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Islamorada Vacation Rentals

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Island Gem - Islamorada, FL Vacation Rental

Island Gem

Islamorada, FL
2 Bed 2 Bath Sleeps 6
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Ocean Oasis - Islamorada, FL Vacation Rental

Ocean Oasis

Islamorada, FL
5 Bed 4 Bath Sleeps 14
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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 #4 - Islands in the Stream - Key West, FL Vacation Rental
- - 153 155 - - - 187 192 191 189 167 - - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 139 143 142 133 - - 143 127 130 130
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 - - - -
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  - Garden of Eden - Key West, FL Vacation Rental
- 284 - - - - - 312 - - - - - - - 330 349
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
119 - - - - - - - - - 126 - - 143 127 130 123
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
Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
244 237 228 236 263 261 255 249 238 238 257 288 286 301 276 278 279
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
132 131 132 125 - - - - - - - - - - - - -
Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
- 237 - - - - - - - 230 - - - 297 275 279 264
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
Shark Key Chateau - Key West, FL Vacation Rental

Shark Key Chateau

Key West, FL
5 Bed 4.5 Bath Sleeps 12
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - - - - - - 167 173 162 - - - 171 158 151 -
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
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
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
Dream in the Keys - Key Colony Beach, FL Vacation Rental

Dream in the Keys

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
205 204 204 205 204 210 213 225 225 225 224 225 228 228 229 228 228
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
Tsalta - Key West, FL Vacation Rental

Tsalta

Key West, FL
3 Bed 3 Bath Sleeps 8
- 233 213 229 287 284 271 243 222 217 255 263 259 287 241 245 246
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 - - - - -
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
- - - 147 - - - 167 173 172 161 - - - - 144 -
Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- 157 142 155 200 198 187 162 145 144 177 204 190 - - - -
Bonaire Suite #210 - Key West, FL Vacation Rental

Bonaire Suite #210

Key West, FL
2 Bed 2 Bath Sleeps 6
- 158 156 156 - - - 164 161 152 - - - 190 174 177 167
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
A Key Escape - Key West, FL Vacation Rental

A Key Escape

Key West, FL
3 Bed 2.5 Bath Sleeps 8
- - - 413 - - - - - - - - - 497 - - -
Casa Hermosa - Key West, FL Vacation Rental

Casa Hermosa

Key West, FL
2 Bed 2 Bath Sleeps 5
141 142 135 - - - - - - - - - - - - - -
Lorelane Lookout - Key Largo, FL Vacation Rental

Lorelane Lookout

Key Largo, FL
4 Bed 2.5 Bath Sleeps 9
- - 114 114 117 121 124 126 123 122 117 120 120 118 115 114 115
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - 139 143 142 133 - - 143 120 - -
Amelia House - Key West, FL Vacation Rental

Amelia House

Key West, FL
3 Bed 2 Bath Sleeps 8
431 415 395 412 403 - - - - 389 454 390 - - - - -
Casa Caribe @ Duval Square - Key West, FL Vacation Rental

Casa Caribe @ Duval Square

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- 249 248 247 - - - - - - - - - 297 275 279 264
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - 119 106 102 -
Fantastic Fifth Street - Key Colony Beach, FL Vacation Rental

Fantastic Fifth Street

Key Colony Beach, FL
4 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - 136 - - - -
Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

Key West, FL
2 Bed 2.5 Bath Sleeps 4
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Key West Nest  - Key West, FL Vacation Rental

Key West Nest

Key West, FL
3 Bed 2 Bath Sleeps 6
178 179 180 183 206 203 193 199 192 191 188 200 196 205 168 172 172
Casa Hueso - Key West, FL Vacation Rental

Casa Hueso

Key West, FL
4 Bed 3.5 Bath Sleeps 8
186 173 158 171 220 217 206 180 161 160 195 221 217 243 200 204 204
Margarita Suite #305 - Key West, FL Vacation Rental

Margarita Suite #305

Key West, FL
2 Bed 2 Bath Sleeps 6
166 158 - - - - - - - 144 - - - - - - -
Casa Bonita @ Duval Square R1 - Key West, FL Vacation Rental
- - 229 - - - - 252 - - - - - 297 281 284 269
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About Islamorada

Quaint island living, plenty of fun in the sun activities, and access to world-class sport fishing are ready to greet you when you stay at one of our Islamorada vacation rentals. Islamorada is a popular destination for those seeking year-round warm weather, beautiful white sand beaches, and a laid-back island vibe. 

Things to Do in Islamorada, FL

Located between the Florida Key islands of Key Largo to the east and Marathon Key to the west, Islamorada offers a wide range of activities from snorkeling to paragliding to landing trophy tarpon and marlin in the area’s warm coastal waters, making it well-suited for adventurers and families.

Kids will love interacting with the area’s abundant sea life at the Theater of the Sea marine mammal park, where they can toss mackerel to hungry sea lions, swim with dolphins, and get up close to endangered sea turtles. They might also enjoy learning about the island’s mangrove swamps and exotic coastal habitat aboard a Family Fun Boat Tour, where they’ll surely have close encounters with egrets, herons, gulls, and other avian residents of the island!

For more adult tastes, Islamorada offers a plethora of lively options, ranging from great dining at any of the area’s fresh-from-the-boat seafood restaurants to live reggae, bluegrass, and other music festivals throughout the year at ICE Amphitheater at Founder’s Park on Plantation Key. Whatever your vacation plans may entail, a stay in one of our Florida Keys vacation rentals in Islamorada provides an excellent home base!

Outdoor Adventures in Islamorada, FL

For those who like to get out and explore nature, Islamorada offers unmatched access to a wide range of activities on both land and water. Take a self-guided walk through lush nature trails on 965 acres of pristine old growth mangrove, mahogany, and poisonwood marshland at Long Key State Park, or unearth buried treasure and artifacts from a Spanish ship that sunk in 1733 at Indian Key Historic State Park. If you prefer to stay dry, rent kayaks or a boat to tour the ancient coral reef and the tropical forest that thrives above at the Lignumvitae Key Botanical State Park on tiny Lignumvitae Key.

Day Trips from Islamorada, FL

On the north end of the key islands, Islamorada offers quick access to the mainland, which is only 40 miles to the north. Drive north another 40 miles to arrive in Miami, a city known for its thriving nightlife, great shopping, and Latin-focused dining. Thousands of acres of swampland that are home to alligators, cranes, snakes, and many other native species await only 53 miles away at Everglades National Park. Marathon, Big Pine, Sugarloaf, and Key West islands all lie within 80 miles of Islamorada.

For a fantastic home base in the Florida Keys, a stay in any of our Islamorada vacation rentals is one you won’t soon forget!

Photo credit: Jon Bilous via Shutterstock

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