Vacation Rentals & Apartments in Cudjoe Key

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool Walking trips

All filters match

Price per night from

$355

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Swimming pool Walking trips

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Price per night from

$81

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool Walking trips

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Price per night from

$161

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 58 minutes

Match: Swimming pool Walking trips

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Price per night from

$320

the private and secluded PENINSULARHOUSE

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.

Match: Swimming pool Walking trips

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Price per night from

$400

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool Walking trips

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Price per night from

$500

These homes match some but not all of your filters. Clear all filters

1 of 2 match: Swimming pool, Walking trips

1 of 2 filters match

Price per night from

$561

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

1 of 2 match: Swimming pool, Walking trips

1 of 2 filters match

Price per night from

$327

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, Walking trips

1 of 2 filters match

Price per night from

$573

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swimming pool, Walking trips

1 of 2 filters match

Price per night from

$516

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

1 of 2 match: Swimming pool, Walking trips

1 of 2 filters match

Price per night from

$327

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Walking trips, 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: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$343

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, 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: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$286

1 of 2 match: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$358

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, 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: Walking trips, 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: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$206

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$252

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

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, 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: Walking trips, 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: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$307

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$556

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, 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: Walking trips, 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: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$217

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$320

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$285

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$286

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$433

1 of 2 match: Walking trips, Swimming pool

1 of 2 filters match

Price per night from

$911

Viewing 38 of 151
rentals in Cudjoe Key

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