Vacation Rentals & House Rentals in Florida Keys

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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: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,950

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

1 of 2 match: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$345

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: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$574

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,549

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,664

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$496

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$445

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$654

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$471

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$622

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$484

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$525

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$523

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$252

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$363

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

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

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$659

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

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$659

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

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$203

1 of 2 match: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Luxury Vacation Rental Oceanfront in Key Largo, nr, Islamorada, Florida Keys

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$206

Waterfront luxury Villa (19) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Private fishing lake or river, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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