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Key West Vacation Rentals

1 - 42 of 305 rentals
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
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Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
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Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 128 132 - - - -
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
293 305 - - - - - - - - - - - - - - 238
Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
- - - 565 - 491 496 - - - - 432 - - - - -
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
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A Key Escape - Key West, FL Vacation Rental

A Key Escape

Key West, FL
3 Bed 2.5 Bath Sleeps 8
580 - - 611 539 - - - - - - 477 491 - - - -
Carriage Courtyard  - Key West, FL Vacation Rental

Carriage Courtyard

Key West, FL
3 Bed 2 Bath Sleeps 6
258 272 272 288 288 246 255 297 302 301 286 276 272 - - - -
Canalside in the Keys - Key West, FL Vacation Rental

Canalside in the Keys

Key West, FL
2 Bed 2 Bath Sleeps 6
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Casa Atlantic - Key West, FL Vacation Rental

Casa Atlantic

Key West, FL
3 Bed 3 Bath Sleeps 9
276 336 335 330 278 213 221 261 267 266 251 242 251 252 255 271 263
Bay Harbor View - Key West, FL Vacation Rental

Bay Harbor View

Key West, FL
5 Bed 3 Bath Sleeps 18
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Casa Caribe @ Duval Square - Key West, FL Vacation Rental

Casa Caribe @ Duval Square

Key West, FL
2 Bed 2.5 Bath Sleeps 6
297 - - - - - - - - - - - - - - - -
Caribbean Fling - Key West, FL Vacation Rental

Caribbean Fling

Key West, FL
2 Bed 1.5 Bath Sleeps 6
213 213 213 225 195 170 172 171 176 174 164 158 164 165 167 177 172
Banana Breeze @ Key Cove - Key West, FL Vacation Rental

Banana Breeze @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
246 273 272 277 253 237 240 260 263 263 256 251 256 256 257 265 261
Casa Hermosa - Key West, FL Vacation Rental

Casa Hermosa

Key West, FL
2 Bed 2 Bath Sleeps 5
- - - - - 162 172 171 176 174 164 158 164 165 167 177 172
Gardenia Getaway - Key West, FL Vacation Rental

Gardenia Getaway

Key West, FL
1 Bed 1 Bath Sleeps 4
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Saint Lucia Suite #201 - Key West, FL Vacation Rental

Saint Lucia Suite #201

Key West, FL
2 Bed 2 Bath Sleeps 6
172 - - 202 183 164 161 - - - - - - - 171 - -
Nautical Wheeler  - Key West, FL Vacation Rental

Nautical Wheeler

Key West, FL
4 Bed 3 Bath Sleeps 8
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Commodore's Cove - Key West, FL Vacation Rental

Commodore's Cove

Key West, FL
4 Bed 4 Bath Sleeps 12
- - - 565 - - 496 495 - - - 432 - - - - -
Monroe Suite  - Key West, FL Vacation Rental

Monroe Suite

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 135 - - - - - - - - - - - - -
Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - 121 - - - - - 164 180 181 183 196 190
The Frontier Suite - Key West, FL Vacation Rental

The Frontier Suite

Key West, FL
2 Bed 2 Bath Sleeps 6
136 139 139 141 121 99 106 99 108 107 99 - - - - - 91
Rum Cay Suite #304 - Key West, FL Vacation Rental

Rum Cay Suite #304

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - 165 - - - - - - - - - - - -
Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

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

Paradise Suite

Key West, FL
1 Bed 1.5 Bath Sleeps 4
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West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
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Bonaire Suite #210 - Key West, FL Vacation Rental

Bonaire Suite #210

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - 202 183 164 169 184 - - - - - - - - -
Duval Corner - Key West, FL Vacation Rental

Duval Corner

Key West, FL
1 Bed 1 Bath Sleeps 4
- - - - 178 163 - - - - - - - - - - -
Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
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Casa Key West @ Duval Square - Key West, FL Vacation Rental
- - - 537 488 394 386 - - - - - 406 - - - -
Poolside Suite - Key West, FL Vacation Rental

Poolside Suite

Key West, FL
2 Bed 1 Bath Sleeps 6
- - - - - - 213 - - - - - - - - - -
Tropical Retreat  - Key West, FL Vacation Rental

