Sugarloaf Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sugarloaf Key holiday rentals

2.0 star property
The price is NZ$1,342
includes taxes & fees
22 Jan - 23 Jan
Starlight Serenity - Hideaway w Stunning Views

Holiday Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is NZ$3,475
includes taxes & fees
17 Feb - 18 Feb
The Hemingway - Beach Houses Key West

Holiday Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The Lighthouse - Beach Houses Key West

Holiday Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
Private and Exclusive Florida Keys Getaway

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (173 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$530
includes taxes & fees
25 Jan - 26 Jan
Aqua Lodges at Hurricane Hole Marina
7.8 out of 10, Good, (26 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is NZ$870
includes taxes & fees
9 Feb - 10 Feb
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
The price is NZ$1,618
includes taxes & fees
15 Feb - 16 Feb
Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina
2.5 star property
8.6 out of 10, Excellent, (291 reviews)
"Everything was great"
United States
Isabella
Old Wooden Bridge Resort and Marina
9.0 out of 10, Wonderful, (162 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is NZ$598
includes taxes & fees
14 Feb - 15 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
8.6 out of 10, Excellent, (76 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
The price is NZ$789
includes taxes & fees
6 Feb - 7 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
The price is NZ$529
includes taxes & fees
22 Jan - 23 Jan
Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is NZ$653
includes taxes & fees
8 Feb - 9 Feb
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is NZ$720
includes taxes & fees
29 Jan - 30 Jan
Waterfront Home
3.5 star property
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
Atlantic View Luxury Villa with Pool
9.0 out of 10, Wonderful, (91 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is NZ$845
includes taxes & fees
1 Feb - 2 Feb
Canal front, dockage, 2 bedroom, 2 bath
2.5 star property
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is NZ$1,034
includes taxes & fees
3 Feb - 4 Feb
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Apartment in Long Beach Estates

Star Room Barnacle Resort
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
The price is NZ$613
includes taxes & fees
22 Jan - 23 Jan
Star Room Barnacle Resort
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is NZ$729
includes taxes & fees
26 Jan - 27 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (54 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is NZ$784
includes taxes & fees
2 Feb - 3 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (158 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

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, 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 NZ$529 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.