Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation rentals

Vacation Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
$2,063 nightly
The price is $2,284
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Hemingway - Beach Houses Key West

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
$704 nightly
The price is $792
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
$631 nightly
The price is $702
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
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.
$1,579 nightly
The price is $1,763
Dec 28 - Dec 29
Total with taxes and fees
The Lighthouse - Beach Houses Key West

Vacation Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
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.
$1,824 nightly
The price is $2,005
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palm - Beach Houses Key West

Vacation Home in Sugarloaf Key

Hammock House - Beach Houses Key West
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.
$1,990 nightly
The price is $2,189
Dec 27 - Dec 28
Total with taxes and fees
Hammock House - Beach Houses Key West

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
$355 nightly
The price is $400
Jan 5 - Jan 6, 2026
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
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
$454 nightly
The price is $504
Jan 4 - Jan 5, 2026
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
2.5 star property
8.6 out of 10, Excellent, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
$241 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
Old Wooden Bridge Resort and Marina
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!
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.
$341 nightly
The price is $379
Jan 19 - Jan 20, 2026
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$548 nightly
The price is $610
Jan 10 - Jan 11, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
3.5 star property
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
$975 nightly
The price is $1,097
Jan 16 - Jan 17, 2026
Total with taxes and fees
Atlantic View Luxury Villa with Pool
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.
$548 nightly
The price is $610
Jan 18 - Jan 19, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
$749 nightly
The price is $831
Jan 1 - Jan 2, 2026
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
$1,186 nightly
The price is $1,316
Jan 7 - Jan 8, 2026
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
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 traveler
$1,427 nightly
The price is $1,583
Jan 5 - Jan 6, 2026
Total with taxes and fees
Capmar House at Lunara Bay

Vacation Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
$1,376 nightly
The price is $1,532
Jan 4 - Jan 5, 2026
Total with taxes and fees
Springtide House at Lunara Bay

Vacation Home in Raccoon Key

Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
$2,226 nightly
The price is $2,470
Jan 4 - Jan 5, 2026
Total with taxes and fees
Larkshine House at Lunara Bay

Vacation Home in Raccoon Key

Floralee House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (8)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
$1,884 nightly
The price is $2,090
Jan 4 - Jan 5, 2026
Total with taxes and fees
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

Find out more about Sugarloaf Key

Everything you need to know about Sugarloaf Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sugarloaf Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sugarloaf Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sugarloaf Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sugarloaf Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $271 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sugarloaf Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sugarloaf Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sugarloaf Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.