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Key West Vacation Rentals

1 - 42 of 307 rentals
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Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
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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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 Modern Rendezvous  - Key West, FL Vacation Rental

Modern Rendezvous

Key West, FL
2 Bed 2 Bath Sleeps 4
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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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Truman @ Duval - One Bedroom - Key West, FL Vacation Rental
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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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Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
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Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

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

Passover Cottage

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
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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
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Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
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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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Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
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Caribbean Dreams - Key West, FL Vacation Rental

Caribbean Dreams

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

Shipyard Perch

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

Tsalta

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

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
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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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Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
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Truman @ Duval - Studio - Key West, FL Vacation Rental

Truman @ Duval - Studio

Key West, FL
0 Bed 1 Bath Sleeps 2
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Commodore's Cove - Key West, FL Vacation Rental

Commodore's Cove

Key West, FL
4 Bed 4 Bath Sleeps 12
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Banana Breeze @ Key Cove - Key West, FL Vacation Rental

Banana Breeze @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
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Whitehead Manor - Key West, FL Vacation Rental

Whitehead Manor

Key West, FL
5 Bed 2 Bath Sleeps 9
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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
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Nautical Wheeler  - Key West, FL Vacation Rental

Nautical Wheeler

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

Waterfall 4

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

Amelia House

Key West, FL
3 Bed 2 Bath Sleeps 8
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Audubon House - Key West, FL Vacation Rental

Audubon House

Key West, FL
1 Bed 2 Bath Sleeps 4
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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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Secret Garden - Key West, FL Vacation Rental

Secret Garden

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

Bahama House

Key West, FL
3 Bed 3 Bath Sleeps 8
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Casa Hueso - Key West, FL Vacation Rental

Casa Hueso

Key West, FL
4 Bed 3.5 Bath Sleeps 8
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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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Duval Quarters - Key West, FL Vacation Rental

Duval Quarters

Key West, FL
1 Bed 1 Bath Sleeps 4
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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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