Vacation Rentals & Apartments in Cudjoe Key

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147 apartments

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$391

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$641

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swimming pool

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Price per night from

$158

Expertly Decorated-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$576

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$636

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$1,329

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Staffed property Swimming pool

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Price per night from

$1,795

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$641

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Staffed property Swimming pool

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Price per night from

$1,795

Family Friendly w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$576

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$580

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$580

Roof Top Water Views - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$641

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$636

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Staffed property Swimming pool

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Price per night from

$580

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: Staffed property Swimming pool

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Price per night from

$2,290

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$431

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$286

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swimming pool

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Price per night from

$523

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Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$205

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Swimming pool, Staffed property

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Price per night from

$573

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Swimming pool, Staffed property

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Price per night from

$4,008

1 of 2 match: Swimming pool, Staffed property

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Price per night from

$263

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$377

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$343

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$363

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$286

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$819

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$358

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$212

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Swimming pool

1 of 2 filters match

Price per night from

$1,140

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$344

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Swimming pool

1 of 2 filters match

Price per night from

$524

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$229

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Swimming pool

1 of 2 filters match

Price per night from

$206

8c, Efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$229

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Swimming pool

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Price per night from

$252

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Swimming pool

1 of 2 filters match

Price per night from

$556

Viewing 38 of 147
rentals in Cudjoe Key

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