Sugarloaf Key Vacation Rentals

Compare 6 vacation rentals. Enter your trip dates to get started.
USA > Florida > Sugarloaf Key

Make Sugarloaf Key your next getaway—choose from 6 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

housing_type_house.jpg

House rentals

View 5 House rentals
housing_type_cottage.jpg

Cottages

View 1 Cottages

Sugarloaf Key vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Pelico Palms 3D Tour
8 Bed | 7 Bath | Sleeps 20 (14 Adults Max)

Pelico Palms - Sugarloaf Key, FL

From $1,143
Villa of the Setting Sun
4 Bed | 4.5 Bath | Sleeps 8

Villa of the Setting Sun - Sugarloaf Key, FL

From $1,915
Pelico Paradise 3D Tour
5 Bed | 3.5 Bath | Sleeps 10

Pelico Paradise - Sugarloaf Key, FL

From $575
Pelico Palms - Sunset Cottage 3D Tour
2 Bed | 2 Bath | Sleeps 5

Pelico Palms - Sunset Cottage - Sugarloaf Key, FL

From $271
Pelico Palms - Villa  & Treehouse
6 Bed | 5 Bath | Sleeps 16 (9 Adults Max)

Pelico Palms - Villa & Treehouse - Sugarloaf Key, FL

From $995

View 1 more homes

Recent Sugarloaf Key vacation rental reviews

Great location, beautiful scenery, private and well appointed. The photos on line do not render the place justice, it's much better in real life.
Timm O. | Sep 2021
Very relaxing secluded home close to the Keys! Worked out great! Resort style!
Paul L. | Aug 2021
Amazing home, seclusion, natural habitat and amazingly responsive customer service to a few small issues with storm related items. Great job Vacasa! We would highly recommend this property and property manager. Thanks Carol at Vacasa, you were so kind!!
Steve W. | Jul 2021

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

4 Florida Keys Races and Marathons for Every Skill Level

Photo credit: flickr user donielle