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Key West Vacation Rentals

1 - 42 of 66 rentals
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Sunny Conch Getaway - Key West, FL Vacation Rental

Sunny Conch Getaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 190 190 190 190 190 195 195 195 195 195 195 195 195 195 195 195
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
280 - - - - 325 320 320 320 320 295 - - - - 275 275
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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Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - 245 255 255 255 255 255 255
Duval Hideaway: Cigar Maker's Cottage - Key West, FL Vacation Rental
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Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
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Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
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Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
- - - - 99 99 99 99 99 99 99 99 99 99 99 99 99
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
115 120 120 120 120 120 99 99 99 99 99 99 99 99 99 99 99
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
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The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
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White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
230 240 240 240 240 240 225 225 225 225 225 225 225 225 225 225 225
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - 165 - - - - - - 140 - - - -
Landings of Largo Gem - Key Largo, FL Vacation Rental

Landings of Largo Gem

Key Largo, FL
2 Bed 2 Bath Sleeps 7 (4 Adults Max)
65 70 70 70 70 - - - - - - - 70 65 65 65 65
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
- 155 165 165 140 - - - - - - - - - - - 155
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - 230 - - - 345 365 365 345 - - - - 345 365
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

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

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
195 215 215 215 250 250 195 195 195 195 195 195 - - - - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - 175 195 195 190 -
Sunnyside Canal  - Key Colony Beach, FL Vacation Rental

Sunnyside Canal

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 6
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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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Sunlit Serenity - Key Colony Beach, FL Vacation Rental

Sunlit Serenity

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
150 155 155 155 155 155 155 155 155 145 - - - - - - -
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
- - - - 135 145 145 145 145 145 145 125 - - - - -
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
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Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - 170 - - - - - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
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Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
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Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - - - - - - - 99 120 - - -
Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
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Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
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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
- - 295 320 275 - - - - - - - - - - - -
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - 130 - - - - - - - 130 140 140 130
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - 99 - - - - - - - 115 120 120 115
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
- 99 99 99 99 99 90 90 90 90 90 90 90 90 90 90 90
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- 165 165 165 165 165 155 - - - - - - - - - -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
150 155 155 155 155 155 155 155 155 155 155 155 155 145 - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - 145 155 155
Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
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Eleventh Street Legacy - Key Colony Beach, FL Vacation Rental
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White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
150 - - - - - - - 155 165 155 - - - - - -
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About Key West

Key West rated 4.9 out of 5 based on 42 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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