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Vacation Rentals in Key West Area

Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!

Vacation Rentals in Key West Area

Maison du Calais

  • 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • Maison du Calais – Old Town Amenities: Heated Pool, Deck, Jacuzzi, Washer/Dryer, Dishwasher, DVD Player, High Speed Internet, Separate cottage…
  • from
  • $5000
    monthly

 

Lost Weekend

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Lost Weekend – Old Town is perfectly situated for the discriminating guest who wants to enjoy Key West at its…
  • from
  • $4500
    monthly

 

Elgin Hideaway

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Elgin Hideaway – Old Town Enjoy this beautiful 2 story historic home, sunny pool, large open floor plan for entertaining…
  • from
  • $4000
    monthly

 

Casita Mango

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Casita Mango – Old Town Casita Mango is a lovely retreat for your Key West stay, whether for one or…
  • from
  • $2750
    monthly

 

Yellow on White

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Yellow on White – Old Town Yellow on White is conveniently located next to a full spa to relax your…
  • from
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  • 0 Bedroom, 0 Bathroom, Sleeps 0
  • from
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Windsor Townhome #1

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Windsor Townhomes – Old Town Elegance and modern sophistication are apparent as you enter any one of these six newly…
  • from
  • $458
    nightly

 

Secret Courtyard Cottage

  • 2 Bedrooms, 1 Bathroom, Sleeps 5
  • Secret Courtyard Cottage -Old Town Welcome to a little piece of hidden paradise you never knew existed. Once you’re nestled…
  • from
  • $275
    nightly

 

Bella Vita

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Bella Vita – Old Town Located half a block from infamous Duval St, this beautiful 1 bedroom, one bathroom property…
  • from
  • $188
    nightly

 

Paradise Harbor Retreat

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Paradise Harbor Retreat – Old Town This gorgeous four level home is a luxurious waterfront property. It is a spacious…
  • from
  • $550
    nightly

 

La Brisa #304W Egrets Landing

  • 0 Bedroom, 2.5 Bathrooms, Sleeps 5
  • Property Description 30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating.…
  • from
  • $3131
    weekly

 

Red on White

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Red on White – Old Town Located in the heart of the White Street art district, just six blocks from…
  • from
  • $128
    nightly

 

Purple on White

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Purple on White – Old Town Located on White street just six blocks from both Duval Street and the Historic…
  • from
  • $128
    nightly

 

Green on White

  • 1 Bedroom, 1 Bathroom, Sleeps 3
  • Green on White– Old Town Green on White is located just six short blocks from both Duval street and the…
  • from
  • $128
    nightly

 

Blue on White

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Blue on White– Old Town Blue on White is located in the heart of the White Street art district, just…
  • from
  • $128
    nightly

 

Windsor Townhome #5

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…
  • from
  • $458
    nightly

 

Buena Vista

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Buena Vista – Old Town This wonderfully indulgent one bedroom cottage is on Center Street, just one-half block from Duval…
  • from
  • $178
    nightly

 

Windsor Townhome #3

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…
  • from
  • $458
    nightly

 

La Casa De Luces

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • La Casa De Luces – Old Town Come to relax or to play while enjoying the spectacular sunsets and the…
  • from
  • $168
    nightly

 

Heron Suite

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Heron Suite– Old Town Tucked among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Heron Suite.…
  • from
  • $188
    nightly

 

Royal Escape

  • 3 Bedrooms, 3 Bathrooms, Sleeps 10
  • Royal Escape – Old Town If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom,…
  • from
  • $458
    nightly

 

Cuban Club Suite

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Cuban Club Suite – Old Town Built in 1917 as a “club” for Cuban cigar makers and their families as…
  • from
  • $228
    nightly

 

Island Retreat in Key West

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Located behind a private gated community you will find our newly remodeled, comfortable, casual, private vacation home. Our home is…
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'PARADISE @ THE BIGHT': Large 5BR/4BA Waterfront Home w/Private Dock...

