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Key West Rentals

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Results: 1 - 30 of 586 Rentals

  • Old Town
    $850 - 1,029

    per night (USD)

    By: HomeAway

    Old Town

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Please call 772-291-7837 The Captain's House was built in 1870 by the Chavez Family and is listed on the National Regist ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $315 - 525

    per night (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This wonderful property has brand new living and bedroom furniture in 2016, King bed in the master bedroom, 2 twins in t ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $315 - 525

    per night (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the ...

    Details
  • Second Floor Oceanfront Condo in Private Gated Community on the Beach
    $371 - 856

    per night (USD)

    By: HomeAway

    Second Floor Oceanfront Condo in Private Gated Community on the Beach...

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This freshly renovated oceanfront condo has been meticulously designed and furnished to a very high standard. No expense ...

    Details
  • Oceanview Dual-house 2-acre Gated Estate With Accommodations For Up To 14 Guests
    $4,200

    per week (USD)

    By: HomeAway

    Oceanview Dual-house 2-acre Gated Estate With Accommodations For Up To 14 Guests

    Bedrooms:
    6
    Bathrooms:
    3
    Sleeps:
    14

    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an sp ...

    Details
  • 3 Bedrooms 3 Baths Sleeps 8
    $3,630 - 9,420

    per month (USD)

    By: HomeAway

    3 Bedrooms, 3 Baths, Sleeps 8

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Located just minuets from Duval St in a quiet mid-town neighborhood this attached 2 story house has everything you could ...

    Details
  • Luxurious 3BR 2BA Home + Steps From Smathers Beach 29 night minimum stay
    $1,372 - 3,577

    per week (USD)

    By: HomeAway

    Luxurious 3BR/2BA Home + Steps From Smathers Beach / 29 night minimum stay***

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    On a quiet residential street in the “Beachside” neighborhood is a very special home, designed to be your own private oa ...

    Details
  • Studio 0 Bedrooms 1 Baths 2 Sleeps
    $45

    per night (USD)

    By: HomeAway

    Studio, 0 Bedrooms, 1 Baths, 2 Sleeps

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    I am so happy you are reading this! Please feel free to call me directly to make payment on this condo. I take payment ...

    Details
  • Condo 1 Bedrooms 1 Baths 4 Sleeps
    $1,050 - 1,897

    per week (USD)

    By: HomeAway

    Condo, 1 Bedrooms, 1 Baths, 4 Sleeps

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and ...

    Details
  • Cozy studio nicely decorated close to the action yet far enough for relaxation
    $75

    per night (USD)

    By: HomeAway

    Cozy studio, nicely decorated, close to the action yet far enough for relaxation

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This studios sleeps 2 guests.complete with linens, flat screen TV, cable, Wi-Fi and kitchenette. This unit is perfect ...

    Details
  • Newly Decorated And Fully Appointed With Water View 30 NIGHT MIN STAY REQUIRED
    $22,770

    per month (USD)

    By: HomeAway

    Newly Decorated And Fully Appointed With Water View *30 NIGHT MIN STAY REQUIRED*

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    "Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...

    Details
  • VILLA AZUL Two bed two bath pet friendly condo in Old Town with Pool
    $3,465

    per week (USD)

    By: HomeAway

    "VILLA AZUL" ~ Two bed, two bath, pet friendly condo in Old Town with Pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    COMFORT AND VALUE IN OLD TOWN…. This second floor two bedroom condo is located in The Shipyard, a Truman Annex neighborh ...

    Details
  • Sophistication for perfectionists not vailable for less than one month rental
    $32,970

    per month (USD)

    By: HomeAway

    Sophistication for perfectionists, not vailable for less than one month rental

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Pristine renovation completed in 2016, never before on the rental market. In the heart of Old Town on a quiet street. T ...

