Vacation Rentals & Apartments in Cudjoe Key

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149 apartments

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool Wheelchair accessible

All filters match

Price per night from

$229

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool Wheelchair accessible

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Price per night from

$654

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool Wheelchair accessible

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Price per night from

$373

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

Match: Swimming pool Wheelchair accessible

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Price per night from

$253

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool Wheelchair accessible

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Price per night from

$802

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.

Match: Swimming pool Wheelchair accessible

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Price per night from

$487

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AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Swimming pool, Wheelchair accessible

1 of 2 filters match

Price per night from

$390

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swimming pool, Wheelchair accessible

1 of 2 filters match

Price per night from

$315

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swimming pool, Wheelchair accessible

1 of 2 filters match

Price per night from

$377

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$205

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

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: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$343

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$363

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$286

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$819

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$358

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$524

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$212

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, 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: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$344

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$206

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$481

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

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$556

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$567

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$773

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: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$573

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

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$307

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$476

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$184

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: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$217

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$285

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Wheelchair accessible, 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: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$286

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$911

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$433

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$602

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$409

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair accessible, Swimming pool

1 of 2 filters match

Price per night from

$1,145

Viewing 38 of 149
rentals in Cudjoe Key

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