Vacation Rentals & House Rentals in Florida Keys

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100 house rentals

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Islamorada Ocean Views! Pool, Wi-Fi, Balcony, Gym, Covered Parking

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 44 minutes

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$802

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$573

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$344

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$573

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$621

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$790

Kokomo Cove Boat House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$400

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$670

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$344

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$165

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$556

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$567

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$659

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$982

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$801

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$332

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$287

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$573

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$307

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$481

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,145

1 of 2 match: Video player, Private outdoor pool (heated)

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Price per night from

$2,127

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: Video player, Private outdoor pool (heated)

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Price per night from

$801

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$201

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$802

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$378

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,718

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$476

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,088

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$285

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,317

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$800

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,472

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Video player, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$784

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