Sugarloaf Key Holiday Rentals

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Sugarloaf Key holiday rentals

Pool
The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is HK$10,692
HK$17,759 total
includes taxes & fees
3 Jan - 4 Jan 2026
The Hemingway - Beach Houses Key West
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 HK$3,150
HK$6,142 total
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway w Stunning Views
Fridge, microwave, oven, stovetop
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is HK$2,232
HK$5,430 total
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway with Stunning Views
Pool
The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is HK$8,553
HK$13,711 total
includes taxes & fees
28 Dec - 29 Dec
The Lighthouse - Beach Houses Key West
Pool
Palm - Beach Houses Key West

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is HK$8,511
HK$15,589 total
includes taxes & fees
4 Jan - 5 Jan 2026
Palm - Beach Houses Key West
Pool
Hammock House - Beach Houses Key West

Hammock House - Beach Houses Key West

Hammock House - Beach Houses Key West
Sugarloaf Key
8.0 out of 10, Very good, (2)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is HK$9,366
HK$17,020 total
includes taxes & fees
27 Dec - 28 Dec
Hammock House - Beach Houses Key West
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is HK$1,523
HK$3,016 total
includes taxes & fees
3 Jan - 4 Jan 2026
Aqua Lodges at Hurricane Hole Marina
Outdoor pool
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$1,944
HK$3,919 total
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Living area
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (283)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina
Miscellaneous
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, just minutes to Key West!
Beach
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is HK$1,750
HK$2,943 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor dining
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Swim-up bar
Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$4,374
HK$7,982 total
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool
Outdoor pool, a heated pool
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is HK$3,149
HK$6,461 total
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is HK$4,192
HK$10,232 total
includes taxes & fees
7 Jan - 8 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.
Pool
Capmar House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is HK$5,435
HK$12,310 total
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is HK$5,435
HK$11,914 total
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay
Outdoor dining
Larkshine House at Lunara Bay

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is HK$9,323
HK$19,203 total
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
Pool
Floralee House at Lunara Bay

Floralee House at Lunara Bay

Floralee House at Lunara Bay
2.0 star property
Raccoon Key
9.8 out of 10, Exceptional, (8)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
The price is HK$6,990
HK$16,252 total
includes taxes & fees
4 Jan - 5 Jan 2026
Floralee House at Lunara Bay
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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Top Sugarloaf Key Hotel Reviews

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"Staff was all wonderful! Resort was the perfect size.. pool and bar area were perfect! Definitely recommend and will be going back! "
Kellie 4-night trip
Posted 3 days ago
Havana Cabana at Key West

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