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  
Wed 13 Jun Thu 14 Jun Fri 15 Jun Sat 16 Jun Sun 17 Jun Mon 18 Jun Tue 19 Jun Wed 20 Jun Thu 21 Jun Fri 22 Jun Sat 23 Jun Sun 24 Jun Mon 25 Jun Tue 26 Jun Wed 27 Jun Thu 28 Jun Fri 29 Jun
Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - 223 236 227 231 225 226 225 258
Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 137 148 143 144 143 173
 Modern Rendezvous  - Key West, FL Vacation Rental

Modern Rendezvous

Key West, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - 838 - - - - - - -
Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - - - - - - - - - - - - - - - 166
Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
- - - - - - - - - - - - - - 281 - -
Passover Cottage - Key West, FL Vacation Rental

Passover Cottage

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - 407 - - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - 116 - -
Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - 378 -
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Bahama House - Key West, FL Vacation Rental

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - 168 169 163 165 161 162 161 185
Paradise on Sunset Key - Key West, FL Vacation Rental

Paradise on Sunset Key

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

Cabana Retreat

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - 203 202 206 201 201 200 224
Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
- - - - - - - - - - 228 275 264 - - - -
 Sunshine Drive - Key West, FL Vacation Rental

Sunshine Drive

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

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Hibiscus Room - Key West, FL Vacation Rental

Hibiscus Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - 120 - 116 - -
Tropical Hideaway - Key West, FL Vacation Rental

Tropical Hideaway

Key West, FL
2 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - 221 - - -
Casa Key West @ Duval Square - Key West, FL Vacation Rental
- - - - - - - - - - - 402 434 422 399 - -
Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
- - - - - - - - - - - - - - 143 - -
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 117 - - - - -
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 - - -
Shark Key Chateau - Key West, FL Vacation Rental

Shark Key Chateau

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

Oceana Suite

Key West, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
- - - - - - - - - - 273 279 282 278 278 277 296
Tsalta - Key West, FL Vacation Rental

Tsalta

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - 250 246 252 243 244 242 262
Duval Dreamin' - Key West, FL Vacation Rental

Duval Dreamin'

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - 99 99 105 105 105 105 105 170
Spa On Duval @ Duval Square R11 - Key West, FL Vacation Rental
- - - - - - - - - - - - - 262 263 - -
Toon Hall - Tropical Village - Key West, FL Vacation Rental
- - - - - - - - - - - 351 - - - - -
Canalside in the Keys - Key West, FL Vacation Rental

Canalside in the Keys

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - 172 173 162 166 160 161 160 191
Flagler's Crossing - Key West, FL Vacation Rental

Flagler's Crossing

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - 151 152 151 154 150 150 149 167
Duval Quarters - Key West, FL Vacation Rental

Duval Quarters

Key West, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - 150 150 -
Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 137 148 143 144 143 173
Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

Key West, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - 117 118 113 115 113 113 112 129
Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 123 126 - - - -
Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 111 - - - 110 -
Cristobal Suite #411 - Key West, FL Vacation Rental

Cristobal Suite #411

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Rum Cay Suite #304 - Key West, FL Vacation Rental

Rum Cay Suite #304

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - 158 - - -
Waterfall 3 - Key West, FL Vacation Rental

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Bahama Dreaming - Key West, FL Vacation Rental

Bahama Dreaming

Key West, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - 474 - - - - -
Royal Poinciana - Key West, FL Vacation Rental

Royal Poinciana

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - 116 - -
Casa Del Sol - Key West, FL Vacation Rental

Casa Del Sol

Key West, FL
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
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