Vacation Rentals & House Rentals in Key West

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

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$165

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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: Private outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$487

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$481

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$911

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: Private outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$344

Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$458

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$840

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$478

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,119

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Somewhere on the Beach a dream property all amenities included simply amazing

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,432

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$745

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Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$974

Tranquility by Smathers and 10 minute bike downtown Key West value savings

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$802

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,718

Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,145

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$796

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,145

Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$573

Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$974

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$764

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,374

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$478

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,374

High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$974

Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$745

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$859

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,374

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