  • 5 Bedrooms, 4 Bathrooms, Sleeps 10
  • This beautiful 5 bedroom home is located directly on the water at Garrison Bight, with direct access to Florida Bay.…
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'PORTSIDE MANSION @ THE SEAPORT': 6BR 6.5BA Compound @ Historic…

  • 6 Bedrooms, 6 Bathrooms, Sleeps 12
  • In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and…
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"Colorful Conch"

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • If you are going to spend time in America's Tropical Paradise, why not make the most of it? This beautiful…
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"Roger's Retreat"

  • 4 Bedrooms, 2.5 Bathrooms, Sleeps 8
  • If you're going to spend time in America's Tropical Paradise, why not make the most of it? This beautiful private…
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"Heavenly Zen"

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully…
  • from
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"Casa Blanca 1888"

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This gracious home has everything you would want for your stay in Old Town Key West. Its central location in…
  • from
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"Maison Tropicale"

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Imagine a traditional conch home stunningly restored, then decorated in a post-modern style with vivid colors and sophisticated decor. Every…
  • from
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"Penthouse @ The Steamplant"

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • There is nothing else like this home in all of Key West: Card-only access to your assigned spaces in the…
  • from
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"Villa Bahama @ The Foundry"

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
  • This beautiful town home is to be found in the Truman Annex, Key West's most exclusive gated community. You'll be…
  • from
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"Tropical Jewel @ Elizabeth"

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • f ever a home was a precious jewel, it is this immaculate restoration located on 320 Elizabeth Street just two…
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"La Casita Amarilla @ The Meadows"

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • In the Meadows, a neighborhood with some of the nicest homes in town, this exquisitely detailed home on 1314 Petronia…
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"Gulfside Vistas @ The Annex"

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
  • This beautiful penthouse condo is the perfect place to spend your stay in Key West, with panoramic views of the…
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Windows on the Gulf @ The Annex

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
  • Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo in the Truman Annex is…
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Conch Casita 4 @ Elizabeth

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • You will never find this perfect little cottage (or its sister cottages, 'Conch Casita 1' and Conch Casita 2') without…
  • from
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Conch Casita 3 @ Elizabeth

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • You will never find this perfect little cottage (or its sister, "Conch Casita 2") without directions, even though it is…
  • from
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Conch Casita 2

  • 1.5 Bedrooms, 1 Bathroom, Sleeps 2
  • Private Cottage, 1.5 Bedrooms, 1 Bath, (Sleeps 2-3) This wonderful little cottage is the sister to "Conch Casita 3" and…
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"Sunset Dreams 2"

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • "Sunset Dreams 2" has everything you could want in a vacation home: it is very close to Old Town, so…
  • from
  • $3000
    monthly

 

Windsor Townhome #2

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…
  • from
  • $458
    nightly

 

Tortuga Hammock

  • 2 Bedrooms, 3 Bathrooms, Sleeps 4
  • Tortuga Hammock – Stock Island Not even 1 mile from Key West proper, this gem is hidden right off of…
  • from
  • $258
    nightly

 

La Casa Cubana

  • 1 Bedroom, 1.5 Bathrooms, Sleeps 6
  • La Casa Cubana – Old Town Sitting just steps around the corner from the infamous Duval Street, this spacious 1…
  • from
  • $188
    nightly

 

Orchid Suite

  • 1 Bedroom, 1 Bathroom, Sleeps 6
  • The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with…
  • from
  • $178
    nightly

 

Colors on White

  • 5 Bedrooms, 5 Bathrooms, Sleeps 17
  • Colors on White– Old Town Colors on White is located in the heart of the White Street art district, just…
  • from
  • $515
    nightly

 

Casa Loca

  • 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • Casa Loca – Old Town is perfect for the discriminating guest who wants to enjoy the finest Key West has…
  • from
  • $458
    nightly

 

Hidden Treasure

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Hidden Treasure – Old Town Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping,…
  • from
  • $258
    nightly

 

Island style

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Island Style– Old Town Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages,…
  • from
  • $188
    nightly

 

Casa Louisa

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Casa Louisa is a charming turn-of-the-century cigar cottage located in the center of the historic cigar-making district of old Key…
  • from
  • $400
    nightly

 

Andrews Inn Garden Cottage in Key West, Florida

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Savor the peace and quiet of your own sundeck or your own jacuzzi. You're sure to have a memorable vacation…
  • from
  • $160
    nightly

 

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