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Sugarloaf Key Vacation Rentals

1 - 42 of 66 rentals
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Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - 270 - - - 355 375 375 355 - - - - 395
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
- - - - - 99 115 99 99 99 99 99 99 99 99 99 99
Marathon Waterfront Recreational Paradise - Marathon, 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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Sunny Conch Getaway - Key West, FL Vacation Rental

Sunny Conch Getaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 190 195 195 195 195 195 190 190 190 190 190 190 190 195 195 195
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 295 - - - - 340 315 315 315 315 295 - - - - 285
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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The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - 185 - - - - - - - - - - -
White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
265 265 265 265 265 265 265 235 235 235 235 235 235 235 245 245 245
Sunnyside Canal  - Key Colony Beach, FL Vacation Rental

Sunnyside Canal

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
125 125 125 125 125 125 125 99 99 99 99 99 99 99 99 99 99
Landings of Largo Gem - Key Largo, FL Vacation Rental

Landings of Largo Gem

Key Largo, FL
2 Bed 2 Bath Sleeps 7 (4 Adults Max)
75 75 75 75 75 70 - - - - - - - 70 65 65 65
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
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Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
- - 165 170 170 145 - - - - - - - - - - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - 170 195 195 195
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
- 225 225 225 225 260 260 195 195 195 195 195 195 - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - 120 - - - - - - - 125 130 130
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
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Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
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Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - 315 330 285 - - - - - - - - - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - 160 170
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
170 170 170 170 170 170 170 160 160 160 160 160 160 160 160 - -
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- 180 - - - - 180 - - - - - - 145 - - -
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
- - - - - 140 150 140 140 140 140 140 120 - - - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - 240 250 250 265 265 265
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
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Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - - - - - - - - 99 125 - -
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - 140 - - - - - - - 145 150 150
Sunlit Serenity - Key Colony Beach, FL Vacation Rental

Sunlit Serenity

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
170 170 170 170 170 170 170 160 160 160 150 - - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
- - 115 120 120 120 120 99 99 99 99 99 99 99 99 99 99
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- 170 170 170 170 170 170 150 - - - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Floridian Fanfare - Key Colony Beach, FL Vacation Rental

Floridian Fanfare

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- 145 145 145 135 - - - - - - - - - - - -
White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
- 170 - - - - - - - 160 170 160 - - - - -
Breezy Palms - Key Colony Beach, FL Vacation Rental

Breezy Palms

Key Colony Beach, FL
4 Bed 4 Bath Sleeps 9
- - - - - 135 - - - - - - - - - - -
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About Sugarloaf Key

Sugarloaf Key rated 4.3 out of 5 based on 31 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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