Vacation Rentals & House Rentals in Key West

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98 house rentals

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 2 hours 26 minutes

Match: Iron Swing set or jungle gym

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Price per night from

$602

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Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$268

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$230

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$206

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$1,150

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$386

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$386

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$430

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$134

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$449

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$230

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$494

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$333

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$202

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$345

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$229

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$489

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$920

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$107

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$329

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$794

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$624

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$108

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$2,069

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$1,149

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$1,149

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$321

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$518

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$482

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$259

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$459

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$156

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$173

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$4,024

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$259

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$690

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$575

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$518

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