Vacation Rentals & House Rentals in Florida Keys

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275 house rentals

BREATHTAKING Ocean views await at Tropical Daze

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 17 minutes

Match: Ceiling Fans Climbing frame

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Price per night from

$286

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

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Price per night from

$545

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Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, 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 2 match: Climbing frame, 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 2 match: Climbing frame, Ceiling Fans

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Price per night from

$316

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: Ceiling Fans, Climbing frame

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Price per night from

$206

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$394

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$218

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$114

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$316

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.

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$1,262

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$442

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$268

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$141

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 2 match: Climbing frame, Ceiling Fans

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Price per night from

$213

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$229

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: Climbing frame, Ceiling Fans

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Price per night from

$339

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$208

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$178

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$214

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$158

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$155

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$171

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$174

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$224

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$184

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

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$144

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$1,548

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$172

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$230

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 2 match: Climbing frame, Ceiling Fans

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Price per night from

$802

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: Climbing frame, 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 2 match: Climbing frame, Ceiling Fans

1 of 2 filters match

Price per night from

$1,145

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$401

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Climbing frame, Ceiling Fans

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Climbing frame, Ceiling Fans

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Price per night from

$859

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Climbing frame, Ceiling Fans

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Climbing frame, Ceiling Fans

1 of 2 filters match

Price per night from

$630

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