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Vacation rentals in Islamorada

Vacation rentals in Islamorada

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Islamorada

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Capt Craigs Guest Quarters
Remodeled 1/1 Apartment
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Capt Craigs Guest Quarters Remodeled 1/1 Apartment

    Capt. Craig’s Guest Quarters The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

    What guests are saying:

    “I truly loved staying at Robert and Justin’s place. The interior was gorgeous and very clean. It was easy to find and his instructions were very helpful. We had one slight concern during our stay and they were quick to make it right and communicate effectively. I would recommend for anyone wanting to stay!”

  • FLAKEYS BED & BEER ****EXTRA CLEAN*****
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bath
    FLAKEYS BED & BEER ****EXTRA CLEAN*****

    Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

    What guests are saying:

    “Flakeys is a great spot- we've stayed in this apartment 3 times. It's very, very clean and comfortable and offers a central location in Islamorada. We have two young children and the layout is perfect. The fully equipped kitchen allows us to make as many meals as we'd like, and the balcony out back is a perfect spot after the kids are in bed. Because our kids are early risers, we aren't the night owls we once were and did notice the live music & noise from the beer garden behind the unit, but it usually dies down by 9 or 10. Cheryl is a great host, responds promptly, and offers great recommendations & local knowledge. If you're looking for a Keys getaway we strongly recommend Flakeys!”

  • Garden apartment in unique setting
    Entire apartment · 3 guests · 2 beds · 1 bath
    Garden apartment in unique setting

    Serene Islamorada pied à terre. Waterfront one-bedroom garden apartment in park like setting near natural reserve. Garden and water views from all rooms. Remodeled in 2019 with kitchenette, under counter fridge/freezer, drip coffee machines, microwave oven, and rice cooker, Casper bedding and big screen tv. Water access to launch paddles and kayaks. Ample parking and storage.

    What guests are saying:

    “Wonderful experience. The apartment was super clean and surprisingly large. Very cozy and perfect for my friend and I. The small beach view in the yard was a wonderful perk as well. Laurence was also very flexible and a great communicator. Would highly recommend this gem!”

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Islamorada vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Islamorada

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Conch Life Haven - Private-Parking - Fast Internet
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