Vacation Rentals & House Rentals in Florida Keys

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103 house rentals

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Housekeeping Included

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Price per night from

$912

Responds fast! avg. 3 hours 34 minutes

Match: Boat available Housekeeping Included

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Price per night from

$1,606

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Boat available Housekeeping Included

All filters match

Price per night from

$4,014

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Housekeeping Included

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Price per night from

$316

Match: Boat available Housekeeping Included

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Price per night from

$263

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Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$442

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 2 match: Housekeeping Included, Boat available

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Price per night from

$430

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$401

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$458

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$174

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$144

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$114

Cabanas Key Largo Unit 3

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 15 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$172

The Real Livaboard Experiance. Cruise Inciuded!

Key Largo yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$687

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$402

“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$316

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Boat available

1 of 2 filters match

Price per night from

$327

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$316

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$281

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$281

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$281

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$281

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$281

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$774

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Housekeeping Included

1 of 2 filters match

Price per night from

$975

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