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Private pool
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Swimming pool

Heated pool
Private indoor pool
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Cot available
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Swing set or jungle gym
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Staffed property
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Parking
Car not required

Children under 5
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Smoking - Ask
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City breaks
Skiing – property near ski resort
Walking trips
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Golf within 30mins drive
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62 house rentals

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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

Match: Swing set or jungle gym Private pool

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Price per night from

$544

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$573

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$481

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$556

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$476

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$320

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$285

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$286

Pirates Paradise

Cudjoe Key house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$433

Lobster Lagoon

Stock Island house

4 bedrooms
4 bathrooms

sleeps 9

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$973

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$315

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$1,718

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$478

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

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: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$840

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$134

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$382

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$515

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!

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$573

Harbor Walk Hideaways

Key West b&b

4 bedrooms
3 bathrooms

sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$1,300

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$790

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$621

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: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$2,119