Islamorada House Rentals

Compare 5 vacation rentals. Enter your trip dates to get started.
USA > Florida > Islamorada

Make Islamorada your next getaway—choose from 5 great vacation rentals

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 4 House rentals

Condo rentals

View 1 Condo rentals

Islamorada vacation rentals for every getaway

Dog-friendly Hot tub Internet
Sun-kissed Bliss 3D Tour
3 Bed | 3 Bath | Sleeps 6

Sun-kissed Bliss - Islamorada, FL

From $221
Islamorada Oasis
2 Bed | 2.5 Bath | Sleeps 7

Islamorada Oasis - Islamorada, FL

From $315
Paradise Beach 3D Tour
3 Bed | 3 Bath | Sleeps 8

Paradise Beach - Islamorada, FL

From $285
Executive Bay Club Condo M-1 3D Tour
2 Bed | 2 Bath | Sleeps 6

Executive Bay Club Condo M-1 - Islamorada, FL

From $113
Ocean Oasis 3D Tour
5 Bed | 4 Bath | Sleeps 14

Ocean Oasis - Islamorada, FL

From $1,071

View 0 more homes

Recent Islamorada vacation rental reviews

This home is located with a direct view of the ocean but also has canal access for boats. The quiet lane leading to the home provides a a very beachy feel to the area. A great place to relax and enjoy the ocean. This review was submitted while the home was managed by a different property management company.
. | May 2021
This condo was amazing to stay in. My husband with our 3 children had to get away and with virtual schooling we decided to escape to the Keys for a month. This was the first vacation where all of us were in tears to leave and wish we would have booked a longer stay. From the second we walked in the door we were thoroughly impressed with how immaculate and well appointed the condo was. The condo was abundantly stocked with towels and sheets for our stay. All the appliances were immaculately cleaned and most import the WiFi signal was strong!! Plenty of fishing off the private dock in the complex and the beach are was great too. The majority of the residents of the complex were very nice, however when the snowbirds came in after Christmas, they tended to get a little territorial at the pool! About 3 days before our stay was over, we no longer were getting hot water. We called Vacassa and they helped guide us through the process to reset the water heater. When that did not work, a plumber was at our house about 2 hours later, so we were very thankful for their prompt response. My only feedback would be that for the rental price paid, basic cable should be included at least in the living room. Only Netflix, Hulu, and Samsung smart TV channels (think Baywatch and Kitchen Nightmares on 24/7) were available on the TV’s. I hope we can come back soon!
Christopher M. | Jan 2021

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!

Discover Islamorada

4 Florida Keys Races and Marathons for Every Skill Level

Plan your Florida Keys snorkeling vacation