Discover a selection of 1,500 vacation rentals in Islamorada, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $200 per night, and houses and villas are popular options for a stay in Islamorada. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Islamorada
Destination guide

Enjoy island paradise vacation homes on Islamorada

Encompassing 6 of the Florida Keys, Islamorada is a paradise for beachgoers. In addition to its pristine beaches and turquoise waters, Islamorada has an abundance of activities in, under, and above the water for any inclination. Whatever you’re looking for from your beach getaway, vacation home rentals get you right in the center of all Islamorada has to offer.

Things to do

Top island adventures near vacation rentals in Islamorada

Islamorada is a popular destination with a little bit of everything, ranging from watersports and beach activities to historic sites and nature trips. Vacation homes can be found near must-visit places like the Theater of the Sea, a marine park with interactive dolphin and sea lion shows, and Windley Key Fossil Reef Geological Park, a historic limestone quarry with fossilized coral and hiking trails. The History of Diving Museum is great for history and nature lovers, due to its collection of artifacts and exhibits celebrating the evolution of diving. Families will enjoy Founders Park, a 40-acre space with a beach, a pool, sports facilities, a playground, and other recreational spaces. The Rain Barrel Sculpture Gallery, a rustic spot with local sculpture, paintings, pottery, and other works, is a lovely attraction for art lovers.


Beachside nirvana in Islamorada

Islamorada offers an idyllic seaside escape with its many pristine beaches. Vacation rentals are available near some of the best shorelines, such as Anne’s Beach, a pet-friendly, family-friendly area with soft sand, a boardwalk, and seaside essentials, and Holiday Isle Beach, a quiet fishing coastline with colorful marine life, gentle surf, and warm waters. Islamorada Library Beach offers a secluded retreat with stunning views of the water and a nearby park for small children. Long Key State Park, a quiet beach with clear water that’s popular for diving and snorkeling, also has beautiful hiking trails nearby so you can take in the landscape.

How to get there

Transportation to and around Islamorada

The nearest airport is in Marathon, FL (MTH-Florida Keys Marathon), located 30.8 mi (49.5 km) from the city center.

Getting around

Transportation in Islamorada

Islamorada is accessible from mainland Florida by a highway bridge, but once there, you’ll have limitless transportation options to get you to and from the vacation rentals. Shuttle and airport transportation are available, as well as car rentals and taxis, to get you through the area and to nearby destinations. Bikes and motorbikes are available to rent, giving you an opportunity to explore Islamorada on your own schedule, and many destinations are close enough to walk.

Food and drink

Sample Islamorada’s regional cuisine

From authentic Tuscan cuisine to Caribbean favorites, Islamorada offers a range of exciting culinary options to suit every palate. Whether you prefer fresh-caught seafood in a restaurant with ocean views, or you want to settle into a casual restaurant with the kids near your summer rental, the diverse eateries in Islamorada ensure you’ll find just what you need to satisfy your cravings.

How many vacation rentals are available around Islamorada, FL?

Our 2022 property listings offer a large selection of 1,299 vacation rentals around Islamorada. From 751 house rentals to 27 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Islamorada?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Islamorada:

  • Venetian Shores: 71 vacation rentals
  • Lower Matecumbe Beach: 98 vacation rentals
  • White Marlin Beach: 98 vacation rentals
  • Indian Waterways: 45 vacation rentals
  • Toll Gate Shores: 69 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Islamorada?

Vrbo offers a large selection of vacation rentals near lovely places in Islamorada. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Florida Keys Flats Fishing: 1,583 vacation rentals
  • PADDLE! the Florida Keys: 1,582 vacation rentals
  • Florida Keys Dive Center: 1,583 vacation rentals
  • Matecumbe United Methodist Church: 1,385 vacation rentals
  • Founders Park: 1,571 vacation rentals

But there are many other points of interest around Islamorada listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Islamorada?

Yes, of course. Vrbo has 751 Houses in Islamorada. Our other popular types of vacation rentals in Islamorada include:

  • Villas: 27 rentals available
  • Cottages: 11 rentals available
  • Bungalows: 11 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Islamorada?

Yes, you can select your preferred vacation rental with pool among our 942 vacation rentals with pool available in Islamorada. Please use our search bar to access the selection of vacation rentals available.

Explore destinations around Islamorada

Venetian Shores
71 vacation rentals
Lower Matecumbe Beach
98 vacation rentals
White Marlin Beach
98 vacation rentals
Indian Waterways
45 vacation rentals
Toll Gate Shores
69 vacation rentals
Sunshine Estates
73 vacation rentals
Plantation by the Sea
85 vacation rentals
Seabreeze Trailer Park
53 vacation rentals
Coral Cove
21 vacation rentals
Bonefish Bay
36 vacation rentals
Plantation Tropical Park
72 vacation rentals
Plantation Lake Estates
41 vacation rentals