Vacation Rentals & House Rentals in Florida Keys

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101 house rentals

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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: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$107

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,948

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

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: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$574

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$344

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,548

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,663

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Sunsets and Sand

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$149

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$364

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$373

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$253

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$660

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$660

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$203

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$641

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$581

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,191

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$640

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$581

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,371

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$581

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$641

Roof Top Water Views - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$759

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rentals in Florida Keys

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