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Vacation Rentals & House Rentals in Florida Keys

24 house rentals

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$184

New Rental Sombero Beach

Marathon Shores house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$857

Real World MTV House Key West

Key West house

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 10 bedrooms
  • 6 bathrooms
  • sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Price per night from

$1,805

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

  • Beach / lakeside relaxation
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$149

THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

Islamorada condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$163

100' Private Beach Front Ocean Front Estate

Islamorada house

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,145

Dolphin Oasis 4bdr/4bth Pool/hot tub 115' dockage

Marathon house

  • Nearest beach 4 mi
  • •  Swimming pool
  • •  Child Friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic house, in excellent location and managed directly by the super-efficient and friendly owner!” This house is ideally situated in Marathon - halfway between Key Largo and Key West. Easily accessible with great local amenities. There is ample comfortable accommodation inside and fantastic outdoor facilities including a large pool and hot tub and various seating areas and fire pit. We could even watch a manatee swimming at the dockside of the house! Craig (the owner) made contact with us soon after we arrived and made every effort to ensure that our holiday was the way we wanted it to be - he could not have been more friendly or accommodating.

Price per night from

$425

PARADISE IN KEY LARGO Townhouse

Key Largo townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$207

Extraordinary waterfront custom home

Marathon Shores house

  • Child Friendly
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$739

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)

Key West house

  • Swimming pool
  • •  Ski
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$716

Family vacation rental, kayak, pool, 50” dock

Key Largo house

  • Nearest beach 0.02 mi
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$173

Welcome to Paradise

Long Key townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Price per night from

$205

Escape to Paradise

Key Largo house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Fabulous!!” We booked this beautiful house for our first week in the Keys. We had a group of adults and kids who went down for the week and we took our boat. This beautiful house had plenty of space for all of us and a ton of outside space to enjoy. The access to the water was easy on both the Gulf and Atlantic side. The amenities provided with the house or perfect. There was actually more than we usually find in a rental house. We had a few minor issues with the house that were taken care of very promptly by the owner. We will definitely be back next year.

Price per night from

$241

Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)

Islamorada condo

  • Child Friendly
  • •  Pet Friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$111

Seaside Condo 2 pools JANUARY SPECIAL

Key West condo

  • Beach / lakeside relaxation
  • •  Nearest beach 0.3 mi
  • •  Swimming pool
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$100

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$176

UNFORGETTABLE FAMILY GETAWAY! MARVELOUS 2BR/2BA VILLA, 5 POOLS, TENNIS COURTS

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$427

New Listing! Spacious 3BR/2BA Family Villa, 5 Pools, Tennis, Spa, Private Beach

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$583

New Listing! Incredible 2BR/2BA Family Villa, 5 Pools, Tennis, Spa, Beach

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$427

FANTASTIC FAMILY GETAWAY! LOVELY 2BR/2BA VILLA IN SUNSET VILLAGE, 5 POOLS/TENNIS

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$427

RARE FIND! FANTASTIC 3BR/2BA FAMILY VILLA FOR 8 GUESTS, 5 POOLS, TENNIS, SPA

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$583

Oceanfront Islamorada Condo with Huge T-Dock

Islamorada condo

  • Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$153

ULTIMATE FAMILY GETAWAY! LOVELY 3BR/2BA VILLA FOR 8, 5 POOLS, TENNIS!

Duck Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$583

2 Bedroom, 2 Bath Condo with Kitchen, Living Room, Balcony, Pool, Parking,WiFi

Key West condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$248

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