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Key West Vacation Rentals

1 - 42 of 66 rentals
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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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Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - - 280 280 - - 265 - - - - 320
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - 250 260 260 260 260 260 260 260 260 260 260
Duval Hideaway: Cigar Maker's Cottage - Key West, FL Vacation Rental
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White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
295 295 295 295 315 315 315 270 270 270 270 255 - - - - -
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
99 99 99 99 115 99 - - - - - - - - - - -
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
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The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - 270 330 330 330 320 - - - - - - - 320 285
Perfect Boater's Retreat - Key Largo, FL Vacation Rental

Perfect Boater's Retreat

Key Largo, FL
3 Bed 2 Bath Sleeps 6
90 90 90 90 99 99 99 99 99 99 99 99 99 99 99 99 90
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 140 150 140 - - - - -
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - 165 175 175 150
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - - 230 - - - - - - 245 - - - -
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
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Fisherman's Canal Getaway - Key Colony Beach, FL Vacation Rental
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Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
195 220 220 220 220 - - - - - - - - - - - -
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
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Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - 185 - - - - - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
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Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
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White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - 190 195 195 195 195
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
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Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
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Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
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Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
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Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
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Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
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Fantastic Fifth Street - Key Colony Beach, FL Vacation Rental

Fantastic Fifth Street

Key Colony Beach, FL
4 Bed 2.5 Bath Sleeps 10
- - - 140 160 160 155 - - - - - - - - - -
Eleventh Street Legacy - Key Colony Beach, FL Vacation Rental
- - - - - - 155 - - - - - - - - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
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Comfort in the Keys - Key Colony Beach, FL Vacation Rental
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Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
- - - - - - 180 190 190 160 - - - - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 125 - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
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Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - 165 175 175 175 175 175 165 - -
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
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Fisherman's Dream Pad - Key Largo, FL Vacation Rental

Fisherman's Dream Pad

Key Largo, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - 136 136 136 136 136 136 136 136 136 136
Bright as Beach Sand - Key Colony Beach, FL Vacation Rental
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Tavernier Waterfront Retreat - Islamorada, FL Vacation Rental
140 - - - - - - - - - - - - - - 145 -
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About Key West

Key West rated 4.9 out of 5 based on 34 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, Florida? 

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 to 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, Florida

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 night life 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, Florida

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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