractions."
United States
Sheng
The price is ₩226,830
₩296,603 total
includes taxes & fees
Dec 18 - Dec 19
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
4 outdoor pools, pool umbrellas, sun loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
4.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1189)
Waterfront paradise featuring easy access to onsite kayaking and 4 pristine pools. The Grove Kitchen and Bar offers poolside dining, while a fitness center and beach shuttle add convenience. Just minutes from Duval Street and Smathers Beach.
"Great hotel"
United States
Patrice
The price is ₩300,197
₩422,513 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Parrot Key Hotel & Villas
View from property
Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
3.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1001)
Experience Key West charm at this waterfront hotel just minutes from Duval Street. The outdoor pool, hot tub, and poolside bar create a relaxing retreat. Enjoy garden views, a coffee shop, and complimentary WiFi while staying near Florida Keys Beaches.
"Room clean, nice pool area"
United States
Tami
The price is ₩204,736
₩230,328 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Key West Waterfront
Outdoor pool, sun loungers
Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
New Town
8.8 out of 10, Excellent, (1726)
Dive into Key West charm at this hotel with the largest pool on the island. Cuban flavors await at Floridita Food Truck, while the poolside bar and hot tub elevate relaxation. Convenient access to Duval Street and Smathers Beach completes your Florida getaway.
"Pretty much everything you could hope for out of a resort. Staff was great, amenities were nice, the room was clean. We loved out stay"
United States
alec lawrence
The price is ₩438,596
₩597,037 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Havana Cabana at Key West
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1073)
Wake to a complimentary breakfast at this charming Key West hotel featuring 3 sparkling outdoor pools and a poolside bar. Just a 10-minute stroll from Duval Street's excitement and Hemingway's former residence, guests love the convenient location and attentive staff.
"Beautiful property, nice clean bungalows and great staff!"
United States
Robert
The price is ₩337,878
₩454,929 total
includes taxes & fees
Dec 16 - Dec 17
Winslow's Bungalows - Key West Historic Inns
Outdoor spa tub
NYAH Key West - Adults Only

NYAH Key West - Adults Only

NYAH Key West - Adults Only
3.0 star property
Key West Historic District
8.0 out of 10, Very Good, (1002)
This adults-only guesthouse offers free breakfast and a rooftop terrace just a short walk from Duval Street. After exploring nearby Ernest Hemingway Home, unwind in the hot tub or grab a drink at the bar. Guests love the 3 outdoor pools and attentive staff.
"Great little hotel in the heart of Old Town."
United States
Robert
NYAH Key West - Adults Only
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas
The Laureate Key West

The Laureate Key West

The Laureate Key West
3.5 star property
New Town
9.0 out of 10, Wonderful, (1003)
Waterfront elegance meets Key West charm at this coastal retreat. Just minutes from Duval Street and Smathers Beach, the hotel offers a refreshing indoor pool and 24-hour service. Nearby adventures include kayaking and snorkeling, with Hemingway's home a short drive away.
"Nice place to stay!"
Canada
Baohua
The price is ₩263,653
₩338,050 total
includes taxes & fees
Dec 14 - Dec 15
The Laureate Key West
Boating
Ibis Bay Beach Resort

Ibis Bay Beach Resort

Ibis Bay Beach Resort
2.5 star property
Northside Resort
8.2 out of 10, Very Good, (2009)
"Pool was nice & property was clean and appealing "
United States
Selene
The price is ₩171,394
₩232,540 total
includes taxes & fees
Dec 14 - Dec 15
Ibis Bay Beach Resort
View from property
Duval House

Duval House

Duval House
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1006)
Immerse yourself in Key West's vibrant atmosphere at this B&B with a refreshing pool and lush garden. Just minutes from Duval Street and Hemingway's Museum, enjoy daily housekeeping and a delicious breakfast while adventure awaits with nearby hiking, kayaking, and diving.
"I loved this place the location was absolutely perfect "
United States
Frank
The price is ₩199,491
₩256,199 total
includes taxes & fees
Dec 15 - Dec 16
Duval House
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (846)
This tranquil retreat offers beautiful gardens and a refreshing pool with bar. Just steps from Duval Street and Hemingway's former residence, guests praise the peaceful atmosphere and helpful staff. Enjoy free breakfast while exploring the island.
"Great location. Near great food and entertainment."
United States
David
The price is ₩357,555
₩477,066 total
includes taxes & fees
Dec 15 - Dec 16
Lighthouse Hotel - Key West Historic Inns
Fountain
Colors on White

Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very Good, (380)
This charming guesthouse offers an outdoor pool and is just a 15-minute walk from Duval Street and Hemingway Museum. Florida Keys Beaches and Southernmost Point are a quick 5-minute drive away. Enjoy free WiFi and parking during your stay.
"Very nice place to be at. Close walking and biking distance "
United States
brad
Colors on White
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.
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Stay near popular South Florida attractions

Sugarloaf Beach

3.6/5 (7 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

Upper Sugarloaf Key

4.1/5 (37 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
See properties

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
Sugarloaf Shores which includes a bay or harbor and a house

Top Sugarloaf Key Hotel Reviews

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Beautiful place"
Charlene 2-night trip
Posted 2 days ago
Hyatt Vacation Club at Beach House, Key West

More cheap stays in Sugarloaf Key

Sugar Loaf Lodge

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL
The price is ₩145,819 per night from Dec 19 to Dec 20
₩145,819
₩164,054 total
Dec 19 - Dec 20
includes taxes & fees
8/10 Very Good! (1,001 reviews)

Hotels in Sugarloaf Key with star-rating

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