Language and Currency

Select your language and currency preferences for the site. Please note that all transactions will be processed in USD

Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Key West Vacation Rentals

1 - 42 of 310 rentals
  PrevNext  
Sun 24 Jun Mon 25 Jun Tue 26 Jun Wed 27 Jun Thu 28 Jun Fri 29 Jun Sat 30 Jun Sun 1 Jul Mon 2 Jul Tue 3 Jul Wed 4 Jul Thu 5 Jul Fri 6 Jul Sat 7 Jul Sun 8 Jul Mon 9 Jul Tue 10 Jul
Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
215 231 225 226 225 258 258 256 266 270 270 232 - - - - -
Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
 Sunshine Drive - Key West, FL Vacation Rental

Sunshine Drive

Key West, FL
3 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 116 - - - 146 153 - - - 167 176 145 139 138
Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
- - - 281 - - - - - - - - - - - - -
Shark Key Chateau - Key West, FL Vacation Rental

Shark Key Chateau

Key West, FL
5 Bed 4.5 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
- - - 143 - - - 173 180 - - - - - - 154 -
Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
- - - - - - - 530 594 575 - - - - 469 - -
Tropical Hideaway - Key West, FL Vacation Rental

Tropical Hideaway

Key West, FL
2 Bed 1 Bath Sleeps 6
- - 221 - - - - - - - - - - - - - -
 Modern Rendezvous  - Key West, FL Vacation Rental

Modern Rendezvous

Key West, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - 931 1046 1015 1010
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
- 148 143 144 143 173 174 172 181 175 - - - 150 162 155 154
Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
0 Bed 1 Bath Sleeps 2
- 148 143 144 143 173 174 172 181 185 185 145 176 176 145 139 138
Royal Poinciana - Key West, FL Vacation Rental

Royal Poinciana

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 116 - - - - - - - - 167 176 145 139 138
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - 238 - - - - - - 233 248 250
Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - - - - 166 - - 172 - - - - - - 154 -
Casa Caribe @ Duval Square - Key West, FL Vacation Rental

Casa Caribe @ Duval Square

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- 285 277 263 - - - - - - - - - - - - -
Cabana Retreat - Key West, FL Vacation Rental

Cabana Retreat

Key West, FL
3 Bed 3 Bath Sleeps 8
- 206 201 201 200 224 224 211 226 223 232 210 221 216 195 196 197
Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
- 211 203 204 202 215 215 218 240 236 248 216 232 225 210 210 210
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
- - 136 - - - - - - - 175 - - - - - -
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- 217 209 - - - - - - - 238 234 277 269 234 236 237
Casa Bonita @ Duval Square R1 - Key West, FL Vacation Rental
- - 267 283 266 - - - 293 290 - - - - 251 - -
 Conch Cottage - Key West, FL Vacation Rental

Conch Cottage

Key West, FL
1 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Duval Corner - Key West, FL Vacation Rental

Duval Corner

Key West, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - 164 - - - - - - - -
Tsalta - Key West, FL Vacation Rental

Tsalta

Key West, FL
3 Bed 3 Bath Sleeps 8
- 252 243 244 242 262 263 245 267 262 274 243 258 251 230 233 235
Duval Dreamin' - Key West, FL Vacation Rental

Duval Dreamin'

Key West, FL
2 Bed 2 Bath Sleeps 6
105 105 105 105 105 170 171 135 147 144 151 134 143 139 111 111 111
Casa Atlantic - Key West, FL Vacation Rental

Casa Atlantic

Key West, FL
3 Bed 3 Bath Sleeps 9
- - - - 170 205 206 191 208 204 214 190 202 196 171 172 173
Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - 378 - - - - 422 - - - - - - 391
Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

Key West, FL
1 Bed 1 Bath Sleeps 4
113 115 113 113 112 129 129 128 133 135 135 122 130 130 125 121 120
Bermuda Suite - Key West, FL Vacation Rental

Bermuda Suite

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

Waterfall 4

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - 124 - - - - - - -
Canalside in the Keys - Key West, FL Vacation Rental

Canalside in the Keys

Key West, FL
2 Bed 2 Bath Sleeps 6
162 166 160 161 160 191 191 189 198 203 203 179 193 194 180 173 172
Papa's Hideaway #1 - Torrents of Spring - Key West, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - 118 118
Saint Thomas Suite #302 - Key West, FL Vacation Rental

Saint Thomas Suite #302

Key West, FL
2 Bed 2 Bath Sleeps 6
159 - - - 158 - - - - - - - - - - - -
Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Martinique Suite #108 - Key West, FL Vacation Rental

Martinique Suite #108

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - 167 - -
Cristobal Suite #411 - Key West, FL Vacation Rental

Cristobal Suite #411

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Caribbean Dreams - Key West, FL Vacation Rental

Caribbean Dreams

Key West, FL
0 Bed 1 Bath Sleeps 2
- 129 125 125 118 - - - - - - 138 176 176 145 139 138
Cozumel Suite #112 - Key West, FL Vacation Rental

Cozumel Suite #112

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - 181 - - - - - - - 168 -
Page 1 of 8

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

  • Searching ...
  • 42 of 310
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here