Skip to content
Sign up
Log in
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.

The Island Dog Conch House 2 Bedoom Islamorada FL
SUPERHOSTEntire villa · 5 guests · 3 beds · 1 bath
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.”

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.”

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!”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Islamorada vacation rentals

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

Other great vacation rentals in Islamorada

Live-Laugh-Love  In Islamorada
SUPERHOSTPrivate room
Live-Laugh-Love In Islamorada
Price:€142 / night
Capt Craigs Guest Quarters
Remodeled 1/1 Apartment
SUPERHOSTEntire apartment
Capt Craigs Guest Quarters Remodeled 1/1 Apartment
Price:€123 / night
Garden apartment in unique setting
Entire apartment
Garden apartment in unique setting
Price:€128 / night
Sunset Villas, 1-bedroom suite w/ Full Kitchen
SUPERHOSTEntire apartment
Sunset Villas, 1-bedroom suite w/ Full Kitchen
Price:€117 / night
Paradise in The Anchorage Resort Key Largo
Entire apartment
Paradise in The Anchorage Resort Key Largo
Price:€81 / night
A Piece Of Paradise, New Lic. Key Largo House 3/2
SUPERHOSTEntire house
A Piece Of Paradise, New Lic. Key Largo House 3/2
Price:€51 / night
Conch Life Haven - Private-Parking - Fast Internet
SUPERHOSTEntire guest suite
Conch Life Haven - Private-Parking - Fast Internet
Price:€129 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
NEW Secret Keys Waterfront Hideout has EVERYTHING!
Price:€234 / night
Spring and Summer at Paradise
SUPERHOSTEntire villa
Spring and Summer at Paradise
Price:€340 / night
Canal Waterfront on Duck Key Private Dock & Pool.
SUPERHOSTEntire house
Canal Waterfront on Duck Key Private Dock & Pool.
Price:€277 / night
Keys living with Breathtaking Oceanfront view
Entire house
Keys living with Breathtaking Oceanfront view
Price:€132 / night
Keys Great Weekend Get Away
Private room
Keys Great Weekend Get Away
Price:€77 / night
Show all