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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.

  • 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!”

  • 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 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!”

  • The Island Dog Conch House 2 Bedoom Islamorada FL
    SUPERHOSTEntire villa · 5 guests · 3 beds · 1 bathroom
    The Island Dog Conch House 2 Bedoom Islamorada FL

    Private 2 Bedroom / 1 Bathroom Villa in Islamorada of the Florida Keys at MM 77 The Villa offers the following. -Full Kitchen W/New Stainless Steel Appliances (Pots, Pans, Plates, Silverware, Cups, Wine Glasses, Coffee, Toaster and more,) -3 Flat Screen Smart TV's & Wifi -Tommy Bahama Blankets, Towels & Pillows Couch with Pullout Twin Mattress Dining Room Table & High-top Bar Table Private community Boat Ramp with Private Ocean Channel. Private Parking available Boats/Trailer depending on size.

    What guests are saying:

    “Everything I expected we received. We had a wreck with one of our party so it killed our weekend but I loved the place. We had 4 men in a fishing party and I was concerned about only one shower but we staggered and it was fine. Hot water, oh yeah, had to dial it back some. Close to Robbie's and two of our party went there, said the food was fantastic. If you have two vehicles, you'll have to park behind each other but it really wasn't va problem. Brett answers your messages right away. The key code on door took a minute to figure out, I think we had to enter it twice fast but we got in. We didn't use the WiFi or pool, or TVs so I can't comment on those. This was my first time Airbnb renting, but if it all works this easy, I'll do it again.”

Holiday rentals for every style

Get the amount of space that is right for you.

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  • Unique stays

Popular amenities for Islamorada holiday rentals

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

Other great holiday rentals in Islamorada

Spring and Summer at Paradise
SUPERHOSTEntire villa
Spring and Summer at Paradise
Price:₹22,498 / night
Oceanfront, Private Beach, Beach Cottage w/Kayaks
SUPERHOSTEntire house
Oceanfront, Private Beach, Beach Cottage w/Kayaks
Price:₹28,123 / night
Garden apartment in unique setting
Entire flat
Garden apartment in unique setting
Price:₹11,249 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
NEW Secret Keys Waterfront Hideout has EVERYTHING!
Price:₹22,298 / night
Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK
SUPERHOSTEntire townhouse
Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK
Price:₹19,498 / night
Waterfront Ocean Side House with Dock & Boat Ramp
Entire house
Waterfront Ocean Side House with Dock & Boat Ramp
Price:₹9,974 / night
Key Largo Cozy Cottage! Paradise Awaits You!
SUPERHOSTEntire cottage
Key Largo Cozy Cottage! Paradise Awaits You!
Price:₹14,199 / night
Live-Laugh-Love  In Islamorada
SUPERHOSTPrivate room
Live-Laugh-Love In Islamorada
Price:₹11,999 / night
Conch Life Haven - Private-Parking - Fast Internet
SUPERHOSTEntire guest suite
Conch Life Haven - Private-Parking - Fast Internet
Price:₹11,262 / night
Ocean Breeze & Sunset Skies at Casa Coco
SUPERHOSTCampervan/Motorhome
Ocean Breeze & Sunset Skies at Casa Coco
Price:₹10,424 / night
Summer Time Is Here!. Oceanfront condo /Ocean View
SUPERHOSTEntire apartment
Summer Time Is Here!. Oceanfront condo /Ocean View
Price:₹18,373 / night
Tropical Hideaway Hot Tub in Key Largo/Islamorada
SUPERHOSTEntire cottage
Tropical Hideaway Hot Tub in Key Largo/Islamorada
Price:₹11,374 / night
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