Sugarloaf Key Vacation Rentals

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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


House rentals

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Sugarloaf Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Pelico Paradise 3D Tour
5 Bedroom | 3.5 Bath | Sleeps 10

Pelico Paradise - Sugarloaf Key, FL

From $450
Pelico Palms - Villa 3D Tour
4 Bedroom | 4 Bath | Sleeps 12 (7 Adults Max)

Pelico Palms - Villa - Sugarloaf Key, FL

From $550
Pelico Palms - Sunset Cottage 3D Tour
2 Bedroom | 2 Bath | Sleeps 5

Pelico Palms - Sunset Cottage - Sugarloaf Key, FL

From $249
Pelico Palms - Villa  & Treehouse
6 Bedroom | 5 Bath | Sleeps 16 (9 Adults Max)

Pelico Palms - Villa & Treehouse - Sugarloaf Key, FL

From $845
Villa of the Setting Sun 3D Tour
4 Bedroom | 4.5 Bath | Sleeps 8

Villa of the Setting Sun - Sugarloaf Key, FL

From $1,500

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Recent Sugarloaf Key vacation rental reviews

The house, cleanliness, spaciousness, beautiful views, amenities, everything about the property was five stars.
J F D. | May 2022
The 5 bedroom house had plenty of rooms for our family's vacation. There was a large dinning room and living room. There is a washer and dryer, too! The yard had plenty of space for lots of vehicles and accessories. The house and property is very nice, but you can tell they are in the middle of improving it. Like new trees outside (old ones tossed in a pile) and 2 piles of rocks. As for inside, there were a few items that needed replacing (2 balcony doors didn't open, but replacement ones were outside), a new couch, etc, but it was good for our purpose. Would love to go back when it is all done!
Jody H. | Apr 2022
We loved the quiet dead end street and how the house is surrounded by bushes, palm trees and other greenery. The shared pool ia also a lovely space, surrounded by greenery, flowers a flowing waterfall and a cabana with a outdoor couch and lounge chairs.
Janine V. | Apr 2022

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! 

Discover Sugarloaf Key

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Photo credit: flickr user donielle