A waterfront with a pier, calm water, and houses with palm trees in the background.

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, (349 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is CA $169
CA $390 total
includes taxes & fees
Jul 9 - Jul 10
Old Wooden Bridge Resort and 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, (190 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 $154
CA $412 total
includes taxes & fees
Jul 5 - Jul 6
Aqua Lodges at Hurricane Hole Marina

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 host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is CA $446
CA $1,003 total
includes taxes & fees
Jul 7 - Jul 8
Starlight Serenity - Hideaway w Stunning Views

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 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 $926
CA $1,601 total
includes taxes & fees
Jul 31 - Aug 1
Atlantic View Luxury Villa with Pool

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is CA $649
CA $1,615 total
includes taxes & fees
Jul 12 - Jul 13
Lighthouse Suites Collection

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is CA $1,309
CA $2,041 total
includes taxes & fees
Jul 7 - Jul 8
Contra House Key West

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is CA $1,404
CA $1,864 total
includes taxes & fees
Jul 12 - Jul 13
Coconut Mallory Marina and Resort Condo

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is CA $383
CA $776 total
includes taxes & fees
Jul 6 - Jul 7
Grand Marina Suite by Brightwild Waterfront

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is CA $471
CA $653 total
includes taxes & fees
Jul 13 - Jul 14
Ocean Front One Bedroom Residence

New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
The price is CA $414
CA $712 total
includes taxes & fees
Jul 5 - Jul 6
New Rose Petal Petite Suite - Pool Parking

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is CA $352
CA $524 total
includes taxes & fees
Jul 7 - Jul 8
Island View 1BR Residence With Balcony

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is CA $255
CA $697 total
includes taxes & fees
Jul 5 - Jul 6
The Grenada Suite Pool View Private Balcony

New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2 reviews)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is CA $284
CA $501 total
includes taxes & fees
Jul 6 - Jul 7
New The Cottage at James House

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is CA $311
CA $623 total
includes taxes & fees
Jul 6 - Jul 7
The Bartlum Luxury Studio In Prime Location

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is CA $386
CA $844 total
includes taxes & fees
Jul 5 - Jul 6
Tortuga Suite Sparkling Pool Hot Tub

Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is CA $246
CA $578 total
includes taxes & fees
Jul 7 - Jul 8
Banana Split by Brightwild Pool Grill

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 $1,272
CA $2,432 total
includes taxes & fees
Jul 19 - Jul 20
Capmar House by Brightwild Huge Home Pool

Poolside Retreat by Brightwild Cottage w Pool

Poolside Retreat by Brightwild Cottage w Pool
2.5 star property
Old Town Key West
2.0 out of 10, (1 review)
"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...
United States
Julia
The price is CA $310
CA $622 total
includes taxes & fees
Jul 13 - Jul 14
Poolside Retreat by Brightwild Cottage w Pool

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is CA $373
CA $547 total
includes taxes & fees
Jul 7 - Jul 8
Resort View 1BR Suite With Direct Pool Access

Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is CA $1,280
CA $2,441 total
includes taxes & fees
Jul 7 - Jul 8
Seagate House by Brightwild Waterfront w Dock
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.

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