Vacation Rentals & House Rentals in Key West

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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: Fridge Swing set or jungle gym

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Price per night from

$544

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Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V

Sugarloaf Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$124

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$169

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

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, Fridge

1 of 2 filters match

Price per night from

$268

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: Swing set or jungle gym, Fridge

1 of 2 filters match

Price per night from

$339

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$178

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$184

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, Fridge

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, Fridge

1 of 2 filters match

Price per night from

$206

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

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: Swing set or jungle gym, Fridge

1 of 2 filters match

Price per night from

$384

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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, Fridge

1 of 2 filters match

Price per night from

$384

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, Fridge

1 of 2 filters match

Price per night from

$430

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Do

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$172

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$144

Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple F

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$458

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$182

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock &

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$180

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$153

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

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

1 of 2 filters match

Price per night from

$179

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rentals in Key West

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