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Sugarloaf Key Vacation Rentals

1 - 42 of 71 rentals
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Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - 190 195 190 - - - 195 225 225 225 225 260 -
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
99 99 99 99 - - - - - - - - - - - - -
The Ocean is Calling  - Marathon, FL Vacation Rental

The Ocean is Calling

Marathon, FL
5 Bed 3 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Turtle Key Complex - Islamorada, FL Vacation Rental

Turtle Key Complex

Islamorada, FL
6 Bed 6 Bath Sleeps 22 (20 Adults Max)
- - - - - - - - - - - - - - - - -
Breezy Palms & Tropical Charm - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Leatherback Cottage - Upper Unit - Islamorada, FL Vacation Rental
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Kemp's Cottage - Islamorada, FL Vacation Rental

Kemp's Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Ocean Oasis - Islamorada, FL Vacation Rental

Ocean Oasis

Islamorada, FL
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - - - 560 590
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
240 240 240 255 195 195 195 195 195 195 195 195 195 195 195 195 195
Sweet Serenity - Key Largo, FL Vacation Rental

Sweet Serenity

Key Largo, FL
3 Bed 2 Bath Sleeps 8
65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - 220 230 220 - -
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
190 235 235 195 180 180 180 180 220 220 180 180 180 180 180 220 220
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - 455
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
225 225 225 240 240 240 240 240 195 - - - - - - 225 240
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
275 235 - - - - - - - 190 225 225 225 215 - - -
Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
- - 460 485 - - - - - - - - - - - - 495
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
135 135 135 145 135 135 135 135 115 - - - - - - - 115
Hawksbill Cottage - Islamorada, FL Vacation Rental

Hawksbill Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 3 (2 Adults Max)
- - - - - - - - - - - - - - - - -
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
175 175 175 185 170 170 170 170 170 160 - - - - - - -
Green Turtle Cottage - Islamorada, FL Vacation Rental

Green Turtle Cottage

Islamorada, FL
2 Bed 1 Bath Sleeps 6 (4 Adults Max)
- - - - - - - - - - - - - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
90 90 90 99 99 99 99 99 99 99 99 99 99 99 99 99 99
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- 145 155 160 155 145 - - - - - - - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
- - 130 160 160 160 160 160 160 160 160 160 160 160 160 160 160
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
160 - - - - - - - 155 - - - - - - - 165
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
- - - - - - 220 230 195 - - - - - - - 190
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
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)
65 70 70 65 65 65 65 65 70 70 65 65 65 65 65 70 70
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - 115 120 99 - - - - - - - 99
White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
225 195 - - - - - - - - 190 190 - - - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
99 99 99 99 99 99 99 99 99 99 99 99 99 99 99 99 99
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
155 155 155 160 155 155 155 155 155 155 145 - - - - - -
Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - - - 250 265 265 265 265 265 265 265 265 265 265 265
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - 155 195 185 185 185 185 185 185 185 185 185 185 185 185 185
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - 175 195 195 195 195 190 - -
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- - - 140 150 150 150 150 150 150 150 140 - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - 160 170 170 170 145 - - - - - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- 99 - - - - - - - - - - - - - - -
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- - - - - - - 145 155 155 155 155 155 155 155 155 155
Tropical Charm - Key Colony Beach, FL Vacation Rental

Tropical Charm

Key Colony Beach, FL
3 Bed 3.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
185 185 185 195 195 195 195 195 195 195 195 195 195 195 195 195 195
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
- 99 99 - - - - - - - 99 99 99 99 99 99 99
Page 1 of 2

About Sugarloaf Key

Sugarloaf Key rated 4.4 out of 5 based on 35 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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