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Sugarloaf Key Rentals

1 - 42 of 307 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 - - - - 296 323 327 306 - - - 296 325 328 307
Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
294 - - - - - - - 330 349 358 330 - - - - 285
 Modern Rendezvous  - Key West, FL Vacation Rental

Modern Rendezvous

Key West, FL
2 Bed 2 Bath Sleeps 4
983 962 957 949 985 975 1061 939 950 953 975 1050 1034 946 950 955 959
Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
158 163 153 - - - 171 158 151 - - - - - - - 145
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- 124 130 122 - - 136 114 - - - - - 118 126 120 -
Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
461 459 460 458 403 - - - - - - - - - - - -
Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
168 164 163 162 168 166 181 160 162 163 166 179 176 161 162 163 164
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
158 163 162 152 - - - - 144 - - - - - - - 145
Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
176 181 180 178 158 - - - - - - 161 - - - - 145
Truman @ Duval - One Bedroom - Key West, FL Vacation Rental
172 167 166 164 172 170 186 159 161 162 167 184 180 160 161 163 164
Banana Breeze @ Key Cove - Key West, FL Vacation Rental

Banana Breeze @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
214 204 199 193 - - - - - - - - - - - - -
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - 200 - - - - - - - 191 - - -
Casa Hueso - Key West, FL Vacation Rental

Casa Hueso

Key West, FL
4 Bed 3.5 Bath Sleeps 8
182 161 151 161 208 205 243 200 204 204 212 223 217 193 185 205 207
Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

Key West, FL
1 Bed 1 Bath Sleeps 4
117 115 114 113 117 116 126 112 113 113 116 125 123 113 113 114 114
Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
242 230 224 230 272 270 301 276 278 279 283 289 286 273 268 279 280
Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
476 487 483 450 - - - 426 435 - - - - - - - 421
Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - 120 -
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 119 - - 136 121 123 117 - - - - - - -
Key West Interlude - Key West, FL Vacation Rental

Key West Interlude

Key West, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Commodore's Cove - Key West, FL Vacation Rental

Commodore's Cove

Key West, FL
4 Bed 4 Bath Sleeps 12
- - - 429 - - - 426 435 - - - - - - - 421
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - 192 180 182 182 186 163 - - - - -
Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
126 - - 119 - - 143 127 130 123 - - - 122 130 131 124
Bay Harbor View - Key West, FL Vacation Rental

Bay Harbor View

Key West, FL
5 Bed 3 Bath Sleeps 18
- - - - - - - - - - - - - - - - -
Secret Garden - Key West, FL Vacation Rental

Secret Garden

Key West, FL
2 Bed 1 Bath Sleeps 4
169 152 144 144 - - - - - - - - - - - - -
Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
165 145 136 146 193 180 - - - - - - - - - - -
Caribbean Dreams - Key West, FL Vacation Rental

Caribbean Dreams

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - 139 124 126 126 123 - - 118 126 127 128
Fantastic Fifth Street - Key Colony Beach, FL Vacation Rental

Fantastic Fifth Street

Key Colony Beach, FL
4 Bed 2.5 Bath Sleeps 10
- - - - - 129 - - - - - - - - - - -
Truman @ Duval - Studio - Key West, FL Vacation Rental

Truman @ Duval - Studio

Key West, FL
0 Bed 1 Bath Sleeps 2
163 167 166 164 146 - 177 159 161 162 167 184 180 160 161 163 164
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - 119 106 102 - - - - 101 108 108 103
Anchors Aweigh Retreat - Marathon, FL Vacation Rental

Anchors Aweigh Retreat

Marathon, FL
2 Bed 2 Bath Sleeps 6 (5 Adults Max)
133 133 126 - - - - - 158 166 167 135 - - - - -
Sombrero Siesta - Marathon, FL Vacation Rental

Sombrero Siesta

Marathon, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
238 226 221 227 268 266 296 272 261 - - - - - - - -
Bahama House - Key West, FL Vacation Rental

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
- 413 398 - - - - - - - - - - - 432 462 -
Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
179 162 162 162 210 206 215 200 205 205 214 215 215 200 200 206 208
Cozumel Suite #112 - Key West, FL Vacation Rental

Cozumel Suite #112

Key West, FL
2 Bed 2 Bath Sleeps 6
163 149 - - - - - - - - - - - 161 165 178 179
Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
119 - - - - - 136 115 - - - - - - - 117 118
Live Laugh Love - Marathon, FL Vacation Rental

Live Laugh Love

Marathon, FL
2 Bed 2 Bath Sleeps 4
148 148 148 147 150 159 167 167 166 166 167 159 168 168 169 168 169
Shipyard Perch  - Key West, FL Vacation Rental

Shipyard Perch

Key West, FL
2 Bed 2 Bath Sleeps 4
- - - - - 188 242 - - - - - - - 178 191 -
Paradise Escape #407 - Key West, FL Vacation Rental

Paradise Escape #407

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Sunset Marina View - Key West, FL Vacation Rental

Sunset Marina View

Key West, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
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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