Tropical Retreat

Key West, FL
3 Bed 3.5 Bath Sleeps 8
534 - - - - - - - - - - 483 499 - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - 139 143 138 - - - - - - - - - -
Southern Cross - Tropical Village - Key West, FL Vacation Rental
- - - - 290 216 - - - - - - - - - - -
Toon Hall - Tropical Village - Key West, FL Vacation Rental
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Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - 355 - - - - - - - - - - -
Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - 164 149 140 - - - - - - - - - - -
Waterfall 4 - Key West, FL Vacation Rental

Waterfall 4

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 126 - - - - - - - - - - - - -
Secret Garden - Key West, FL Vacation Rental

Secret Garden

Key West, FL
2 Bed 1 Bath Sleeps 4
180 219 218 215 182 174 172 - - - - - - - 198 221 214
Southern Comfort @ Key Cove - Key West, FL Vacation Rental

Southern Comfort @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
249 277 277 282 257 240 245 264 266 266 259 255 259 259 261 268 265
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About Key West

For an island that is only two miles long and four miles wide, you'd think it would be a quiet place, demanding long trips outside the immediate area to reach attractions, good food, and historical sites. However, that's far from the case when you book one of our Key West vacation rentals! With a vibrant arts culture, a variety of opportunities for outdoor adventures, and a welcoming small-town attitude, Key West promises a unique and memorable vacation

When you book a stay in one of our Florida vacation rentals in Key West, you're not just booking a vacation - you're booking an experience!

Where is Key West, FL? 

Our Key West vacation rentals are on the last island of the Florida Keys chain, about 160 miles from Miami and 98 miles from Key Largo. Whether you chose to arrive at this interesting island via plane, ferry, or car, the first sight of the expansive Atlantic Ocean promises to take your breath away. With its vibrant wildlife, you may even be lucky enough to spot a few dolphins splashing around and welcoming you to Key West!

Things to Do in Key West, FL

Although the island is relatively small, the number of attractions are vast and varied! Key West has a diverse arts and history culture, including plenty of galleries, delicious restaurants, and landmarks that are as unique as the Keys themselves. The Hemingway Home, located in Old Key West, is a historical treat for guests who enjoy literature (and six-toed cats). With look-out towers and detailed exhibits of the wrecking business, the Shipwreck Museum is definitely worth a visit.

Other points of interest on the island include the Southernmost Point, and Wyland's Whaling Wall, a gorgeous mural of some of Key West's local aquatic residents. Key West has a laid-back attitude, but its nightlife isn't lacking! Let loose on Duval Street, starting in Mallory Square with its famous Sunset Celebration and working your way down the main drag to the (in)famous Sloppy Joe's. 

Feeling hungry after a long day full of excitement and adventure? Our Key West lodging is conveniently close to many dining options, including restaurants like Help Yourself, an organic cafe and juice bar, and Square One, a fine-dining establishment. 

Outdoor Activities in Key West, FL

With so many diverse outdoor activities near our Key West vacation rentals, it might be difficult to decide where to start. However, one thing is for sure - water is Key West's playground! Book a charter with Sunset Sail Key West and admire the wildlife or catch one of those famous Florida sunsets. With early morning sunrise cruises, starlit float trips, snorkeling, and themes like "Cruise Concert" and "Wine and Wind" at dusk, there's something for everyone! 

While sandy beaches are not as common in the Keys due to the reef barrier, there are a few favorites that are worth a visit, including Smathers Beach, Ft. Zachary Taylor State Park, and the Dry Tortugas National Park, home to epic sandy beaches and historic Fort Jefferson. 

The natural beauty of Key West has been preserved thanks to the recent emphasis placed on ecotourism. With options for kayaking, scuba diving, or snorkeling, you'll be able to admire wildlife in its natural habitat while helping conservation efforts to maintain the Keys. View the reef up close with a trip on a glass-bottom boat, or try a dolphin-viewing charter!

A vacation destination that combines the modern conveniences and comforts of home with a growing environmental awareness (and a memorable nightlife scene!), this beautiful island offers a glimpse into all that Florida has to offer. Plan a visit to one of our Key West vacation rentals for a memorable trip full of relaxation, exploration, and unforgettable experiences. 

Photo credit: Fotoluminate LLC via Shutterstock

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