Discover a selection of 2,000 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 $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.
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.

Natural features

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)
  • Fiesta Key (11.8 mi / 19 km)
  • Baker's Cay Resort Beach (13.9 mi / 22.4 km)
  • John Pennekamp Coral Reef State Park (23.1 mi / 37.1 km)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 km)
  • Islamorada County Park (4.5 mi / 7.2 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 mi (48.2 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.

What are the top vacation rentals in or near Islamorada?

Whether you're in search of a cozy retreat for you and your sweetheart or someplace spacious to fit all your friends, you'll find some top vacation rentals in and around Islamorada. Here are a couple to get your inspiration flowing:

  • "Sombrero Beach Home On Canal With Private Dock And Heated Pool" is a favorite with guests. Around 35 miles from Islamorada, it has 3 bedrooms and plenty of useful amenities, including towels and WiFi.
  • "Kayak Boot Key Harbor, 75ft Canal Home" is another top pick, offering 2 bedrooms, coffee and tea making facilities, nearby birdwatching activities and more. It's around 35 miles from Islamorada.

For even more great options, use the search bar at the top of the page to find the perfect Islamorada vacation rental for you.

What are the best tiny house vacation rentals in or near Islamorada?

You need only set foot in one of Vrbo's tiny house vacation rentals in Islamorada to figure out that cool things really do come in little packages. Sensibly designed to maximize space, these fun-sized digs deliver a big vacation experience:

  • Take a few days off to recharge your batteries at "Tiny House In Key Largo Paradise". Located in Key Largo, nearby birdwatching activities and a washing machine are just a couple of the amenities you can expect here.
  • "Tiny House Rv, Kayak, Beach, Marina" in Key Largo is another top-rated choice. Pet-friendly services and a garden will make your stay here extra comfortable.

What are the top-rated vacation rentals for weekend getaways in or near Islamorada?

Escape from the rat race at one of our weekend getaways in or near Islamorada. Whether you want to hang out with buddies or spend quality time with the family, we'll have something to suit your style. These top-rated options are hard to beat:

  • Get comfy at "Aquamarine Oceanviewjuly 30". Located around 9 miles to the southwest of Islamorada, this cozy retreat has everything you need for a relaxing stay, including tennis and housekeeping services.
  • "Life In Paradise With Boat Slip At #1 Rated Resort In Marathon" is another popular option. It's located 30 miles to the southwest of Islamorada and features a microwave oven, a balcony and more.

Can I find studio apartments for rent in and around Islamorada?

Studio apartments may be small in size, but they pack a punch when it comes to location and convenience. Unpack your bags and settle into one of these popular studio apartments in and around Islamorada:

  • Enjoy some time out on your own or take a buddy along to "Ocean Front 1/1, Amazing Ocean". You'll have loads of amenities at your fingertips, including a stovetop and tennis.
  • "Spectacular Top Floor Oceanfront View Condo" is another terrific choice, offering all you could want for a heavenly Islamorada vacation. Useful amenities here include a boat and nearby ecotour services.

Can I find short term rentals in or near Islamorada?

Whether you're looking for a compact apartment for you and a pal or a house big enough for the whole family, short-term rentals are easy to find in and around Islamorada. These properties are an ideal base for a quick visit:

  • If you can only spare a few nights, "Ocean View Anglers Reef - Pool" is a good choice. It's close to the center of Islamorada, so you'll be near all the best sights.
  • Alternatively, spend a few relaxing nights at "Aquamarine Oceanviewjuly 30". This centrally located property makes it easy to explore the area's sights.

What are the best romantic weekend getaways in or near Islamorada?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is one of the best ways to add some fire to your relationship. Whisk your honey off for a couple of days at one of these top escapes in or near Islamorada:

  • Sneak away on Friday for a couple of passion-filled evenings at "Coconut Sunsets And Open Water Views". Approximately 30 miles from Islamorada, this place comes with lots of nice touches, including a swimming pool and air conditioning.
  • "Ocean View Anglers Reef - Pool" is another terrific option that's bound to impress. It's approximately 2 miles from Islamorada and comes with beauty services and a dining table.

Are there mansions for rent in or near Islamorada?

Nothing screams "best vacation evvv-er" like staying in a mansion. Treat your loved ones to a truly unforgettable getaway at one of these mansions for rent in or near Islamorada:

  • Located 16 miles to the northeast of Islamorada, "Mediterranean Mansion In Florida Keys" is the perfect place to relax and unwind in luxury. Amenities here include beauty services and a swimming pool.
  • With a fireplace, a swimming pool and loads of other high-end amenities, "Duck Key, Fl Waterfront Mansion For Rent Fl Keys Luxury Home Marathon" will get your squad's nod of approval. This plush retreat is roughly 20 miles to the southwest of Islamorada.

What are the best large group vacation rentals in or near Islamorada?

Vacation with others and boost your odds of having fun. Whether you're planning an active escape with pals or a family reunion, there's no shortage of large group vacation rentals in and around Islamorada:

  • A nice range of amenities including a kitchen and a nearby waterfront make "Paradise Home Away From Home" a top pick. This sizable getaway has 4 bedrooms and sleeps up to 12 guests. From the center of Islamorada, it's around 17 miles away to the northeast.
  • "Beautiful Oceanfront Oasis With Pool" is another excellent option. It's around 0.1 miles to the southwest of Islamorada, has 4 bedrooms and accommodates up to 12 guests. A nearby waterfront and a swimming pool are just a couple of things designed to make your group vacation more comfortable.

What are the best houses for rent with a pool in or near Islamorada?

Nothing screams fun like a pool. Pull out your inflatable flamingo and check out these houses in or near Islamorada that feature this vacation perk:

  • Get comfortable at "Spacious Ground Level Gulf Side House W", where your main priority will be pool time. Amenities such as a porch and coffee and tea making facilities help make this escape a favorite with guests.
  • Otherwise, unpack your suitcase at "Best Kept Secret House Boat 70' Has Everything". As well as its inviting pool, you'll also have use of a separate dining area and a living room.

Unsure how to pack for your Islamorada escape? This appealing destination has a tropical savanna climate. During the summer months, you can expect average temperatures ranging from 80 ºF to 85 ºF. Scroll through our range of Islamorada vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Islamorada?

It's always more fun when you share those special memories with the folks you love the most. Whether you're organizing a family get-together or spending time with good friends, Vrbo has a large vacation rental that's right for you. These are two of our best in and around Islamorada:

  • Located around 30 miles to the southwest of Islamorada, "Life In Paradise With Boat Slip At #1 Rated Resort In Marathon" has 3 bedrooms and sleeps up to 8 guests. It comes with a range of amenities, including coffee and tea making facilities and a kitchen.
  • "Spacious Ground Level Gulf Side House W" also has the space you need to live it up with loved ones. This property is around 30 miles to the southwest of Islamorada, and accommodates as many as 8 guests in its 3 bedrooms. A toaster and a kitchen will help keep everyone comfortable and happy.

If you'd like to sightsee, there are lots of family-friendly attractions nearby to put on your itinerary. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge are excellent places to start.

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