Holiday Rentals in Sugarloaf Key

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Our top choices for Sugarloaf Key holiday rentals

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is €713
includes taxes & fees
14 Apr - 15 Apr
Starlight Serenity - Hideaway w Stunning Views

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (32 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 €435
includes taxes & fees
22 Apr - 23 Apr
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (181 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is €310
includes taxes & fees
3 May - 4 May
Aqua Lodges at Hurricane Hole Marina

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina
Stock Island
The price is €815
includes taxes & fees
13 Apr - 14 Apr
Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (316 reviews)
"Staff was great. Walking distance to No Name Pub. Water view was terrific. The bridge to nowhere was a good walk."
United States
Amado
The price is €269
includes taxes & fees
13 Apr - 14 Apr
Old Wooden Bridge Resort and Marina

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (57 reviews)
"The location was perfect for going in and out of Key West. The house was clean, spacious and comfortable. "
United States
Josie D.
The price is €344
includes taxes & fees
3 Apr - 4 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
8.8 out of 10, Excellent, (5 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 €331
includes taxes & fees
28 Apr - 29 Apr
Star Room Barnacle Resort

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (197 reviews)
"Excellent location for staying in the Lower Keys. Sunrise view. Nice neighborhood setting. Close to real good places to eat, listen to music and chill. Would come back. "
United States
Ihor C.
Direct Oceanfront Cottage-Sunrise View- #2,

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 €886
includes taxes & fees
5 Apr - 6 Apr
Atlantic View Luxury Villa with Pool

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is €432
includes taxes & fees
5 Apr - 6 Apr
Kelly's Kabin - Adorable Private Summerland Key Cottage

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (86 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is €422
includes taxes & fees
3 Apr - 4 Apr
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (101 reviews)
"Wonderful family getaway"
United States
Anthony V.
Old Florida Style, wrap around porch, boat basin for dockage, open water

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (22 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is €585
includes taxes & fees
13 Apr - 14 Apr
Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (155 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is €607
includes taxes & fees
5 Apr - 6 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (67 reviews)
"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "
United States
Paula D.
The price is €1,178
includes taxes & fees
6 Apr - 7 Apr
One of the very few beach houses with a daily, rental license in the Keys.

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (96 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is €674
includes taxes & fees
21 Apr - 22 Apr
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (36 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is €634
includes taxes & fees
13 Apr - 14 Apr
Paradise found

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (93 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is €393
includes taxes & fees
4 Apr - 5 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
Capmar House at Lunara Bay
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, 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 €227 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.