Key West Vacation Rentals

(36 rentals)
$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

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

$399

per night

View Details
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

View Details
The Duval Compound

The Duval Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

$1250

per night

View Details
Fabulous Gated Compound - Best Location in Old Town

Inquire for rates

View Details
Conch Cottage

Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

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

$643

per night

View Details
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

$159

per night

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

$117

per night

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

$193

per night

View Details
"Southard Comfort"

"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

1

$157

per night

View Details
Private beach estate,gated,dock,and pool

$857

per night

View Details
Palm Villa

Palm Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$471

per night

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

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

2 BR | 2 BA | Sleeps 4 | Quick View

$425

per night

View Details
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

View Details
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

View Details
Superb Location, Affordably Priced - The TwoSim Suite

Superb Location, Affordably Priced - The TwoSim Suite

0 BR | 1 BA | Sleeps 2 | Quick View

$135

per night

View Details
1 BR Margaritavilla Beach Cottage at Fort Zachary Taylor - Discounts Available!

1 BR Margaritavilla Beach Cottage at Fort Zachary Taylor - Discounts Available!

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

View Details
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

View Details
Key West 62" Motor Yacht In Private Luxury Resort Marina 3/2 - Family Friendly

$395

per night

View Details
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

View Details
A Touch of Bermuda at Truman Annex

$286

per night

View Details
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

View Details
Seaside Paradise monthly rentals- 2 pools, close to Old Town $1650 May-November

$77

per night

View Details
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

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

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

4 BR | 2 BA | Sleeps 8 | Quick View

$681

per night

View Details
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

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

$964

per night

View Details
Beach Studio Ocean views Key west Beach front rental!

Beach Studio Ocean views Key west Beach front rental!

0 BR | 1 BA | Sleeps 2 | Quick View

$229

per night

View Details
My Condo by the Beach with Ocean View

$169

per night

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

$253

per night

View Details
Key West Seashell Cottage - private home with spa, located on a quiet lane.

Key West Seashell Cottage - private home with spa, located on a quiet lane.

1 BR | 1 BA | Sleeps 2 | Quick View

$186

per night

View Details
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

View Details
Deluxe Key West Condo - Minimum 28 days Rental

$150

per night

View Details
Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

0 BR | 1 BA | Sleeps 2 | Quick View

1

$152

per night

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

$714

per night

View Details

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!