Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Holiday Home in Summerland Key

2.0 star property
The price is AU$934
includes taxes & fees
2 Dec - 3 Dec
Starlight Serenity - Hideaway w Stunning Views

Holiday Home in Summerland Key

The price is AU$954
includes taxes & fees
15 Dec - 16 Dec
Starlight Serenity - Hideaway with Stunning Views

Holiday Home in Upper Sugarloaf Key

10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is AU$2,632
includes taxes & fees
11 Dec - 12 Dec
Palm - Beach Houses Key West

Holiday Home in Upper Sugarloaf Key

9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is AU$2,497
includes taxes & fees
9 Dec - 10 Dec
The Lighthouse - Beach Houses Key West

Holiday Home in Sugarloaf Key

10.0 out of 10, Exceptional, (10)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is AU$3,760
includes taxes & fees
10 Dec - 11 Dec
Azucar - Beach Houses Key West

Holiday Home in Sugarloaf Key

8.0 out of 10, Very good, (2)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is AU$5,041
includes taxes & fees
27 Dec - 28 Dec
Hammock House - Beach Houses Key West

Holiday Home in Upper Sugarloaf Key

9.8 out of 10, Exceptional, (7)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is AU$3,666
includes taxes & fees
24 Dec - 25 Dec
The Hemingway - Beach Houses Key West

Houseboat in Stock Island

2.0 star property
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is AU$439
includes taxes & fees
1 Dec - 2 Dec
Aqua Lodges at Hurricane Hole Marina

Houseboat in Stock Island

7.8 out of 10, Good, (26)
"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 AU$781
includes taxes & fees
1 Dec - 2 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Cottage in Punta Brisa

2.5 star property
8.6 out of 10, Excellent, (273)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina

Cottage in Cudjoe Key

9.2 out of 10, Wonderful, (160)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
The price is AU$490
includes taxes & fees
7 Dec - 8 Dec
Cottage with Pool and Dockage, just minutes to Key West

Cottage in Cudjoe Key

8.2 out of 10, Very good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is AU$488
includes taxes & fees
9 Dec - 10 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (151)
"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 AU$391
includes taxes & fees
15 Dec - 16 Dec
Cottage with Pool and Boat Dockage just minutes to Key West!

Holiday Home in Summerland Key

9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is AU$839
includes taxes & fees
17 Dec - 18 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home in Cudjoe Key

9.6 out of 10, Exceptional, (100)
"Great location. "
United States
Davian k.
The price is AU$707
includes taxes & fees
7 Dec - 8 Dec
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Apartment in Old Town Key West

3.5 star property
8.4 out of 10, Very good, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is AU$463
includes taxes & fees
16 Dec - 17 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Holiday Home in Cudjoe Key

9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AU$863
includes taxes & fees
3 Dec - 4 Dec
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Holiday Home in Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AU$958
includes taxes & fees
30 Nov - 1 Dec
Island Time #110 Ocean Views - Cudjoe Key

Holiday Home in Cutthroat Harbor Estates

8.4 out of 10, Very good, (118)
"Great experience "
United States
Peyton S.
The price is AU$832
includes taxes & fees
7 Dec - 8 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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 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 favourite 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 depend 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 AU$419 per night. Entering your travel dates in the search wizard might find you 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.