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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.

  • Oceanfront, Private Beach, Beach Cottage w/Kayaks
    SUPERHOSTEntire house · 6 guests · 3 beds · 2 baths
    Oceanfront, Private Beach, Beach Cottage w/Kayaks

    One of a kind home with a private beach, centrally located in a secluded area of the beautiful Island of Islamorada, surrounded by palms, pines, and lime trees, and a short distance to a great variety of restaurants. Perch on high above the Ocean in this charming 2 bed 2 bath beach cottage, with expansive Ocean views everywhere. Kayaks to fish/visit nearby islands right off the private beach are included.

    What guests are saying:

    “There aren’t enough words in the English dictionary to capture how much we love Gabriel’s home. It sits feet away from the crystal clear waters of the Florida Keys. Prior to coming I had only been to the Keys for quick trips and only in Key West. Islamorada will not disappoint. We found so many good restaurants to order from and also found the kitchen to be stocked with everything you need to make incredible dinners at home with our family. The views are epic... I think we must of taken 1000 plus pictures during our stay. There are views from every corner of the house. The beds are super comfy the house comes with everything you would need and we loved the welcome gift once we got here. There is no better place to spend some quality time with your friends and family. Gabriel is an incredible host, super responsive and accommodating to our questions and requests. I can’t wait to return.”

  • Live-Laugh-Love  In Islamorada
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Live-Laugh-Love In Islamorada

    The true “Live Aboard” experience on our 61 foot motor yacht. Islamorada is located in the upper keys, a truly beautiful Key with plenty of day and evening activities. Built in 2003, “Water Babes” is comfort and beauty in all of her teak glory. The fully equipped galley, lounging deck, and three sun decks are available for guest use. Located at our Marina is a huge gift shop, restaurant, fish market, paddle board rentals, kayak rentals and jet ski rentals; just walk down the dock.

    What guests are saying:

    “The yacht is spotless, and as a boater I know how difficult it is to maintain your craft. But Debbie goes the extra mile! She remembers the 2nd "B" in Airbnb, which is Breakfast. Each evening she would prepare for us the following: fresh fruit, Greek yogurt and a soy- and gluten-free protein bar. Along with their Keurig coffee maker, it started us off on the right foot because we visited the Keys' Historical & Discovery Center, toured Fort Zachary Taylor in Key West, as well as the Florida Keys' Wild Bird Rehab Center and the John Pennecamp Coral Reef State Park. But the highlight was dining on the beach at the Marker 88 Restaurant while the sun set. Thank you Debbie and Robert for that recommendation, and we already are looking forward to visiting you again next year!”

  • 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!”

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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

The Island Dog Conch House 2 Bedoom Islamorada FL
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The Island Dog Conch House 2 Bedoom Islamorada FL
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Capt Craigs Guest Quarters
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Capt Craigs Guest Quarters Remodeled 1/1 Apartment
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Garden apartment in unique setting
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Spring and Summer at Paradise
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Sunset Villas, 1-bedroom suite w/ Full Kitchen
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Sunset Villas, 1-bedroom suite w/ Full Kitchen
Price:€114 / night
Tropical Hideaway Hot Tub in Key Largo/Islamorada
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Tropical Hideaway Hot Tub in Key Largo/Islamorada
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Waterfront Ocean Side House with Dock & Boat Ramp
Entire house
Waterfront Ocean Side House with Dock & Boat Ramp
Price:€118 / night
Tropical Escape in Islamorada
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Tropical Escape in Islamorada
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A Piece Of Paradise, New Lic. Key Largo House 3/2
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A Piece Of Paradise, New Lic. Key Largo House 3/2
Price:€53 / night
Conch Life Haven - Private-Parking - Fast Internet
SUPERHOSTEntire guest suite
Conch Life Haven - Private-Parking - Fast Internet
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Awesome open Ocean view 2 bedroom at Ocean Pointe
SUPERHOSTEntire condominium
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Price:€172 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
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Price:€264 / night
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