Vacation Rentals & Apartments in Cudjoe Key

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75 apartments

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

Match: Housekeeping Included Jacuzzi or hot tub

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Price per night from

$2,290

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$4,015

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

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

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Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Housekeeping Included

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Price per night from

$114

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Jacuzzi or hot tub, Housekeeping Included

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Price per night from

$775

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Price per night from

$263

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Housekeeping Included

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Price per night from

$516

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Jacuzzi or hot tub, Housekeeping Included

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Price per night from

$1,475

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Housekeeping Included

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Price per night from

$446

Bahia Azul

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$269

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$178

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$660

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$401

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$1,432

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$573

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$859

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$1,432

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$458

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$1,088

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$630

$and D0llar$: 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: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$179

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: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$115

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$251

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: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$321

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: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$689

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$264

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$1,492

"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: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$984

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$308

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$640

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Jacuzzi or hot tub

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Price per night from

$1,369

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rentals in Cudjoe Key

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