Vacation Rentals & House Rentals in Florida Keys

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277 house rentals

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Ceiling Fans Children's pool

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Price per night from

$344

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Ceiling Fans Children's pool

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Price per night from

$158

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Ceiling Fans Children's pool

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Price per night from

$567

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Ceiling Fans Children's pool

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Price per night from

$316

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BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Ceiling Fans, Children's pool

1 of 2 filters match

Price per night from

$253

Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$1,145

Ocean view condo with balcony

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$314

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$153

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 2 match: Children's pool, 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

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$218

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Ceiling Fans, Children's pool

1 of 2 filters match

Price per night from

$230

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$213

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$157

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$155

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Ceiling Fans

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Price per night from

$1,542

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Children's pool, Ceiling Fans

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Price per night from

$229

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. 2 hours 25 minutes

1 of 2 match: Children's pool, Ceiling Fans

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$114

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$315

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$172

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: Children's pool, Ceiling Fans

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Price per night from

$430

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$1,261

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$442

Motel Room #2, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$212

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

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 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$338

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$267

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$801

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$1,145

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$207

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$177

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$140

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$430

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: Children's pool, Ceiling Fans

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$573

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$1,088

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$1,432

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: Children's pool, Ceiling Fans

1 of 2 filters match

Price per night from

$630

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rentals in Florida Keys

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