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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Fax machine
Pool or snooker table
Table tennis
Games room
Shared outdoor pool (heated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Video player
Bicycles available
Boat available
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Staffed property
Microwave
Linen provided
Towels provided
Climbing frame
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Smoking allowed
Pets
Pets allowed
Parking

Car not required
Children under 5
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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41 house rentals

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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

Match: Private outdoor pool (heated) Smoking allowed

All filters match

Price per night from

$2,123

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$482

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$479

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

Key West apartment

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$841

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$459

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

Private, heated pool. Private yard.

Key West condo

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$803

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$746

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Smoking allowed, 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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,434

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,148

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$861

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, 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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,148

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$479

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,721

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$766

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$976

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$574

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

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Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$976

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,377

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Key West house

1 bedroom
1 bathroom

sleeps 4

“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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$798

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: Smoking allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$861

Historic Carriage House

Key West cottage

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Private outdoor pool (heated), Smoking allowed

1 of 2 filters match

Price per night from

$230

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Private outdoor pool (heated), Smoking allowed

1 of 2 filters match

Price per night from

$108

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms
1 bathroom

sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Private outdoor pool (heated), Smoking allowed

1 of 2 filters match

Price per night from

$134

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), Smoking allowed

1 of 2 filters match

Price per night from

$345