Key West Vacation Rentals

(54 rentals)
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Studio | 1 BA | Sleeps 3 | Quick View

5

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

$425

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

New lower rates July/August call from 1pm-9pm - sooner is better chance.. ++++++++++++ Ask for more Ocean in your eyes! Call soon credit card Holds dates in your name ++++++++++++ Please happy easygoing persons shall love it here.. ty! This is Key West Beach Front Rental Welcome to; Ocean ...

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Property Type

Key West Studio

"Amazing place to stay- spectacular view"

This was our second time staying at here and we love it! The views and sound of the ocean are amazing! Place is clean and cozy. Host Holly is fantastic! We will definitely be returning again next year. ...

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2 BR | 2 BA | Sleeps 7 | Quick View

1

$133

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

"Awesome Key West Getaway-We'll be back!"

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$321

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

[PLEASE ASK ABOUT MY LATE SUMMER SPECIAL PRICE. Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, ...

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Property Type

Key West Condo

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

SUGARFOOT Looking for a SUMMER GETAWAY for remote work or fun?! LAST MIN DEAL ON JUNE. Call for discount pricing./1854531?unitId=2417040**#SUGARFOOT_SUNSETS** ENJOY PRIVATE BEACH, BRING YOUR BOAT A TRUE SUNSET FACING OASIS with incomparable view, Perfect remote workspace with high speed Wifi ...

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Property Type

Key West House

"Perfect Vacation Home for our big dogs and us!"

A perfect vacation home for us and our 2 big boxer dogs. The yard was completely fenced in where our large dogs could have a lot of space to run yet not be where our cars would park. They could be with ...

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Key West Vacation Rentals

Key West Weather

 | 

7524°  6518°
JANUARY
Ocean 7122°
7624°  6619°
FEBRUARY
Ocean 7122°
7926°  6921°
MARCH
Ocean 7323°
8228°  7222°
APRIL
Ocean 7825°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8329°
8932°  8027°
JULY
Ocean 8530°
9032°  7926°
AUGUST
Ocean 8731°
8831°  7926°
SEPTEMBER
Ocean 8530°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7826°
7725°  6719°
DECEMBER
Ocean 7524°

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 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!