Vacation Rentals & House Rentals in Florida Keys

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39 house rentals

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Table tennis Golf course on site or within 15 min walk

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Price per night from

$620

Match: Table tennis Golf course on site or within 15 min walk

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Price per night from

$816

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Table tennis Golf course on site or within 15 min walk

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Price per night from

$652

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Table tennis Golf course on site or within 15 min walk

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Price per night from

$523

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

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$165

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$514

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$510

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$523

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$482

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$445

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$525

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$485

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$799

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$656

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$741

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$469

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$263

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$907

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$341

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$306

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$411

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

1 of 2 match: Table tennis, Golf course on site or within 15 min walk

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Price per night from

$343

Blue Moon Tavernier

Tavernier house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

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Price per night from

$400

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

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Price per night from

$80

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

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Price per night from

$770

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$1,483

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$229

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$513

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$514

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: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$172

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$571

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$223

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$336

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: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$1,141

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$1,084

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: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$797

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

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$542

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Table tennis

1 of 2 filters match

Price per night from

$314

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