Vacation Rentals & House Rentals in Florida Keys

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34 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: Private outdoor pool (unheated) Pool or snooker table

All filters match

Price per night from

$545

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Blue Moon Tavernier

Tavernier house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$401

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$771

FALL IN LOVE with your home away from home!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$206

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$908

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$486

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$205

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$389

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$223

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$158

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$1,142

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$379

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$655

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$523

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$623

Sunset Water Views! Moon Bay Key Largo Remodeled Condo with Boat Slip!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$316

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pool or snooker table

1 of 2 filters match

Price per night from

$396

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,203

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$971

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$514

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$314

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$400

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: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,297

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$457

$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: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$257

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$685

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: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$514

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$699

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,855

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

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,855

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$500

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$246

1 of 2 match: Pool or snooker table, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,998

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