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Sugarloaf Key Rentals

1 - 42 of 295 rentals
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Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
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The Ocean is Calling  - Marathon, FL Vacation Rental

The Ocean is Calling

Marathon, FL
5 Bed 4 Bath Sleeps 12
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Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
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Key West Interlude - Key West, FL Vacation Rental

Key West Interlude

Key West, FL
3 Bed 2 Bath Sleeps 6
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Sunlit Serenity - Key Colony Beach, FL Vacation Rental

Sunlit Serenity

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
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Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
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*Paradise Found*  - Cudjoe Key, FL Vacation Rental

*Paradise Found*

Cudjoe Key, FL
3 Bed 2 Bath Sleeps 6
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Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Coconut Palm  - Key West, FL Vacation Rental

Coconut Palm

Key West, FL
3 Bed 2 Bath Sleeps 6
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Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
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Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
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Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
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No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
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Bahama House - Key West, FL Vacation Rental

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
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The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Bermuda Suite - Key West, FL Vacation Rental

Bermuda Suite

Key West, FL
1 Bed 1.5 Bath Sleeps 4
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Trinidad Suite #105 - Key West, FL Vacation Rental

Trinidad Suite #105

Key West, FL
2 Bed 2 Bath Sleeps 6
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Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
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Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

Key West, FL
2 Bed 2.5 Bath Sleeps 4
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Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
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Canal-side Charisma - Key Colony Beach, FL Vacation Rental
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Island Gem - Islamorada, FL Vacation Rental

Island Gem

Islamorada, FL
2 Bed 2 Bath Sleeps 6
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Verano Villa - Summerland Key, FL Vacation Rental

Verano Villa

Summerland Key, FL
3 Bed 2 Bath Sleeps 6
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Coastal Comfort @ Key Cove - Key West, FL Vacation Rental

Coastal Comfort @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
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Curry House Room 4 - Key West, FL Vacation Rental

Curry House Room 4

Key West, FL
0 Bed 1 Bath Sleeps 2
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Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
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Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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Casa Bonita @ Duval Square R1 - Key West, FL Vacation Rental
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Yellowfin Ledge On Duval - Key West, FL Vacation Rental

Yellowfin Ledge On Duval

Key West, FL
1 Bed 1 Bath Sleeps 3
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Tobago Grande - Key West, FL Vacation Rental

Tobago Grande

Key West, FL
3 Bed 3 Bath Sleeps 6
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Secret Garden - Key West, FL Vacation Rental

Secret Garden

Key West, FL
2 Bed 1 Bath Sleeps 4
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Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
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Banana Breeze @ Key Cove - Key West, FL Vacation Rental

Banana Breeze @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
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Heron Hideaway - Key West, FL Vacation Rental

Heron Hideaway

Key West, FL
1 Bed 1 Bath Sleeps 4
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Olivia Street Retreat - Key West, FL Vacation Rental

Olivia Street Retreat

Key West, FL
1 Bed 1 Bath Sleeps 4
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Saint Thomas Suite #302 - Key West, FL Vacation Rental

Saint Thomas Suite #302

Key West, FL
2 Bed 2 Bath Sleeps 6
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A Key Escape - Key West, FL Vacation Rental

A Key Escape

Key West, FL
3 Bed 2.5 Bath Sleeps 8
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Key West Nest  - Key West, FL Vacation Rental

Key West Nest

Key West, FL
3 Bed 2 Bath Sleeps 6
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Sunshine House - Key West, FL Vacation Rental

Sunshine House

Key West, FL
1 Bed 1 Bath Sleeps 4
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Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
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About Sugarloaf Key

Sugarloaf Key rated 4.3 out of 5 based on 45 reviews Sugarloaf key, FL

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. 

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! 

Photo credit: flickr user donielle

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