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
$637 nightly
The price is $717
Jul 7 - Jul 8
Total with taxes and fees
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, (349 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
$220 nightly
The price is $248
Jun 28 - Jun 29
Total with taxes and fees
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
$352 nightly
The price is $396
Jul 6 - Jul 7
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
$1,028 nightly
The price is $1,149
Jun 27 - Jun 28
Total with taxes and fees
Lighthouse Suites Collection

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
$1,249 nightly
The price is $1,405
Jul 25 - Jul 26
Total with taxes and fees
Coconut Mallory Marina and Resort Condo

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
$248 nightly
The price is $279
Jun 30 - Jul 1
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

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
$1,181 nightly
The price is $1,328
Jun 29 - Jun 30
Total with taxes and fees
Contra House Key West

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
$531 nightly
The price is $597
Jun 28 - Jun 29
Total with taxes and fees
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

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
$1,075 nightly
The price is $1,209
Jul 27 - Jul 28
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$375 nightly
The price is $422
Jul 7 - Jul 8
Total with taxes and fees
Ocean Front One Bedroom Residence

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
$561 nightly
The price is $631
Jul 6 - Jul 7
Total with taxes and fees
Poolside Suite by Brightwild Pvt Pool Parking

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
$407 nightly
The price is $458
Jun 28 - Jun 29
Total with taxes and fees
Ocean Front 2BR Residence

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
$546 nightly
The price is $614
Jul 1 - Jul 2
Total with taxes and fees
Resort View 2BR Residence

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
$722 nightly
The price is $813
Jul 8 - Jul 9
Total with taxes and fees
Sea Breeze by Brightwild Off-street Parking

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
$707 nightly
The price is $796
Jul 13 - Jul 14
Total with taxes and fees
Sky Suite on Duval by Brightwild Condo w Balcony

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
$607 nightly
The price is $683
Jul 7 - Jul 8
Total with taxes and fees
New Coastal Rose - Bright Loft With High Ceilings

The Collins on Duval by Brightwild

The Collins on Duval by Brightwild
2.0 star property
Old Town Key West
$767 nightly
The price is $863
Jun 29 - Jun 30
Total with taxes and fees
The Collins on Duval by Brightwild

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
$830 nightly
The price is $934
Jun 28 - Jun 29
Total with taxes and fees
Resort View 3BR Residence

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
$990 nightly
The price is $1,114
Jul 8 - Jul 9
Total with taxes and fees
New Rose Retreat - Pool Parking

NEW The Rigby House - Pvt Pool Amazing Location

NEW The Rigby House - Pvt Pool Amazing Location
2.0 star property
Key West Historic District
$2,184 nightly
The price is $2,457
Jun 30 - Jul 1
Total with taxes and fees
NEW The Rigby House - Pvt Pool Amazing Location
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 $248 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.

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