Vacation Rentals & Villas in Conch Key

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141 Houses

“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.

Price per night from

$327

Price per night from

$561

Great rentals within 20 miles that match your search

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

Price per night from

$409

Price per night from

$1,090

BAYSIDE Villa

Islamorada villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$316

Private studio with dock. Perfect getaway for fishing and grilling.

Marathon Shores studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$172

Price per night from

$1,320

Oceanside, Pet Friendly, Smart Home with-SUP, kayak with and 60 ft Dock

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$259

Glamping in the Florida Keys

Grassy Key caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$184

Price per night from

$821

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$155

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$574

Price per night from

$912

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$745

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$349

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$213

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,148

The Mini Coconut

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$259

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

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$343

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

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$308

Last Minute Sunday to Sunday Availability August 22nd - August 29th

Marathon Shores house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$517

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$373

Oceanside waterfront 2/2 home with 55ft dock and paddle equipment

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$287

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$572

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$251

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

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,472

Pet Friendly Half-Duplex, Cottage with 40' Slip Option at The Boat House Marina

Marathon Shores cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$195

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

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$516

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

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$344

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$602

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$286

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$377

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

Key Colony Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

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

Key Colony Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$217

Price per night from

$819

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$413

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$391

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$315

Viewing 38 of 141
rentals in Conch Key

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