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Key West, FL Vacation Rentals

Your search results for rentals in Key West:Page 1 of 20

'VILLA MODERNE @ VONPHISTER': 4BR/4BA Luxury Home with Pool by Beach...

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  • Spend your vacation in this lovely cottage in Key West where it's 5 o'clock all the time! This 4Br home is simply adorable and made for relaxing. Spend the day out shopping on the Blvd., sipping a cold one, or on the beach, which is just a couple of blocks away!

    Type: House
    Bedrooms: 4
    Sleeps: 8
    Bathrooms: 4/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $6600-14000

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'THE CORAL HOUSE @ THE SEAPORT': Lush 4BR/3.5BA Private Home w/Pool & Spa...

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  • Located in the heart of the historic old part of Key West, this gorgeous 4BR home is decorated in only the finest of everything. Great location for a relaxing vacation with exquisite furnishing and surrounded by all the history of an old seaport town. Live it, love it!

    Type: House
    Bedrooms: 4
    Sleeps: 10
    Bathrooms: 4/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $8000-16000

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“CASA PARADISO @ THE CLUB': Elegant 2BR/1.5BA Home near Community Pool......

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  • Sail away to paradise in Key West at this awesome 2BR, 2 story home located in a gated community. This home provides the ultimate setting for a relaxing vacation with porches and upstairs balcony. Also comes with access to golf course, pool and all the hospitality Key West has to offer!

    Type: Villa
    Bedrooms: 2
    Sleeps: 5
    Bathrooms: 1/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $2000-5000

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'AZURE MORNING' @ OCEANSIDE MARINA': Lavish 3BR/2BA Oceanfront Condo w/Pool

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  • You can't get any more tropical than this Condo located on the Ocean in Key West! This 3 BR Condo is comfortably furnished and offers the best in location with marina and airport only minutes away. Private balcony with ocean views will have you dreaming of never leaving!

    Type: Condo
    Bedrooms: 3
    Sleeps: 8
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $1600-2850
    Monthly: $5000-9900

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'SOUTHERNMOST BELLE @ THE ANNEX': Historic 7BR/5BA Home, Wide Porches & Pool

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  • This historical 7Br home in Key West has lots to offer and has been totally remodeled to include modern facilities. Wooden floors, high ceilings, wrap around porches, private pool and lots of room await you in this lovely home with lots of character located in most desirable area of Key West.

    Type: House
    Bedrooms: 7
    Sleeps: 14
    Bathrooms: 5/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $9000-13000
    Monthly: $30000-48000

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“FAT NANCY'S VILLA @ THE CLUB”: Bright & Airy 2BR/2BA Townhome near The Pool

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  • Type: House
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $2500-4800

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'WATER'S EDGE @ GULFVIEW POINTE': Waterfront 4BR/2.5BA Home, Private Pool...

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  • Type: House
    Bedrooms: 4
    Sleeps: 10
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $5500-12000

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'CONCH CASITA 3 @ ELIZABETH': Immaculate 2BR/1BA Conch Cottage in Old Town...

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  • Type: Cottage
    Bedrooms: 1
    Sleeps: 4
    Bathrooms: 0/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $2500-4800

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'BAMBOO RETREAT @ MILLS PLACE' Redecorated 2BR/2.5BA Villa in Truman Annex...

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  • Type: Cottage
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $2950-3950
    Monthly: $7700-13000

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Truman Annex Best Location it Town

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  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $1000-1800
    Monthly: $3000-5400

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'TROPICAL JEWEL @ ELIZABETH': 2BR/2BA Restored Conch Cottage @ The Seaport...

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  • Type: House
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $4000-10000

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'CONCH CASA GRANDE @ TRUMAN ANNEX': Grand 7BR/7BA Home, 6 Master Suites...

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  • Type: House
    Bedrooms: 7
    Sleeps: 12
    Bathrooms: 7/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $7700-16000
    Monthly: $28000-40000

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“AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo, Pool & Spa...

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  • Type: House
    Bedrooms: 3
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $1600-2850
    Monthly: $5000-9900

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“FALLING WATER @ THE SEAPORT': Luxury 5BR/4.5BA Compound, Pool & Hot Tub...

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  • Type: House
    Bedrooms: 5
    Sleeps: 10
    Bathrooms: 4/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $14000-22000

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'OLD TOWN OASIS @ TRUMAN ANNEX': Spacious 2BR/2BA Oceanfront Condo w/Pool

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  • Type: Condo
    Bedrooms: 2
    Sleeps: 5
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $1900-3600
    Monthly: $6000-12000

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'COLORFUL CONCH @ THE SANCTUARY': Immaculate 4BR/3BA Private Home, Pool...

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  • Type: House
    Bedrooms: 4
    Sleeps: 8
    Bathrooms: 3/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $5000-11000

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“WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA PenthouseCondo...

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  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:
    Weekly: $2700-4400
    Monthly: $8500-14000

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“THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool...

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  • Type: House
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $4400-8500

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'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Marina...

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  • Type: Condo
    Bedrooms: 3
    Sleeps: 6
    Bathrooms: 2/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $3300-7700

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'CIELO TROPICALE @ CASA EAST': 4BR/4BA Pavilion-Style Home with Pool..

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  • Type: House
    Bedrooms: 4
    Sleeps: 10
    Bathrooms: 4/0
    Town: Key West
    Zip Code: 33040

  • Rental Rates:

    Monthly: $8000-16000

    Check Availability

Looking for the perfect place to stay on your vacation in Key West, Florida? Browse our database of vacation rentals - including rental homes, condos, cottages, beach houses, and more!

Key West Vacation & Rental Tips

Amazing Vacation Rentals in Key West, FL

Nothing says Florida vacation better than Key West. When booking your next vacation rental, you couldn't pick a better destination to experience some of the best that Florida has to offer.

One of the most obvious but also one of the most enjoyable things to do is scuba diving. Whether you're an experienced diver or a beginner, Key West had a scuba diving program to accommodate you. To stay close to the action, book your vacation home near Roosevelt Boulevard and you'll be near Dive Key West Inc. Their team can teach you to dive or if you have experience in diving, they can take you on some amazing dives such as the one to the sunken Vandenberg, a former troop transport and missile tracking ship.

If food is your passion then you'll find the Margaritaville Cafe off of Duval Street, Salute Key West off of Atlantic Boulevard which is nestled right on the beach which features some great Italian cuisine or Turtle Kraals off of Margaret Street to satisfy your seafood craving. So as you can see, Key West can deliver whatever your palette is craving.

Of course you naturally cannot book your vacation rental in Key West and not try some of their world famous key lime pies. Drop by Kermit's Key West Key Lime Pie Shoppe off of Elizabeth Street and dive right in. Off of Greene Street you can stop by the Blond Giraffe and get some key lime pie on a stick.

For family fun, Key West has a lot to offer. Over off of College Road take the family to the Key West Tropical Forest and Botanical Gardens. Danger Charters located off of Cactus Drive wil take you on a wildlife tour that you won't forget.

Key West has so much to offer its visitors. So there is no time like the present to book your vacation rental.

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