Sugarloaf Key Vacation Rentals

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USA > Florida > Sugarloaf Key

Make Sugarloaf Key your next getaway—choose from 7 great vacation rentals

Let the tropical island trio of warm breezes, white sand beaches, and fun in the sun guide you to deep relaxation in one of our Sugarloaf Key vacation rentals. 

Explore Sugarloaf Key house rentals, cottages, and more

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House rentals

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Cottages

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Sugarloaf Key vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Pelico Palms
8 Bedroom | 7 Bath | Sleeps 20 (14 Adults Max)

Pelico Palms - Sugarloaf Key, FL

$1,987 avg / night
Pelico Palms - Sunset Cottage
2 Bedroom | 2 Bath | Sleeps 5

Pelico Palms - Sunset Cottage - Sugarloaf Key, FL

$434 avg / night
Pelico Palms - Villa
4 Bedroom | 4 Bath | Sleeps 12 (7 Adults Max)

Pelico Palms - Villa - Sugarloaf Key, FL

$1,149 avg / night
Villa of the Setting Sun
4 Bedroom | 4.5 Bath | Sleeps 8

Villa of the Setting Sun - Sugarloaf Key, FL

$2,513 avg / night
Pelico Palms - Villa  & Treehouse
6 Bedroom | 5 Bath | Sleeps 16 (9 Adults Max)

Pelico Palms - Villa & Treehouse - Sugarloaf Key, FL

$1,650 avg / night

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Recent Sugarloaf Key vacation rental reviews

The location is wonderful. There were no problems with the kitchen. The beds were comfortable.
RICHARD W. | Aug 2022
Has something for everyone, the nature and pool and home are stunning and well maintained. Be sure to bring extra trash bags and seasonings for the kitchen only thing we needed! We will be back
Monica R. | Aug 2022
The house was set up really nice and the stay was comfortable. Had a few minor issues upon arrival but they came right out and took great care of it.
Autumn R. | Jul 2022
Sugarloaf Key Frequently Asked Questions

Yes, 7 of our Sugarloaf Key homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 20 of our Sugarloaf Key vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Sugarloaf Key vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Sugarloaf Key team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Sugarloaf Key, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Deriving its name from a type of pineapple once grown in the area, Sugarloaf Key is comprised of an upper and lower island and belongs to Florida’s lower keys. The area’s abundant wildlife and great fishing make it a sportsman’s paradise, while the white sand beaches and laid-back island atmosphere appeals to casual vacationers including families, couples, and retirees.

Things to Do in Sugarloaf Key, FL

Located between Saddlebunch Keys to the west and Cudjoe Key to the east, both upper and lower islands of Sugarloaf Key sit on open, shallow waters that play host to world-class sport-fishing. Home to tarpon, bonefish, grouper and many more large fish species, this area is particularly well-suited for those looking to land a trophy fish. Hire a guide for the day at any of the island’s fishing charters, and head out by boat to the area's prime fishing grounds, known as flats, where you’ll hook a 150-pound tarpon and have the fight of a lifetime trying to reel it in. 

Non-fisherfolk will also find plenty to do! Rent kayaks and paddle into the Upper Sugarloaf Sound, where you can the explore mangrove swamp coastline alongside dolphins playing in the surf. If you prefer to have your adventures on land, grab your family and head down to see the Sugarloaf Key Bat Tower a tower built in 1929 to entice bats and provide a solution to the area’s mosquito problem. Kids will love watching the bats fly frenetically around the structure, catching insects in mid-flight. 

Day Trips from Sugarloaf Key

Our Florida Keys vacation rentals in Sugarloaf Key are only 15 miles from the region's biggest draw: Key West. Head into the larger city for an afternoon touring the Hemingway Home & Museum, then take in the sunset and spectacle at Mallory Square Dock. Grab a margarita and some fresh fish tacos at one of the local restaurants...unless your fridge back in Sugarloaf Key is full of your own daily catch! 

Want to avoid the Key West crowds? Head 15 miles back toward the mainland to the kayaking, scuba, and snorkeling paradise surrounding Big Pine. Divers can explore the undersea wreckage of the Adolphus Bush, and snorkelers will be well-rewarded with a trip out to the coral reefs at Looe Key.

For a fantastic home base with direct access to the best of Florida’s world-class fishing and island adventure, a stay in one of our Sugarloaf Key vacation rentals can’t be beat! 

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Photo credit: flickr user donielle