Key West Vacation Rentals

(78 rentals)
A Touch Of Cuba In Key West

A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

$271

per night

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Villa Serena Duval Square

Villa Serena Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

2 BR | 2 BA | Sleeps 6 | Quick View

$211

per night

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Colony Sunset Suite

Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

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Ann Street Tranquility

Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

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The Duval Compound

The Duval Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

$1250

per night

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Conch Cottage

Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

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Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

Studio | 1 BA | Sleeps 2 | Quick View

1

$152

per night

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My Condo by the Beach with Ocean View

$169

per night

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Bougainvillea Villa Key West-monthly rental on water with private pool & dock

Bougainvillea Villa Key West-monthly rental on water with private pool & dock

3 BR | 2 BA | Sleeps 6 | Quick View

1

$167

per night

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SUNSET KEY, Villa Ambriana, LUXURY UPSCALE HOME RIGHT ON THE BEACH, 30 day stay

$399

per night

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Superb Location, Affordably Priced - The TwoSim Suite

Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

$135

per night

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Southard Street - Queen Conch

Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

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Casa de Cuba

Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

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Brass Palm Villa -Private Luxury Key West Home with Heated Pool

$643

per night

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"Southard Comfort"

"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

1

$157

per night

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Palm Villa

Palm Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$471

per night

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Dos Casas - 2 Houses 2 blocks from Duval in beautiful Old Town -- Monthly Rental

$193

per night

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Peaceful 2 BR Condo with All Amenities *** Free shuttle service ***

Peaceful 2 BR Condo with All Amenities *** Free shuttle service ***

2 BR | 2 BA | Sleeps 6 | Quick View

$171

per night

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Private beach estate,gated,dock,and pool

$857

per night

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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow.

$193

per night

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Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

$117

per night

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Duval Square Penthouse

Duval Square Penthouse

4 BR | 4 BA | Sleeps 8 | Quick View

$575

per night

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Historic Studio on the Waterfront at the Red Doors

$100

per night

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Pete's Cottages

Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

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6 BR, 5.5 BA Luxury Key West Beach House in Old Town at Fort Zachary Taylor

6 BR, 5.5 BA Luxury Key West Beach House in Old Town at Fort Zachary Taylor

6 BR | 5.5 BA | Sleeps 10 | Quick View

$1929

per night

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Luxury Shark Key waterfront home with beach 10 minutes from downtown Key West

$253

per night

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Casa Atlantica One Bedroom

Casa Atlantica One Bedroom

1 BR | 1 BA | Sleeps 2 | Quick View

$201

per night

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Duval Square Courtyard Condo

Duval Square Courtyard Condo

3 BR | 2 BA | Sleeps 6 | Quick View

$400

per night

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Artist's House Duval Square

Artist's House Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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2 BR, 2 BA Oceanfront Oasis On The Beach in Key West

$714

per night

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Namaste

Namaste

1 BR | 2 BA | Sleeps 2 | Quick View

$260

per night

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Duval Square Retreat

Duval Square Retreat

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

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2 BR, 1 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR, 1 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR | 1 BA | Sleeps 4 | Quick View

$393

per night

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Beach Club #204

Beach Club #204

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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Sea Watch 2 BR Open Water Luxury Penthouse - Ask About Our Specials!

Sea Watch 2 BR Open Water Luxury Penthouse - Ask About Our Specials!

2 BR | 2 BA | Sleeps 6 | Quick View

$500

per night

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4 BR, 3 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR, 3 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR | 3 BA | Sleeps 8 | Quick View

$697

per night

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Coconut Cabana

Coconut Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$425

per night

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Pete's East Cottage

Pete's East Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$233

per night

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CasaBella Duval Square

CasaBella Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$300

per night

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Vista Fresco

Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

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Casa Atlantica Studio

Casa Atlantica Studio

Studio | 1 BA | Sleeps 2 | Quick View

$200

per night

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Sea Watch 3 BR Open Water Luxury Penthouse - Ask About Our Specials!

Sea Watch 3 BR Open Water Luxury Penthouse - Ask About Our Specials!

