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Key West Vacation Rentals

1 - 42 of 295 rentals
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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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Papa's Hideaway  - Garden of Eden - 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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Audubon House - Key West, FL Vacation Rental

Audubon House

Key West, FL
1 Bed 2 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
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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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Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Cabana Retreat - Key West, FL Vacation Rental

Cabana Retreat

Key West, FL
3 Bed 3 Bath Sleeps 6
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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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Casa Bonita @ Duval Square R1 - 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
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Coastal Comfort @ Key Cove - Key West, FL Vacation Rental

Coastal Comfort @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
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Bonaire Suite #210 - Key West, FL Vacation Rental

Bonaire Suite #210

Key West, FL
2 Bed 2 Bath Sleeps 6
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Carriage Courtyard  - Key West, FL Vacation Rental

Carriage Courtyard

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

Tropical Retreat

Key West, FL
3 Bed 3.5 Bath Sleeps 8
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Curry House Room 4 - Key West, FL Vacation Rental

Curry House Room 4

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

Heron Hideaway

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

Casa Hueso

Key West, FL
4 Bed 3.5 Bath Sleeps 8
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Duval Square Penthouse R19 - Key West, FL Vacation Rental

Duval Square Penthouse R19

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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Ellen's Casa - Key West, FL Vacation Rental

Ellen's Casa

Key West, FL
2 Bed 2 Bath Sleeps 6
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Duval Dreamin' - Key West, FL Vacation Rental

Duval Dreamin'

Key West, FL
2 Bed 2 Bath Sleeps 6
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United House - Key West, FL Vacation Rental

United House

Key West, FL
2 Bed 1.5 Bath Sleeps 6
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Fishtail Hideaway - Key West, FL Vacation Rental

Fishtail Hideaway

Key West, FL
1 Bed 2 Bath Sleeps 5
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Saint Thomas Suite #302 - Key West, FL Vacation Rental

Saint Thomas Suite #302

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

Key West Nest

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

Villa Azul

Key West, FL
3 Bed 3 Bath Sleeps 6
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Toon Hall - Tropical Village - Key West, FL Vacation Rental
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Caribbean Suite - Key West, FL Vacation Rental

Caribbean Suite

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

Paradise on Sunset Key

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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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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Tierra Bomba Suite #403 - Key West, FL Vacation Rental

Tierra Bomba Suite #403

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

Caribbean Fling

Key West, FL
2 Bed 1.5 Bath Sleeps 6
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Hemingway's Shadow - Key West, FL Vacation Rental

Hemingway's Shadow

Key West, FL
1 Bed 1 Bath Sleeps 2
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Hispaniola Suite #101 - Key West, FL Vacation Rental

Hispaniola Suite #101

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

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
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Grand Cayman Suite #309 - Key West, FL Vacation Rental

Grand Cayman Suite #309

Key West, FL
2 Bed 2 Bath Sleeps 6
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About Key West

Key West rated 4.8 out of 5 based on 665 reviews Key west, FL

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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