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Cudjoe Key Rentals with Pools

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29 apartments in Cudjoe Key with pools

$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

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 DOLPHIN - Waterfront Home, Dock Your Boat, Community Pool/Hot Tub, Tennis C

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$179

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

$180

Great rentals within 20 miles that match your search

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$328

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$284

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. 38 minutes

Match: Swimming pool

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Price per night from

$2,174

Private Pool with Atlantic Ocean View- 20 minutes away from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$596

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

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!!!

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Price per night from

$256

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$227

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

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$332

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

Little Torch Key house

8 bedrooms / 5 bathrooms / sleeps 20

Match: Swimming pool

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Price per night from

$633

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$479

Ocean View Estate with Private Pool 15 minutes from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

“Absolutely Perfect for Our Family of 11” We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn!

Match: Swimming pool

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Price per night from

$489

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 37 minutes

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Price per night from

$343

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$1,946

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Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$487

New Listing! KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Y

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$179

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

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

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

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 Palm 3 bedroom, 3 bathroom townhome at Coral Hammock

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$130

Bogey's Retreat by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$112

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

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

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