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Our top choices for Sugarloaf Key holiday rentals

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is £675
includes taxes & fees
14 May - 15 May
Starlight Serenity - Hideaway w Stunning Views

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is £430
includes taxes & fees
11 May - 12 May
Ocean Front One Bedroom Residence

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (332 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
The price is £200
includes taxes & fees
21 May - 22 May
Old Wooden Bridge Resort and Marina

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is £978
includes taxes & fees
4 May - 5 May
Contra House Key West

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is £905
includes taxes & fees
5 May - 6 May
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, (183 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 £227
includes taxes & fees
10 May - 11 May
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 £756
includes taxes & fees
8 May - 9 May
Atlantic View Luxury Villa with 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 £358
includes taxes & fees
11 May - 12 May
Resort View 1BR Suite With Direct Pool Access

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 £475
includes taxes & fees
7 May - 8 May
Poolside Suite by Brightwild Pvt Pool Parking

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 £556
includes taxes & fees
11 May - 12 May
Sea Breeze by Brightwild Off-street Parking

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is £364
includes taxes & fees
6 May - 7 May
Mesa House Uno by Brightwild Perfect Location

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
New Rose Retreat - Pool 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
The price is £730
includes taxes & fees
5 May - 6 May
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
The price is £472
includes taxes & fees
3 Jun - 4 Jun
New Coastal Rose - Bright Loft With High Ceilings

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is £436
includes taxes & fees
19 May - 20 May
Tortuga Suite Sparkling Pool Hot Tub

Kamp by Brightwild Rooftop Penthouse On Duval

Kamp by Brightwild Rooftop Penthouse On Duval
2.0 star property
Old Town Key West
The price is £839
includes taxes & fees
5 May - 6 May
Kamp by Brightwild Rooftop Penthouse On Duval

Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is £913
includes taxes & fees
17 May - 18 May
Commodore s Cove by Brightwild Epic Location

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is £874
includes taxes & fees
11 May - 12 May
Resort View 3BR Residence

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is £740
includes taxes & fees
11 May - 12 May
Ocean Front 2BR Residence

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is £754
includes taxes & fees
27 May - 28 May
Duval Dream Loft by Brightwild Right on Duval
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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Find out more about Sugarloaf Key

Everything you need to know about Sugarloaf Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sugarloaf Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugarloaf Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugarloaf Key holiday rentals we have selected for you start as low as £200 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key holiday 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 holiday.

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.