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Key West Vacation Rentals

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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  - Garden of Eden - Key West, FL Vacation Rental
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Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
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Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - 133 - - 126 -
Hemingway's First Home - Key West, FL Vacation Rental

Hemingway's First Home

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

Bougainvillea

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

Key West Interlude

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

Waterfall 3

Key West, FL
0 Bed 1 Bath Sleeps 2
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Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
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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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Hibiscus Room - Key West, FL Vacation Rental

Hibiscus Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - 139 143 142 133 -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
- - - - - - - 162 164 - - - 187 192 191 189 167
Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
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Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
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Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
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Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
2 Bed 2 Bath Sleeps 6
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Garden of Roses - Key West, FL Vacation Rental

Garden of Roses

Key West, FL
3 Bed 2 Bath Sleeps 8
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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 #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
- - - - - - - - 156 - - - 167 173 172 161 -
Toon Hall - Tropical Village - Key West, FL Vacation Rental
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Duval Corner - Key West, FL Vacation Rental

Duval Corner

Key West, FL
1 Bed 1 Bath Sleeps 4
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - - - - - - - - - - - 167 173 162 - -
Margarita Suite #305 - Key West, FL Vacation Rental

Margarita Suite #305

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
- - - - 250 254 234 216 232 290 287 274 228 209 208 254 251
Casa Key West @ Duval Square - Key West, FL Vacation Rental
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Mangrove Lagoon - Key West, FL Vacation Rental

Mangrove Lagoon

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

Passover Cottage

Key West, FL
2 Bed 2 Bath Sleeps 6
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Bermuda Suite - Key West, FL Vacation Rental

Bermuda Suite

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

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
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Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
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Oceana Suite - Key West, FL Vacation Rental

Oceana Suite

Key West, FL
1 Bed 1 Bath Sleeps 4
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Great Egret Escape - Key West, FL Vacation Rental

Great Egret Escape

Key West, FL
2 Bed 2.5 Bath Sleeps 4
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Flagler's Crossing - Key West, FL Vacation Rental

Flagler's Crossing

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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 Paradise Escape #407 - Key West, FL Vacation Rental

Paradise Escape #407

Key West, FL
2 Bed 2 Bath Sleeps 6
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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 -
Bay Harbor View - Key West, FL Vacation Rental

Bay Harbor View

Key West, FL
5 Bed 3 Bath Sleeps 18
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Bonaire Suite #210 - Key West, FL Vacation Rental

Bonaire Suite #210

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - 167 166 165 - - - 164 161 152 - -
Royal Poinciana - Key West, FL Vacation Rental

Royal Poinciana

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - 126 - - - - - - - - - 126 -
Nautical Wheeler  - Key West, FL Vacation Rental

Nautical Wheeler

Key West, FL
4 Bed 3 Bath Sleeps 8
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Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
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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

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