Vacation Rentals & House Rentals in Key West

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45 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. 59 minutes

Match: Climbing frame Water sports

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Price per night from

$545

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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: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$134

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$339

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$689

Sweet Caroline Seaport Key West Home Rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$314

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$488

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$345

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$108

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$481

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$259

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$230

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$517

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$178

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$379

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$231

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$184

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$4,016

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$384

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$201

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$976

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Water sports

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 38 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$206

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: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$517

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$347

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$1,148

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$345

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$396

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: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$431

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$623

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$488

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$1,950

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$801

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$263

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$230

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: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$107

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$1,303

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: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$342

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Water sports

1 of 2 filters match

Price per night from

$912

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