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Wireless Internet
Air conditioning
Swimming pool
Private pool

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

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
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
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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60 house rentals

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Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

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Price per night from

$321

Great rentals within 20 miles that match your search

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$622

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

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Price per night from

$2,124

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$345

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$574

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

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$308

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$482

Private, heated pool. Private yard.

Key West condo

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$173

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$379

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$477

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$253

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$286

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

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

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Price per night from

$801

Pirates Paradise

Cudjoe Key house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$434

Blackbeard's Escape

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$359

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$287

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$410

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 24 minutes

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Price per night from

$402

Lobster Lagoon

Stock Island house

4 bedrooms
4 bathrooms

sleeps 9

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Price per night from

$976

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$792

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

Key West house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$165

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!

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Price per night from

$573

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,718

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms
5 bathrooms

sleeps 20

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Price per night from

$801

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$556

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$1,432

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$859

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$382

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$859

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$859

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!~

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Price per night from

$796