Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation rentals

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is CA $699
CA $1,256 total
includes taxes & fees
Jun 17 - Jun 18
Starlight Serenity - Hideaway w Stunning Views

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (342 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is CA $185
CA $402 total
includes taxes & fees
Jun 8 - Jun 9
Old Wooden Bridge Resort and Marina

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 $379
CA $546 total
includes taxes & fees
Jun 2 - Jun 3
Resort View 1BR Suite With Direct Pool Access

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is CA $644
CA $1,584 total
includes taxes & fees
Jun 2 - Jun 3
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, (187 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 $168
CA $420 total
includes taxes & fees
Jun 7 - Jun 8
Aqua Lodges at Hurricane Hole Marina

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 $776
CA $1,416 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
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is CA $1,301
CA $2,015 total
includes taxes & fees
Jun 7 - Jun 8
Contra House Key West

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is CA $467
CA $645 total
includes taxes & fees
Jun 2 - Jun 3
Ocean Front One Bedroom Residence

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
The price is CA $271
CA $731 total
includes taxes & fees
Jun 3 - Jun 4
New Coastal Rose - Bright Loft With High Ceilings

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is CA $416
CA $852 total
includes taxes & fees
Jun 9 - Jun 10
Poolside Suite by Brightwild Pvt Pool Parking

Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is CA $270
CA $585 total
includes taxes & fees
Jun 8 - Jun 9
Banana Split by Brightwild Pool Grill

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 $410
CA $803 total
includes taxes & fees
Jun 2 - Jun 3
Grand Marina Suite by Brightwild Waterfront

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 $358
CA $523 total
includes taxes & fees
Jun 2 - Jun 3
Island View 1BR Residence With Balcony

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is CA $359
CA $788 total
includes taxes & fees
Jun 7 - Jun 8
Tortuga Suite Sparkling Pool Hot Tub

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 $286
CA $705 total
includes taxes & fees
Jun 28 - Jun 29
The Grenada Suite Pool View Private Balcony

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is CA $550
CA $909 total
includes taxes & fees
Jun 2 - Jun 3
Resort View 2BR Residence

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is CA $651
CA $1,100 total
includes taxes & fees
Jun 2 - Jun 3
Ocean Front 2BR Residence

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is CA $541
CA $1,061 total
includes taxes & fees
Jun 2 - Jun 3
Sea Breeze by Brightwild Off-street Parking

The Collins on Duval by Brightwild

The Collins on Duval by Brightwild
2.0 star property
Old Town Key West
The price is CA $634
CA $1,183 total
includes taxes & fees
Jun 2 - Jun 3
The Collins on Duval by Brightwild

Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
The price is CA $547
CA $1,085 total
includes taxes & fees
Jun 2 - Jun 3
Sky Suite on Duval by Brightwild Condo w Balcony
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

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 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.