3 BR | 3 BA | Sleeps 7 | Quick View

$714

per night

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La Brisa #403E Ocean Vista

La Brisa #403E Ocean Vista

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

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Colony Poolside

Colony Poolside

1 BR | 1 BA | Sleeps 2 | Quick View

$200

per night

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3 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

3 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

3 BR | 2 BA | Sleeps 6 | Quick View

$633

per night

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A Touch of Paradise.. pool, close to beach & Duvall. 2 FULL baths, 7 night Min.

A Touch of Paradise.. pool, close to beach & Duvall. 2 FULL baths, 7 night Min.

2 BR | 2 BA | Sleeps 5 | Quick View

$242

per night

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Ann Street Cottage

Ann Street Cottage

1 BR | 1 BA | Sleeps 2 | Quick View

$237

per night

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Louisa's Hideaway

Louisa's Hideaway

3 BR | 3 BA | Sleeps 6 | Quick View

$551

per night

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Louisa House

Louisa House

4 BR | 3 BA | Sleeps 8 | Quick View

$551

per night

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Local Weather

 | 

75°  65°
JANUARY
Ocean 71°
76°  66°
FEBRUARY
Ocean 71°
79°  69°
MARCH
Ocean 73°
82°  72°
APRIL
Ocean 78°
85°  76°
MAY
Ocean 81°
88°  79°
JUNE
Ocean 83°
89°  80°
JULY
Ocean 85°
90°  79°
AUGUST
Ocean 87°
88°  79°
SEPTEMBER
Ocean 85°
85°  76°
OCTOBER
Ocean 83°
81°  72°
NOVEMBER
Ocean 78°
77°  67°
DECEMBER
Ocean 75°

Stay steps from the sand in your Key West vacation rental

Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere.

From a romantic bungalow for a couple to a house that can fit your entire family and more, the Key West house rentals are endless. When staying in one of our Key West vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our condos and villas even come with special amenities like a set of bicycles, chef’s kitchen, and in-home theater. Use the filters to narrow down your choices and choose the property that calls to you, just like Key West does.

Key West, Florida travel advice

Thanks to economic boom and a bustling cigar industry, this area's became quite a hot spot by the turn of the 20th century. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.

Climate

Abundant sunshine and gentle breezes make Key West one of the most popular tourist destinations in Florida. With over 320 sunny days per year you’ll most likely get the weather you want, no matter when you visit. Be sure to bring plenty of sunscreen and beach umbrellas as the UV rays can be quite strong here. The sea temperature is almost bath water and you’ll love the turquoise-blue color.

Top activities and attractions

Even getting to Key West is an adventure. The Overseas Highway is one of the most beautiful drives in the country. Completed in 1938, it connects a string of cays and coral rock with 113 miles of concrete roadway. The aptly named Seven Mile Bridge is the longest and most scenic of the entire route.

Key West’s diverse and unique ecosystems are a result of the convergence of two major bodies of water. There’s endless entertainment to be had on the ocean. You’ve got the deep blue Atlantic and its Gulf Stream current to the south and the shallow flats of the Gulf of Mexico to the west. From deep sea fishing to parasailing and even just body surfing, you’ll love a day out on the water in Key West.

Hop on the Conch Tour Train for a fun way to see the surrounding area. You’ll get a narration of the city’s past from an experienced tour guide as you cruise around the streets. Walking tours are one of the best ways to see the city, too. Peek in at the area’s intriguing architecture, courtyards, and gardens.

On the presidential side of life, don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset.

Dining and Nightlife

Over 300 restaurants and bars make this city one of the most fun places to be in southern Florida. For those with a sophisticated palate, try the highly-rated Bien restaurant to indulge in Latin & Cuban flavors. For great sandwiches and service, eat at the cleverly named Munch Box to break up your day of adventure. For Korean food that will make you scream “WOW”, pop in to Garbo’s Lunchbox. And lastly, for those who love to brunch, visit Key Plaza Creperie for delicious breakfast foods.

At night, Duval Street is the place to be. The Green Parrot is Key West’s oldest bar but it’s still a rockin’ atmosphere. Famed local Ernest Hemingway loved to get sauced at Sloppy Joe’s bar. (Don’t miss the Ernest Hemingway Home & Museum to get a closer look at what made this famous author tick.) For those who like the legitimate arts, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse.

For the kids, take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views.

Key West vacation homes on FloridaRentals.com

Vacation rentals in Key West on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!