Lower Sugarloaf Key Vacation Rentals

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Our top choices for Lower Sugarloaf Key vacation rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (339 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is CA $160
CA $373 total
includes taxes & fees
May 27 - May 28
Old Wooden Bridge Resort and Marina

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is CA $553
CA $750 total
includes taxes & fees
Jun 2 - Jun 3
Ocean Front One Bedroom Residence

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $773
CA $1,411 total
includes taxes & fees
Jun 19 - Jun 20
Atlantic View Luxury Villa with Pool

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is CA $1,458
CA $2,190 total
includes taxes & fees
Jun 14 - Jun 15
Contra House Key West

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is CA $804
CA $1,761 total
includes taxes & fees
May 26 - May 27
Lighthouse Suites Collection

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (186 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is CA $184
CA $438 total
includes taxes & fees
May 27 - May 28
Aqua Lodges at Hurricane Hole Marina

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is CA $568
CA $1,141 total
includes taxes & fees
May 24 - May 25
Starlight Serenity - Hideaway w Stunning Views

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is CA $1,275
CA $2,894 total
includes taxes & fees
Jun 21 - Jun 22
Waterfront Luxury Home - Tidelands House

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is CA $1,396
CA $3,031 total
includes taxes & fees
Jun 21 - Jun 22
The Fairhaven House at Solaire Lunara Bay

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,426 total
includes taxes & fees
May 28 - May 29
Waterlane House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,426 total
includes taxes & fees
Jun 7 - Jun 8
Aquaria House by Brightwild Pool Boat Dock

Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,672 total
includes taxes & fees
May 28 - May 29
Mirador House by Brightwild Pool Dock

Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,672 total
includes taxes & fees
May 27 - May 28
Suncoast House by Brightwild Pool Boat Dock

Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,426 total
includes taxes & fees
Jun 8 - Jun 9
Springtide House by Brightwild Waterfront Pool

Floralee House in Key West

Floralee House in Key West
2.0 star property
Raccoon Key
The price is CA $1,264
CA $2,791 total
includes taxes & fees
May 25 - May 26
Floralee House in Key West

Palmgale House in Key West

Palmgale House in Key West
2.0 star property
Raccoon Key
The price is CA $1,047
CA $2,546 total
includes taxes & fees
Jun 8 - Jun 9
Palmgale House in Key West

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is CA $967
CA $2,091 total
includes taxes & fees
Jun 3 - Jun 4
Capmar House by Brightwild Huge Home Pool

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is CA $359
CA $814 total
includes taxes & fees
May 25 - May 26
Tortuga Suite Sparkling Pool Hot Tub

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
Poolside Suite by Brightwild Pvt Pool Parking

Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos
2.0 star property
Old Town Key West
The price is CA $1,839
CA $2,936 total
includes taxes & fees
Jun 3 - Jun 4
Sky Suites Retreat by Brightwild 2 Stunning Condos
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 Lower Sugarloaf Key Hotel Reviews

Find out more about Lower Sugarloaf Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lower Sugarloaf Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.