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Cudjoe Key Rentals with Pools

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age 0-16
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32 apartments in Cudjoe Key with pools

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$683

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$687

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!

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$524

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

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$569

$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

Responds fast! avg. 3 hours 27 minutes

Match: Swimming pool

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Price per night from

$172

Peaceful and Ocean View Estate 15 minutes from Key West

Cudjoe Key house

4 bedrooms / 2 bathrooms / sleeps 12

“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.

Match: Swimming pool

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Price per night from

$484

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

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$182

Great rentals within 20 miles that match your search

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 37 minutes

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Price per night from

$186

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$330

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

Little Torch Key house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$243

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$467

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

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Price per night from

$2,156

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$258

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$1,707

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,250

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$341

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

$552

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$217

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

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!!!

Responds fast! avg. 1 hour 35 minutes

Match: Swimming pool

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Price per night from

$256

NEW! Charming 'Boho Breeze' Retreat w/ Pool Access

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$142

Barry Beach - Waterfront Beach House with Dock & Heated Pool!

Little Torch Key house

8 bedrooms / 5 bathrooms / sleeps 20

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Price per night from

$632

Coral Breeze by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$119

Cottage by the Pool By At Home in Key West

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$112

A Little Slice of Paradise by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$112

Coral Villa by AT HOME IN KEY WEST

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$130

Bye Bye Birdie - Spacious 3 bedroom Golf Club Living

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$148

Bogey's Retreat by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$112

CORAL GARDEN Away from it all By At Home in Key West

Stock Island townhouse

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$119

Wind Swept by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$119

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Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$487

New Listing! Summerland Canal-Front Escape w/ Private Pool & Boat Basin

Summerland Key house

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$119

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