Discover a selection of 1,000 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 $143 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.
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.


Activities and attractions in and around Islamorada

Do you want to find things to do during your stay? Travelers enjoy fun activities like fishing and diving. Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Islamorada a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Dolphin Research Center (23.6 mi / 38 km)
  • Bud n' Mary's Dive Center (3.5 mi / 5.7 km)
  • Florida Keys Wild Bird Rehabilitation Center (9.9 mi / 15.9 km)
  • Dolphins Plus (15.1 mi / 24.3 km)
  • Dolphins Plus Bayside (17.9 mi / 28.8 km)
  • MarineLab Undersea Laboratory (19.5 mi / 31.3 km)

Seasonal weather averages in Islamorada

Travelers enjoy Islamorada for its diving. If you're hoping to enjoy some warm-weather activities on your vacation, August, July, June and September are the hottest months to visit, when temperatures average 91°F.

Natural features

Exploring the natural features in Islamorada

Travelers love Islamorada for its beautiful ocean views and breathtaking sunsets. Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Islamorada is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Windley Key Fossil Reef Geological State Park (1.7 mi / 2.8 km)
  • Founders Park (3.6 mi / 5.8 km)
  • Plantation Key (4.7 mi / 7.6 km)
  • Lignumvitae Key Botanical State Park (5.3 mi / 8.6 km)
  • Anne's Beach (9.7 mi / 15.6 km)
  • Harry Harris Park (9.9 mi / 15.9 km)

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 (49.6 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.

Essential info

Key information for staying in Islamorada vacation rentals

Islamorada is a laid-back beach area with a population of 6,600 and a tropical climate, offering sunshine and warm temperatures. As a popular tourist destination, Islamorada is a generally safe and friendly area, though it’s best to exercise caution with valuables in your car or vacation home while on your trip. Police services are provided by the Sheriff of Monroe County, and hospital and medical services are available. In the event of an emergency, dial 9-1-1.

How many vacation rentals are available around Islamorada, FL?

Our 2020 property listings offer a large selection of 1,185 vacation rentals around Islamorada. From 663 house rentals to 28 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:

  • White Marlin Beach: 90 vacation rentals
  • Venetian Shores: 69 vacation rentals
  • Sunshine Estates: 68 vacation rentals
  • Bonefish Bay: 33 vacation rentals
  • Toll Gate Shores: 66 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:

  • Theater of the Sea: 1,352 vacation rentals
  • Founders Park: 1,393 vacation rentals
  • Windley Key Fossil Reef Geological State Park: 1,352 vacation rentals
  • Bud n' Mary's Dive Center: 1,243 vacation rentals
  • Hurricane Monument: 1,239 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 663 Houses in Islamorada. Our other popular types of vacation rentals in Islamorada include:

  • Villas: 28 rentals available
  • Cottages: 14 rentals available
  • Bungalows: 14 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 905 vacation rentals with pool available in Islamorada. Please use our search bar to access the selection of vacation rentals available.

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