Islamorada Vacation Rentals: house rentals & more

Discover a selection of 1,000 vacation rentals in Islamorada 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 $185 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.

DynamicDestinationRefinements

AsyncDestinationUrgency

Find the best place to stay — Islamorada

Search 1,182 vacation rentals

Stayed May 2021

Family wedding trip!

Property was excellent and just as advertised. We went to Islamorada for a wedding and the house was just perfect. Host was extremely accommodating and the checkin and our process was excellent. I would strongly recommend this property and host. Grea...

Stayed May 2021

Wonderful

PARADISE is all I can say. What a wonderful place. Relaxing for a quiet getaway but close enough to any activity you desire. We had the pleasure of meeting the owners and they were fabulous. They responded very quickly to all our inquiries prior to o...

Stayed May 2021

Perfect location for a relaxing Florida Keys stay!

Jo was amazing from the start! We had an issue with our travel plans and Jo was so amenable to a last minute switch of dates as well as letting us tack two additional days onto our trip. She answered all questions quickly and we felt well taken care ...

Stayed May 2021

Perfect!!

Carmen and Pablo were really great hosts!! Even when she was not feeling well she responded to any questions that we had and we hope that you are feeling better!! The property is just as described and everything on the description and in the pics are...

Stayed Apr 2021

Wow, just Wow!

Need I say more! We were a group of two couples celebrating wedding anniversaries. All we wanted to do was relax by the ocean and play cornhole. Gabriel was kind enough to provide a corn hole game at our request, something we would have gladly bought...

Stayed Apr 2021

Tranquility

Can’t say anything bad about our stay at The Island Dog. House was perfect for us. Awesome private quite older community! Close to robbies and all other restaurants! Cute little but just the right size pool, launching ramp for boat, kayak, or in our ...

Stayed Apr 2021

Perfect Family Get away

We recently stayed one week at Anglers Reef. It was a perfect place for our family and two little girls. The home was comfortable, clean and communication with the property manager was really easy. Having the swimming pool and private beaches availab...

Stayed Apr 2021

The Lucky Lobster is wonderful.

We loved our stay at the Lucky Lobster. The house was sparkling clean and had everything we needed. The beds are super comfy, the kitchen was well stocked, the beach towels were perfect, and the location is amazing. Anglers Reef is a peaceful communi...

AsyncDestinationInfographic

AsyncExploreBookEnjoy

Destination guide

Find a beach rental in Islamorada

The village of Islamorada is a top destination for a Florida Keys beach rental. Encompassing 6 of the keys, Islamorada is a popular place for sport fishing, scuba diving, and snorkeling the coral reefs. You’ll find endless stretches of beach for sunbathing and swimming on the tropical coasts of the village. For land adventures, you could visit the Windley Key Fossil Reef Geological Park, Lignumvitae Key Botanical State Park, and Indian Key Historic State Park, which boasts fascinating ruin sites. You’ll also like the History of Diving Museum exhibits from shipwrecks and the Theater of the Sea, which has dolphin encounters.

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

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)

Weather

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)

Beaches

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?

Our 2021 property listings offer a large selection of 1,182 vacation rentals around Islamorada. From 670 house rentals to 33 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.