Vacation Rentals & House Rentals in Florida Keys

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287 house rentals

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: $133 Ceiling Fans

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Price per night from

$107

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: $133 Ceiling Fans

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Price per night from

$114

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: $133 Ceiling Fans

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Price per night from

$81

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

Match: $133 Ceiling Fans

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Price per night from

$107

Beautiful Private Home with Beach Access

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

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$86

Unique Houseboat on Dry Lot

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

Match: $133 Ceiling Fans

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Price per night from

$98

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Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$1,145

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$153

Ocean view condo with balcony

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$315

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 38 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$393

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$218

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$144

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$315

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$441

Bayside Retreat. Pool, Boat and Beach

Key Largo house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“SPLENDID VACATION” I had the opportunity to stay here with my family in March. The house was spacious and the beach and pool were exactly what we wanted for a private family vacation. The house manager, Kevin, could not have been more accomodating in seeing that all of our vacation needs were taken care of. I could have sat on the porch and watched the sunset views forever. Watch for the manatees when you are there, they are a lifetime experience.

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Price per night from

$1,260

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$172

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$140

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$267

Motel Room #2, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$212

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Price per night from

$228

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 1 match: Ceiling Fans

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Price per night from

$338

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$207

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$177

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$213

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$173

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$170

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 1 match: Ceiling Fans

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Price per night from

$224

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$183

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$157

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 1 match: Ceiling Fans

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Price per night from

$155

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 1 match: Ceiling Fans

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Price per night from

$1,546

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$229

Beautiful Beachfront Home w/Heated Pool+45' Dock

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!

1 of 1 match: Ceiling Fans

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Price per night from

$801

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$430

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 1 match: Ceiling Fans

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Price per night from

$430

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 1 match: Ceiling Fans

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Price per night from

$1,145

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$1,432

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 1 match: Ceiling Fans

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Price per night from

$859

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rentals in Florida Keys

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