Vacation Rentals & Apartments in Cudjoe Key

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68 apartments

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Jacuzzi or hot tub Car not required

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Price per night from

$661

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Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Car not required

1 of 2 filters match

Price per night from

$345

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Jacuzzi or hot tub, Car not required

1 of 2 filters match

Price per night from

$1,954

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

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Jacuzzi or hot tub, Car not required

1 of 2 filters match

Price per night from

$803

Bahia Azul

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$269

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$487

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,775

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,145

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$687

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$916

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,775

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$745

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$178

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$115

Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$252

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$81

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$288

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$489

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$391

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$340

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$794

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$624

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$489

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 33 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$986

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$321

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$518

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$690

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$265

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Car not required, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$986

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rentals in Cudjoe Key

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