Islamorada vacation rentals

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your current months are May, 2024 and June, 2024.
May 2024
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Select from 631 houses, 112 condos, and other vacation rentals to find the perfect place for your stay in Islamorada. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, including parking and a garden. At the end of the day, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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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.

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.

Exploring the natural landscape of Islamorada

Travelers appreciate the beautiful ocean views and breathtaking sunsets, which is just a taste of what Islamorada has to offer. Whether you're an active traveler or just want to take in the scenery, Islamorada is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Anne's Beach (8.8 mi / 14.1 km)
  • Baker's Cay Resort Beach (13.9 mi / 22.4 km)
  • Long Key State Park (14.4 mi / 23.1 km)
  • John Pennekamp Coral Reef State Park (19.8 mi / 31.8 km)
  • Coco Plum Beach (26.9 mi / 43.4 km)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 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.

Transportation to and around Islamorada

The nearest airport is in Marathon, FL (MTH-Florida Keys Marathon), located 30 mi (48.2 km) from the city center.

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.

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.

Frequently asked questions

What is the best area to stay in Islamorada when booking a vacation rental?

If you're planning a break in Islamorada, Venetian Shores is one of the most sought-after destinations to stay. No matter your style of travel, Vrbo is sure to have a vacation rental here that's just right for you.

What is the most popular type of vacation rental accommodation in Islamorada?

Houses are the most popular style of vacation rental in Islamorada, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect fit.

How much does it cost to rent a vacation rental in Islamorada?

Season, property type and length of stay are some things that can influence the price of a vacation home. Simply add your dates of travel to find your ideal escape. From homey country cottages to expansive villas, all Vrbo vacation rentals offer terrific value.

How much does it cost to rent a beach house in Islamorada?

When you travel and the style and size of the property will influence the cost of your beachside stay. Enter your Islamorada travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you need.

Are there pet-friendly vacation rentals in Islamorada?

Pack a travel bag and a bone for the pup in your life because Islamorada has 166 stays that throw out the welcome mat to doggie guests. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.

Can I rent a house with a pool in Islamorada?

Mark the "pool" box in our filter tool and you can choose from 122 houses with private pools in Islamorada on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your free time is up to you when your vacation property has its own swimming pool.

What are popular rental amenities in Islamorada?

Some of the most popular rental amenities people look for in Islamorada are a barbecue grill, a chef and a sauna. Whether you're on a trip with family, pals or even pets, Vrbo vacation rentals have the best amenities for chilling out with the people you cherish the most.

Are there large group vacation rentals in Islamorada?

You can pick from 18 vacation properties in Islamorada that can host a group of 10 or more guests. Whether you're organizing time away with the family or an event like an anniversary, there's plenty of space to get your loved ones together under the same roof.

Are there vacation rentals in Islamorada that welcome kids?

With 166 family-friendly vacation rentals to select from in Islamorada, now is a great time to introduce the kiddos to the joys of travel. Simply click on our "Properties good for families" filter to locate stays that feature conveniences perfect for traveling families, like dining rooms, pools, entertainment units and bunk beds.

What are the top attractions for families in Islamorada?

There's a ton of amazing things to do and see with the family in Islamorada, such as:

  • Theater of the Sea
  • Annes Beach
  • Robbies

Are there one-bedroom vacation rentals in Islamorada?

Islamorada has 16 one-bedroom rentals on offer. Often positioned in popular areas due to their smaller size, a one-bedroom vacation rental is perfect if you're getting away with your partner or a buddy. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back while discovering this exciting destination.

Can I find two-bedroom vacation rentals in Islamorada?

Take your pick of 57 two-bedroom properties in Islamorada. Settle the kids into the second room or maybe fill it with a couple of your besties. There's space for whoever's lucky enough to be coming along for the ride.

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