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Sugarloaf Key Rentals

1 - 42 of 301 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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Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
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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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Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
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Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

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

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
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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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Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
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Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
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Cindy Villa  - Key Largo, FL Vacation Rental

Cindy Villa

Key Largo, FL
1 Bed 1 Bath Sleeps 2
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Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

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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West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
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Hibiscus Room - Key West, FL Vacation Rental

Hibiscus Room

Key West, FL
0 Bed 1 Bath Sleeps 2
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Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
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Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
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Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
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Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
2 Bed 2 Bath Sleeps 6
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Garden of Roses - Key West, FL Vacation Rental

Garden of Roses

Key West, FL
3 Bed 2 Bath Sleeps 8
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Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
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Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
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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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Toon Hall - Tropical Village - Key West, FL Vacation Rental
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Duval Corner - Key West, FL Vacation Rental

Duval Corner

Key West, FL
1 Bed 1 Bath Sleeps 4
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
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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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Margarita Suite #305 - Key West, FL Vacation Rental

Margarita Suite #305

Key West, FL
2 Bed 2 Bath Sleeps 6
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Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Casa Atlantic - Key West, FL Vacation Rental

Casa Atlantic

Key West, FL
3 Bed 3 Bath Sleeps 9
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Casa Key West @ Duval Square - Key West, 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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Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

Key West, FL
2 Bed 2.5 Bath Sleeps 4
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Bay Harbor View - Key West, FL Vacation Rental

Bay Harbor View

Key West, FL
5 Bed 3 Bath Sleeps 18
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Passover Cottage - Key West, FL Vacation Rental

Passover Cottage

Key West, 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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Flagler's Crossing - Key West, FL Vacation Rental

Flagler's Crossing

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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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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 Paradise Escape #407 - Key West, FL Vacation Rental

Paradise Escape #407

Key West, FL
2 Bed 2 Bath Sleeps 6
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About Sugarloaf Key

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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