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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.

  • 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!”

  • 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!!!”

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

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

Other great holiday rentals in Islamorada

Live-Laugh-Love  In Islamorada
SUPERHOSTPrivate room
Live-Laugh-Love In Islamorada
Price:£126 / night
Bayside hideaway
Entire house
Bayside hideaway
Price:£64 / night
Capt Craigs Guest Quarters
Remodeled 1/1 Apartment
SUPERHOSTEntire flat
Capt Craigs Guest Quarters Remodeled 1/1 Apartment
Price:£85 / night
Oceanfront, Private Beach, Beach Cottage w/Kayaks
SUPERHOSTEntire house
Oceanfront, Private Beach, Beach Cottage w/Kayaks
Price:£304 / night
Garden apartment in unique setting
Entire flat
Garden apartment in unique setting
Price:£121 / night
Ocean Islamorada BeachHouse wavail Boat & 70' DOCK
SUPERHOSTEntire townhouse
Ocean Islamorada BeachHouse wavail Boat & 70' DOCK
Price:£105 / night
Fla.KeysB&B+Brkfast.HomTaverner1-6ppl/1-30nite
Entire loft
Fla.KeysB&B+Brkfast.HomTaverner1-6ppl/1-30nite
Price:£80 / night
The Island Dog Conch House 2 Bedoom Islamorada FL
SUPERHOSTEntire villa
The Island Dog Conch House 2 Bedoom Islamorada FL
Price:£109 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
NEW Secret Keys Waterfront Hideout has EVERYTHING!
Price:£242 / night
Great weekend gateway
Entire guest house
Great weekend gateway
Price:£73 / night
Enjoy the Floirda Keys
SUPERHOSTEntire apartment
Enjoy the Floirda Keys
Price:£109 / night
Tiny Hm Elegant Camping/Glamping.Cabin.Pvt.Bath
Tiny house
Tiny Hm Elegant Camping/Glamping.Cabin.Pvt.Bath
Price:£95 / night
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