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Vacation rentals in Islamorada

Vacation rentals in Islamorada

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Islamorada

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

  • Capt Craigs Guest Quarters
Remodeled 1/1 Apartment
    SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
    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 highly recommend staying at Robert’s place. What a beautiful, stylish, and convenient apartment in a wonderful location. Upon opening the door, we were happily surprised that it exceeded the pictures online. We will be staying here again (soon I hope)!! Thank you again Robert!!!”

  • Live-Laugh-Love  In Islamorada
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    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!”

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

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Popular amenities for Islamorada holiday rentals

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

Other great holiday rentals in Islamorada

Capt Craigs Guest Quarters
Remodeled 1/1 Apartment
SUPERHOSTEntire flat
Capt Craigs Guest Quarters Remodeled 1/1 Apartment
Price:₹7,878 / night
Live-Laugh-Love  In Islamorada
SUPERHOSTPrivate room
Live-Laugh-Love In Islamorada
Price:₹11,629 / night
Bayside hideaway
Entire house
Bayside hideaway
Price:₹5,927 / night
Oceanfront, Private Beach, Beach Cottage w/Kayaks
SUPERHOSTEntire house
Oceanfront, Private Beach, Beach Cottage w/Kayaks
Price:₹28,135 / night
Garden apartment in unique setting
Entire flat
Garden apartment in unique setting
Price:₹11,254 / night
1 King Ocean Front Kitchenette
Hotel room
1 King Ocean Front Kitchenette
Price:₹18,682 / night
Fla.KeysB&B+Brkfast.HomTaverner1-6ppl/1-30nite
Entire loft
Fla.KeysB&B+Brkfast.HomTaverner1-6ppl/1-30nite
Price:₹7,428 / night
The Island Dog Conch House 2 Bedoom Islamorada FL
SUPERHOSTEntire villa
The Island Dog Conch House 2 Bedoom Islamorada FL
Price:₹10,129 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
NEW Secret Keys Waterfront Hideout has EVERYTHING!
Price:₹22,433 / night
FLAKEYS BED & BEER ****EXTRA CLEAN*****
SUPERHOSTEntire house
FLAKEYS BED & BEER ****EXTRA CLEAN*****
Price:₹17,106 / night
Tiny Hm Elegant Camping/Glamping.Cabin.Pvt.Bath
Tiny house
Tiny Hm Elegant Camping/Glamping.Cabin.Pvt.Bath
Price:₹8,778 / night
Enjoy the Floirda Keys
SUPERHOSTEntire apartment
Enjoy the Floirda Keys
Price:₹10,129 / night
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