Vacation Rentals & Apartments in Cudjoe Key

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Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Swimming pool Car not required

All filters match

Price per night from

$660

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool Car not required

All filters match

Price per night from

$345

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool Car not required

All filters match

Price per night from

$1,950

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

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Swimming pool Car not required

All filters match

Price per night from

$801

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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: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$206

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$378

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$821

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$359

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$213

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$524

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$363

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$1,140

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$343

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: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$344

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$286

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$482

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

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$557

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$308

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$775

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$476

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$286

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$320

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$287

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$912

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$434

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$1,148

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$614

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$410

New Listing! Charming Angler's Reef Home with Pool, Dockage

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$459

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$207

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$574

Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!

Key Colony Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$343

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$229

New Listing! Gone Coastal-Waterfront Bring Your Boat! Cabana Club Membership

Key Colony Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$217

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Car not required, 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: Car not required, Swimming pool

1 of 2 filters match

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: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$252

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Swimming pool

1 of 2 filters match

Price per night from

$602

Viewing 38 of 146
rentals in Cudjoe Key

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