    Details
  • In the epicenter of Key West and walking distance to everything in Old Town
    $19,770

    per month (USD)

    By: HomeAway

    In the epicenter of Key West and walking distance to everything in Old Town

    Bedrooms:
    5
    Bathrooms:
    3
    Sleeps:
    10

    HEMINGWAY’S HIDEAWAY Steps away from Hemingway’s house sits his “Hideaway”. Allow the authentic feel of old Key West ins ...

    Details
  • 1 Bedroom 1 Bathroom Sleeps 4
    $4,500

    per month (USD)

    By: HomeAway

    1 Bedroom, 1 Bathroom, Sleeps 4

    Bedrooms:
    0
    Bathrooms:
    1
    Sleeps:
    4

    This lively island cottage in the heart of Old Town. Short walks to Duval Street, Blue Heaven, Southernmost Point, Wine ...

    Details
  • Oceanfront 3BR 2BA Coastal Condo with views of the Atlantic Ocean
    $491 - 2,093

    per night (USD)

    By: HomeAway

    Oceanfront 3BR/2BA Coastal Condo with views of the Atlantic Ocean...

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    A stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully e ...

    Details
  • Studio 1 Bath Sleeps 2
    $108 - 212

    per night (USD)

    By: HomeAway

    Studio, 1 Bath, Sleeps 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old T ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $228 - 362

    per night (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between t ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 4
    $4,290 - 9,750

    per month (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    ***Due to city restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from res ...

    Details
  • 2 Bedrooms 2 5 Baths Sleeps 4
    $1,624 - 2,800

    per week (USD)

    By: HomeAway

    2 Bedrooms, 2.5 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    In one of the most desirable locations in Key West, you will find the exquisite Mangrove Lagoon. Just walking into this ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 4
    $3,120 - 6,480

    per month (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This property requires a minimum stay of 28 nights. Salt Pond Penthouse is the place to be if you are looking to relax ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $3,120 - 8,250

    per month (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you w ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $4,170 - 13,200

    per month (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome home. Literally. This secluded two bedroom home will feel like your very own! Conveniently located off of Cather ...

    Details
  • 4 Bedroom 3 Bathroom Sleeps 8
    $26,370

    per month (USD)

    By: HomeAway

    4 Bedroom, 3 Bathroom, Sleeps 8

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to 906 South Street, a beautiful Casa Marina Estate home located blocks away from the beach. Walk or bike to the ...

    Details
  • Florida Keys Getaway - Summerland Key United States
    $10,230

    per month (CAD)

    By: HomeAway

    Florida Keys Getaway - Summerland Key, United States

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Located on South Airport Drive in Summerland Key, Florida... Approximately 25 miles north of Key West 25 miles south of ...

    Details
  • 9 Bedrooms 9 Baths Sleeps 18
    $1,498 - 2,676

    per night (USD)

    By: HomeAway

    9 Bedrooms, 9 Baths, Sleeps 18

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the ...

    Details
  • 2 Bedroom 1 Bathroom with Vaulted Ceilings and Extra Large Balcony
    $155

    per night (USD)

    By: HomeAway

    2 Bedroom, 1 Bathroom with Vaulted Ceilings and Extra Large Balcony

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Hi there! We have just renovated our entire home and know you'll thoroughly enjoy yourself here. Welcome to your home ...

    Details
  • Private 3BR 3 5BA Home In Casa East District + Pool 29 night minimum stay
    $1,428 - 3,850

    per week (USD)

    By: HomeAway

    Private 3BR/3.5BA Home In Casa East District + Pool / 29 night minimum stay***

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Enjoy "Isla Momentos" warm charm in beautiful Key West. Isla Momentos (translated: Island Moments or Island Time) is l ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $315 - 525

    per night (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spectacular 2 bedroom 2 bath ocean-view overlooking the famous Smathers Beach, Enjoy the balmy ocean breezes from your ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $270 - 450

    per night (USD)

    By: HomeAway

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    1st floor garden-view unit, King in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the liv ...

    Details
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