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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
- - 164 - - - - - 174 - - - - 296 323 327 306
Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
- 284 - - - - - 312 - - - - - - - 330 349
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - 205 232 247 - - - - - - - 212 - - - -
Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 133 - - 126 - - 143 127 130 123
Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

Key West, FL
1 Bed 1 Bath Sleeps 4
113 113 114 115 124 123 119 124 121 121 120 124 123 126 112 113 113
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - - - - - 163 181 181 181 178 153 - - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 139 143 142 133 - - 143 127 130 130
Key West Interlude - Key West, FL Vacation Rental

Key West Interlude

Key West, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 133 - - - - - 137 - - -
Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
240 233 225 232 259 257 251 245 235 234 253 284 281 296 272 261 -
Cindy Villa  - Key Largo, FL Vacation Rental

Cindy Villa

Key Largo, FL
1 Bed 1 Bath Sleeps 2
49 49 49 49 52 53 53 55 54 54 53 54 54 53 52 52 52
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - 119 106 102 -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - 192 180 182 182
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
119 - - - - - - - - - 126 - - 143 127 130 123
Hibiscus Room - Key West, FL Vacation Rental

Hibiscus Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 139 143 142 133 - - 143 127 130 123
Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
- - - - - 150 171 178 174 173 171 178 176 181 160 162 163
Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
- - 153 155 - - - 187 192 191 189 167 - - - - -
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- - - - - 379 - - - - - - - - - - -
Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
- 237 - - - - - - - 230 - - - 297 275 279 264
Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
162 - - 163 179 179 179 179 162 162 179 215 215 215 200 205 205
Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - 119 - - - - -
Garden of Roses - Key West, FL Vacation Rental

Garden of Roses

Key West, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - 140 145 153 - - -
Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
- - - 147 - - - 167 173 172 161 - - - - 144 -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - 133 134 - - 141 166 166 166 166
Toon Hall - Tropical Village - Key West, FL Vacation Rental
366 367 344 344 - - - 362 355 353 384 - - 399 - - -
Duval Corner - Key West, FL Vacation Rental

Duval Corner

Key West, FL
1 Bed 1 Bath Sleeps 4
- - 145 - - - - - 161 161 - - - - 149 160 160
Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - - - - - - 167 173 162 - - - 171 158 151 -
The Ocean is Calling  - Marathon, FL Vacation Rental

The Ocean is Calling

Marathon, FL
5 Bed 4 Bath Sleeps 12
291 303 304 288 - - - - - - - 293 - - - - -
Margarita Suite #305 - Key West, FL Vacation Rental

Margarita Suite #305

Key West, FL
2 Bed 2 Bath Sleeps 6
166 158 - - - - - - - 144 - - - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Casa Atlantic - Key West, FL Vacation Rental

Casa Atlantic

Key West, FL
3 Bed 3 Bath Sleeps 9
236 221 204 219 274 271 259 230 209 208 247 251 247 275 230 234 235
Casa Key West @ Duval Square - Key West, FL Vacation Rental
422 378 - - - - - - - 364 419 - - 457 418 424 402
Island Gem - Islamorada, FL Vacation Rental

Island Gem

Islamorada, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

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

Bay Harbor View

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

Passover Cottage

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - 389 387 - - - 486 444 426 -
Bermuda Suite - Key West, FL Vacation Rental

Bermuda Suite

Key West, FL
1 Bed 1.5 Bath Sleeps 4
- - - - - - - - - 174 171 - - - - 156 157
Flagler's Crossing - Key West, FL Vacation Rental

Flagler's Crossing

Key West, FL
2 Bed 2.5 Bath Sleeps 6
135 128 120 127 153 152 146 134 124 123 142 160 158 172 149 151 151
Bahama House - Key West, FL Vacation Rental

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - 423 421 - - - - - - -
 Paradise Escape #407 - Key West, FL Vacation Rental

Paradise Escape #407

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Page 1 of 8

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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