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Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Cot available
Sea view
Safe
Dishwasher
Children's pool
Pool or snooker table
Table tennis
Games room
Clothes dryer
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Fax machine
Climbing frame
Video player
Freezer
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Microwave
Boat available
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Staffed property
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
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
Water sports
Fishing
Cycling trips
Waterfront
Golf within 30mins drive

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48 apartments in Cudjoe Key with pools

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Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

Match: Swimming pool

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Price per night from

$790

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

Match: Swimming pool

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Price per night from

$753

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

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$476

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$573

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$258

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.

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Price per night from

$602

Cuddie Cottage: 2BR Waterfront Home in Venture Out Resort, Open Water Views, Sha

Cudjoe Key house

2 bedrooms
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$160

Tropical Treasures - Beautiful Canal Front Home On Cudjoe Key With Quick Open Wa

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$182

Pirates Paradise

Cudjoe Key house

3 bedrooms
4 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$433

Breezy Palms: Exquisite Open Water Keys Paradise W/ Spectacular Views, Dockage,

Cudjoe Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

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Price per night from

$179

Blue Dolphin: Waterfront Bliss, Dock Your Boat, Enjoy Community Pool/Hot Tub, Te

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

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Price per night from

$179

Great rentals within 20 miles that match your search

Real World MTV House Key West 18 to 22 GUESTS

Key West house

10 bedrooms
6 bathrooms

sleeps 22

Match: Swimming pool

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Price per night from

$2,518

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Match: Swimming pool

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Price per night from

$1,946

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

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

Match: Swimming pool

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Price per night from

$307

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$556

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$378

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

Match: Swimming pool

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Price per night from

$1,718

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$252

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

Match: Swimming pool

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Price per night from

$320

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$285

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

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

Match: Swimming pool

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Price per night from

$800

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$286

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Swimming pool

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Price per night from

$695

Blackbeard's Escape

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$358

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

4 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$409

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

Match: Swimming pool

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Price per night from

$401

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$343

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms
5 bathrooms

sleeps 20

Match: Swimming pool

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Price per night from

$801

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!!!

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Price per night from

$287