Vacation Rentals & House Rentals in Key West

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327 house rentals

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 58 minutes

Match: Shared indoor pool Towels provided

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Price per night from

$345

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Glamping in the Florida Keys

Grassy Key caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$184

Manatee Bay

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$261

Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$1,145

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$153

Ocean view condo with balcony

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$315

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$394

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$218

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$114

Bayside Retreat. Pool, Boat and Beach

Key Largo house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“SPLENDID VACATION” I had the opportunity to stay here with my family in March. The house was spacious and the beach and pool were exactly what we wanted for a private family vacation. The house manager, Kevin, could not have been more accomodating in seeing that all of our vacation needs were taken care of. I could have sat on the porch and watched the sunset views forever. Watch for the manatees when you are there, they are a lifetime experience.

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$1,263

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$442

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$2,214

Windley Key, FL Keys

Islamorada caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$115

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$230

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$173

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$144

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$268

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$229

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$208

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$178

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$675

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$141

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$184

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$174

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$171

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$224

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$214

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$158

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$155

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$1,550

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Shared indoor pool, Towels provided

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: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$206

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$316

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: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$430

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$859

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: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$384

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: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$384

Cabanas Key Largo Unit 6

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Pleasant place to stay for a few days” We got off on a bad foot as the room had not been cleaned before our arrival at 4:30PM (we were told we could check in a 3PM). The management was very responsive however, and paid for a complementary dinner at a fun, nearby restaurant by way of apology. The room was well designed and comfortable, if not spacious; the kitchenette and living/bedroom are all in one layout. It was fine for 2 guests but there would be no privacy if there were more. The cabana is right on the canals; boats pass frequently but it's not noisy. This was our first visit to the Florida Keys, and this cabana was a comfortable base for seeing Key Largo. It's not as convenient if you want to go as far south as Key West.

Responds fast! avg. 2 hours 15 minutes

1 of 2 match: Shared indoor pool, Towels provided

1 of 2 filters match

Price per night from

$172

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