Vacation Rentals & House Rentals in Florida Keys

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342 house rentals

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Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$247

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$1,751

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$1,751

$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

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$258

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$2,004

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!

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$1,300

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$500

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: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$602

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$458

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$401

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$700

$and D0llar$: 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

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$179

Casa Paraiso: Discover This Charming 2BR Canal Front Duplex in KCB with Private

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$182

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$134

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

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$168

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel,

Big Pine Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$179

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

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$516

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$687

Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$247

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$462

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

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

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$179

Reel 'Em In: Your Beautiful KCB Retreat, Private Pool, Dock, Tiki Hut, Cabana Cl

Key Colony Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$172

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

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Price per night from

$458

Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas

Stock Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$180

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapi

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$296

Responds fast! avg. 2 hours 34 minutes

Match: Clothes dryer Private outdoor pool (unheated)

All 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

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$180

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

Match: Clothes dryer Private outdoor pool (unheated)

All filters match

Price per night from

$179

Viewing 38 of 342
rentals in Florida Keys

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