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Vacation Rentals in Key West, FL

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$198
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Studio, 1 Bathroom, Sleeps 4
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Also consider
Garden Home Paradise in Midtown Key West
2 Bedrooms, sleeps 6
$600 / night
Easy Livin - Villa in Truman Annex Key West
3 Bedrooms, sleeps 8
$571 - $1,029 / night
It's a Sweet Deal in Historic Old Town
1 Bedroom, sleeps 4
$139 - $228 / night
Southernmost Retreat- 1 Block from Duval
3 Bedrooms, sleeps 6
$288 - $600 / night
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$233
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1 Bedroom, 1 Bathroom, Sleeps 4
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$199
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$199
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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$219
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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$408
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$138
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Studio, 1 Bathroom, Sleeps 4
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Studio, 1 Bathroom, Sleeps 2
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Studio, 1 Bathroom, Sleeps 4
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$348
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$368
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$178
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1 Bedroom, 1 Bathroom, Sleeps 4
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$275
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$268
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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$239
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$138
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Studio, 1 Bathroom, Sleeps 4
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Studio, 1 Bathroom, Sleeps 4
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$248
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Studio, 1 Bathroom, Sleeps 2
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Studio, 1 Bathroom, Sleeps 2
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$188
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1 Bedroom, 2 Bathrooms, Sleeps 4
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$268
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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$225
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$1,195
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$158
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Studio, 1 Bathroom, Sleeps 2
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$198
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Studio, 1 Bathroom, Sleeps 2
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$298
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$188
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Studio, 1 Bathroom, Sleeps 2
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$1,195
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$188
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Studio, 1 Bathroom, Sleeps 4
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$188
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Studio, 1 Bathroom, Sleeps 4
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$318
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$4,500
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2 Bedrooms, 3 Bathrooms, Sleeps 4
26 photos Details
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$250
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$258
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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$208
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$408
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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$248
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability

  • Wheelchair access (22)
  • Elder access (107)
  • Suitable for children (75)
  • Pet friendly (122)
  • Smoking allowed (4)

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  • Air Conditioning (369)
  • Other outdoor space (335)
  • Internet (328)
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Book Online(224)

Suitability

  • Wheelchair access (22)
  • Elder access (107)
  • Suitable for children (75)
  • Pet friendly (122)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (369)
  • Other outdoor space (335)
  • Internet (328)
  • All pools (269)
  • Grill (229)
  • View all amenities
Key West Vacation Rentals

Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

Where to rent in Key West, Florida

Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Key West Bars and Restaurants

Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Sightseeing and Activities in Key West

Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.