Islamorada House Rentals

Compare 10 vacation rentals.
USA > Florida > Islamorada

Make Islamorada your next getaway

Quaint island living, plenty of fun in the sun activities, and access to world-class sport fishing are ready to greet you when you stay at one of our Islamorada house rentals. Islamorada is a popular destination for those seeking year-round warm weather, beautiful white sand beaches, and a laid-back island vibe. 

Explore Islamorada house rentals, condo rentals, and more


House rentals

View 8 House rentals

Condo rentals

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Islamorada vacation rentals for every getaway

Dog-friendly Hot tub Internet
Tollgate Tides
2 Bedroom | 2 Bath | Sleeps 6

Tollgate Tides - Islamorada, FL

$157 avg / night
Escape to the Keys A6
2 Bedroom | 2.5 Bath | Sleeps 8

Escape to the Keys A6 - Islamorada, FL

$131 avg / night
Waterfront Wonder
6 Bedroom | 5.5 Bath | Sleeps 10

Waterfront Wonder - Islamorada, FL

$1,000 avg / night
Two White Turtles
2 Bedroom | 2 Bath | Sleeps 4

Two White Turtles - Islamorada, FL

$124 avg / night
Executive Bay Club Condo M-1
2 Bedroom | 2 Bath | Sleeps 6

Executive Bay Club Condo M-1 - Islamorada, FL

$130 avg / night

View 5 more homes

Recent Islamorada vacation rental reviews

From the moment you pull up to the house you are greeted by tropical beauty! Not only is the house on the outside gorgeous and impressive but the inside is a pure luxury getaway. The rooms are decorated lovely and the beds are so comfortable! The views from three of the bedrooms are absolutely stunning. Out the windows you see a clean beach with palm trees and the inviting ocean. Didn’t take me long to grab a beach chair and head down to sit by the water. It was also nice to sit on the canal side under the tiki hut and watch the boats go by. What an amazing place to vacation!
Dawn P. | Sep 2023
Good: Great location, Well appointed, recent renovation. Bad: Ice maker didn't work. BBQ tank ran empty, narrow dead end st.
Jeff M. | Jun 2023
The place was very clean and was able to accommodate our party comfortably with a lot of beds. The unit was located in a beautiful community with a stunning beach, pickleball courts, tennis courts, and a dock. The staff was so helpful with any questions we had, and it was truly one of the best experiences ever. If you are on the fence, I would definitely recommend it.
Jonathan B. | Jun 2023
Islamorada vacation rental FAQ

Yes, 7 of our Islamorada homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 33 of our Islamorada vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Islamorada vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Islamorada team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Islamorada, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Things to do around your Islamorada vacation rental

Located between the Florida Key islands of Key Largo to the east and Marathon Key to the west, Islamorada offers a wide range of activities from snorkeling to paragliding to landing trophy tarpon and marlin in the area’s warm coastal waters, making it well-suited for adventurers and families.

Kids will love interacting with the area’s abundant sea life at the Theater of the Sea marine mammal park, where they can toss mackerel to hungry sea lions, swim with dolphins, and get up close to endangered sea turtles. They might also enjoy learning about the island’s mangrove swamps and exotic coastal habitat aboard a Family Fun Boat Tour, where they’ll surely have close encounters with egrets, herons, gulls, and other avian residents of the island.

For more adult tastes, Islamorada offers a plethora of lively options, ranging from great dining at any of the area’s fresh-from-the-boat seafood restaurants to live reggae, bluegrass, and other music festivals throughout the year at ICE Amphitheater at Founder’s Park on Plantation Key. Whatever your vacation plans may entail, a stay in one of our Islamorada house or condo rentals provides an excellent home base.

Outdoor adventures near your Islamorada house rental

For those who like to get out and explore nature, Islamorada offers unmatched access to a wide range of activities on both land and water. Take a self-guided walk through lush nature trails on 965 acres of pristine old growth mangrove, mahogany, and poisonwood marshland at Long Key State Park, or unearth buried treasure and artifacts from a Spanish ship that sunk in 1733 at Indian Key Historic State Park. If you prefer to stay dry, rent kayaks or a boat to tour the ancient coral reef and the tropical forest that thrives above at the Lignumvitae Key Botanical State Park on tiny Lignumvitae Key.

Day trips from your Islamorada vacation home

On the north end of the key islands, Islamorada offers quick access to the mainland, which is only 40 miles to the north. Drive north another 40 miles to arrive in Miami, a city known for its thriving nightlife, great shopping, and Latin-focused dining. Thousands of acres of swampland that are home to alligators, cranes, snakes, and many other native species await only 53 miles away at Everglades National Park. Marathon, Big Pine, Sugarloaf, and Key West islands all lie within 80 miles of your Islamorada house rental.

For a fantastic home base in the Florida Keys, a stay in any of our Islamorada vacation homes or condos is one you won’t soon forget!

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