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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.

Sailboat - Swim/Snorkel/Kayak
Boat · 2 guests · 1 bed · 1 bath
Sailboat - Swim/Snorkel/Kayak

Our rustic, yet clean and comfortable 24' Columbia sleep aboard offers the experience of sleeping on a boat but provides land amenities such as a restroom facility (toilet and shower), fridge and microwave, barbecue grills , picnic tables, etc.

The Sand Castle - A Private Suite in Paradise
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
The Sand Castle - A Private Suite in Paradise

Stay at “The Sand Castle” directly on the Bay! The sunsets are stunning! Feed the fish! See the dolphins swimming in the bay. Learn all about the Keys from Captain Randy. Your room is a waterfront private tropical suite with a King size bed and private bath. This is completely separate from our main house. Boat rides and fishing trip available. Minutes from beaches & boat ramps. Come stay with us and share a little “peace” of paradise. Kayaks available to rent.

What guests are saying:

“Randy and Tamera's place is an absolute jewel on Tavenier. This home is nestled into a beautiful dead end stree within a small community of waterfront homes. Randy keeps his boat here for tours, rental kayaks for a short paddle to the mangrove island just a few rows from his home, and with that the most incredible dock. He has two benches to sit and watch the thousands of fish and critters that wander by and if you like that you'll love to see the water lit up at night witb pool lights along the dock. We saw snapper, needle fish, a lobster, manatee, baracuda, tarpon, and even nurse sharks. We only spent a night here andso you can imagine the dock is active. The room is beautiful with an awesome shower and king size bed, tv, fridge, keurig, and anything else you may need. There is plenty of parking and the tennant quarters are completely separate for your privacy. This location is such a bargain, you have to stop by.”

WATER VIEWS ON  J. PENNEKAMP Free Kayaks
SUPERHOSTEntire house · 5 guests · 3 beds · 1 bath
WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, 2 Large Balconies Totally renovated all the amenities of home. Free use of kayaks at the house. Kayak John pennekamp state park steps away from front door. 29 foot boat available 4 all water activities I captain the boat.

What guests are saying:

“Beautiful tranquil home with wonderful water views from the upper balcony and the front porch. This was a quiet sanctuary for our family the past week in the recent series of events. Easy drive or kayak across to Pennekamp state park and paddle the mangroves. Also great snorkeling and highly recommend the Eco boat tour- saw manatees and learned so much about the ecology of the Keys. Only about an 1.5 hr drive from the Everglades National Park which also recommend visiting. You won’t be disappointed if you choose this rental! The owners were gracious and allowed us to stay later on our last day to avoid the airport which we were grateful for. Thank-you!”

Vacation rentals for every style

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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

Conch Life Haven - Private-Parking - Fast Internet
SUPERHOSTEntire guest suite
Conch Life Haven - Private-Parking - Fast Internet
Price:ﺩ.ﺇ 544 / night
NEW Secret Keys Waterfront Hideout has EVERYTHING!
SUPERHOSTEntire guest suite
NEW Secret Keys Waterfront Hideout has EVERYTHING!
Price:ﺩ.ﺇ 899 / night
360 DEGREE WATERVIEW HOUSEBOAT
SUPERHOSTBoat
360 DEGREE WATERVIEW HOUSEBOAT
Price:ﺩ.ﺇ 661 / night
Island Sanctuary Islamorada
SUPERHOSTBoat
Island Sanctuary Islamorada
Price:ﺩ.ﺇ 918 / night
Cottage - Waterview, Kayak, Snorkel
Entire guest suite
Cottage - Waterview, Kayak, Snorkel
Price:ﺩ.ﺇ 606 / night
Efficiency - Snorkel, Swim, Kayak
Entire guest suite
Efficiency - Snorkel, Swim, Kayak
Price:ﺩ.ﺇ 507 / night
Casa Fish LLC
SUPERHOSTEntire townhouse
Casa Fish LLC
Price:ﺩ.ﺇ 716 / night
Your Keys Getaway!
SUPERHOSTEntire house
Your Keys Getaway!
Price:ﺩ.ﺇ 459 / night
Island Get Away
SUPERHOSTEntire guest suite
Island Get Away
Price:ﺩ.ﺇ 511 / night
House - Waterview, Kayak, Snorkel
Entire bungalow
House - Waterview, Kayak, Snorkel
Price:ﺩ.ﺇ 716 / night
Wht.Beach 5 min. Paddle.Hom.1-6ppl/1-30nite (W)
Private room
Wht.Beach 5 min. Paddle.Hom.1-6ppl/1-30nite (W)
Price:ﺩ.ﺇ 483 / night
FLAKEYS BED & BEER ****EXTRA CLEAN*****
SUPERHOSTEntire house
FLAKEYS BED & BEER ****EXTRA CLEAN*****
Price:ﺩ.ﺇ 588 / night
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