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Cudjoe Key Rentals with Pools

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age 0-16
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36 apartments in Cudjoe Key with pools

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 18

Responds fast! avg. 1 hour 18 minutes

Match: Swimming pool

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Price per night from

$667

Paradise on Cudjoe Bay

Cudjoe Key house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Match: Swimming pool

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Price per night from

$350

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$662

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. 1 hour 18 minutes

Match: Swimming pool

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Price per night from

$484

Yellow weekly vacation home, great location. Heated private pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$403

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

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 22 minutes

Match: Swimming pool

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Price per night from

$542

Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests

Cudjoe Key house

6 bedrooms / 3 bathrooms / sleeps 14

“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

$489

Ocean Front Home-Private heated pool, gorgeous sunsets from gazaebo, boat dock

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 18 minutes

Match: Swimming pool

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Price per night from

$460

Great rentals within 20 miles that match your search

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$184

FLORIDA KEYS PARADISE! HEATED SWIMMING POOL

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$297

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Match: Swimming pool

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Price per night from

$342

Gone Fishing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$219

Come live the dream aboard BIG E NUFF

Stock Island boathouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 14 minutes

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Price per night from

$178

Canal Front Home with Seawall & Kayaks

Little Torch Key house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$252

Blue weekly vacation rental, great view. Heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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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

Responds fast! avg. 35 minutes

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Price per night from

$349

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“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. 3 hours 31 minutes

Match: Swimming pool

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Price per night from

$1,935

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 34 minutes

Match: Swimming pool

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Price per night from

$1,283

Blue Paradise- Oceanfront Townhouse close to Key West

Big Coppitt Key townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$174

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$219

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. 3 hours 26 minutes

Match: Swimming pool

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Price per night from

$288

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$413

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

Match: Swimming pool

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Price per night from

$1,265

Key West Living-Oceanside Catamaran "Spirit of the Wind"

Key West yacht

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$402

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Swimming pool

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Price per night from

$344

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$229

Oceanfront Oasis

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$333

Oceanfront Oasis

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$333

Oceanfront Oasis

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$391

Bogey's Retreat

Stock Island house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$74

Coral Breeze

Stock Island house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$74

Wind Swept

Stock Island house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$74

Coral Villa

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 6

“Coral Villa” This rental was perfect for my family. It was about 10-15 minutes from Duvall Street and Old Town Key West. The pool was a great place to relax. The only downside was the noise from the road right behind our rental, after the first night though we did not notice the noise anymore.

Match: Swimming pool

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Price per night from

$108

A Little Slice Of Paradise

Stock Island house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$74

4BR Home & 2BR Guest House w/ Private Boat Basin & Pool

Little Torch Key house

6 bedrooms / 4 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$393

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Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$453

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