Islamorada, Florida Vacation Rentals

Explore 896 rental homes and villas in Islamorada, Florida for your next vacation or business travel. With private vacation home rentals, enjoy a more personalized stay and a wide range of amenities such as Homes with Pools, Air Condition Homes and Pet-Friendly Homes. With a wide range of homes to offer, pricing can start as low as $60 per night with homes containing as many as 8 bedrooms and 8 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

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Islamorada Overview
Nestled in the aquamarine embrace of the Florida Keys, Islamorada, the "Village of Islands," beckons travelers with its enchanting blend of natural beauty and leisurely charm. This tropical haven, strung across six islands, offers an idyllic retreat for those seeking both adventure and tranquility. Islamorada is renowned as the Sportfishing Capital of the World, a title it wears proudly. Anglers from across the globe flock here to chase the thrill of hooking sailfish, tarpon, and bonefish in the abundant waters. The fishing opportunities are as diverse as the marine life, with deep-sea charters, backcountry fly fishing, and pier fishing all within easy reach. The allure of Islamorada extends beneath the waves, where snorkelers and scuba divers are mesmerized by the underwater tapestry of the Florida Keys National Marine Sanctuary. This protected area is a kaleidoscope of marine life and coral formations, offering an underwater adventure that rivals any across the globe. For those who prefer the serenity of the surface, the calm, clear waters invite kayaking and paddleboarding through lush mangrove trails. Boating and sailing enthusiasts will find bliss here, with a myriad of rental options to navigate the serene waters at their own pace. Islamorada's dedication to marine conservation shines through at Theater of the Sea, where interactive encounters with dolphins and sea lions delight visitors of all ages. The History of Diving Museum offers a fascinating glimpse into the depths of diving history, celebrating the region's submerged wonders. The islands' artistic spirit thrives in local galleries and studios, where the vibrant arts scene is fueled by the Keys' breathtaking vistas. The Morada Way Arts & Cultural District's monthly art walk is a celebration of creativity, featuring live music, exquisite art, and the flavors of local cuisine. Speaking of flavors, Islamorada's dining landscape is a tapestry of fresh catches and tropical zest. Waterfront dining is a feast for the senses, offering stunning views and the freshest seafood, from the delicate sweetness of stone crab to the tangy zest of key lime pie. To elevate your stay, consider the luxury of renting a private home, a sanctuary where you can bask in the comfort of your own space. Many of these homes come with the added indulgence of a swimming pool, perfect for a refreshing dip under the Florida sun. With a variety of pet-friendly options, your furry companions can join in the island reverie. The experience of Islamorada is made even more magical by its beaches and waterfronts. Imagine unwinding on your private slice of paradise or sipping a cocktail as the sun melts into the ocean, painting the sky with fiery hues. This is the quintessence of the Florida Keys lifestyle—a blend of relaxation, recreation, and awe-inspiring natural beauty that makes Islamorada an unforgettable escape.
Cultural Attractions in Islamorada
Islamorada, nestled in the heart of the Florida Keys, offers a unique blend of cultural activities set against a backdrop of stunning natural beauty. While it may be renowned for its fishing and water sports, the "Village of Islands" also caters to those with a passion for the arts, history, and local customs. Begin your cultural journey at the History of Diving Museum, where you can delve into the heritage of underwater exploration. The museum's extensive collection of diving apparatus and artifacts tells the story of mankind's quest to explore the depths of the sea. Interactive exhibits and monthly seminars enrich the experience, making it a must-visit for history enthusiasts. Art lovers will find solace in the local art scene, with galleries like the Gallery Morada and the Redbone Gallery showcasing the works of local and national artists. These galleries feature a variety of mediums, from sculpture and pottery to paintings and photography, all inspired by the vibrant colors and relaxed lifestyle of the Keys. For a taste of local customs and live music, the Morada Way Arts & Cultural District hosts the Third Thursday Art Walk, an event where visitors can enjoy live music, fine art, and a glimpse into the creative spirit of the islands. Stroll down the Morada Way and engage with artists, musicians, and fellow art aficionaries in a festive atmosphere. Theatre buffs will be delighted by the performances at the Keys History & Discovery Center, which often hosts plays and presentations that bring the rich history of the Florida Keys to life. The center itself is a treasure trove of local history, with exhibits that explore the ecology, economy, and cultural heritage of the islands. Islamorada's cultural offerings extend to its culinary scene, where the local cuisine is a reflection of the island's history and traditions. Seafood is a staple here, and many restaurants offer live music to accompany your dining experience, providing a harmonious blend of taste and sound. Festivals and events throughout the year celebrate the island's culture and heritage. The annual Island Fest features live music, art, and food, while the Baygrass Bluegrass Festival showcases some of the best bluegrass music in the South. In Islamorada, the arts and history are as much a part of the landscape as the sun and sea. It's a place where culture thrives amidst the natural splendor of the Florida Keys, offering a serene yet stimulating getaway for those who seek a cultural retreat.
Kids IconFamily friendly activities in Islamorada
Islamorada, nestled in the heart of the Florida Keys, is a paradise for families traveling with children, offering a blend of adventure, relaxation, and educational experiences that cater to the curiosity and energy of young minds. Begin your family adventure at the Theater of the Sea, an intimate marine mammal park where children can get up close with dolphins, sea lions, and rays. The park offers interactive programs like swimming with dolphins and sea lions, which are both educational and thrilling for kids. The lagoon-side beach and the bottomless boat ride add to the charm, making it a full day of fun. For those little adventurers, Robbie's Marina of Islamorada is a must-visit. Here, families can feed the massive tarpon from the docks, an experience that is sure to elicit gasps and giggles. The marina also offers kayak and boat rentals for exploring the mangrove-fringed waters, and the on-site restaurant provides a casual setting to enjoy the local catch. The Florida Keys History & Discovery Center is a treasure trove for curious minds. With exhibits on the history, ecology, and people of the Keys, it's a great place for kids to learn about the region's unique environment and cultural heritage. The center's aquarium and interactive displays make the learning experience engaging for children. Islamorada also boasts beautiful beaches like Anne's Beach, where shallow waters provide a safe environment for kids to splash around and the boardwalk offers a scenic stroll. The beach's natural beauty is a perfect backdrop for a family picnic or a day spent building sandcastles. For a unique experience, take a family eco-tour or snorkeling trip to explore the vibrant coral reefs that lie just offshore. Companies like A Family Fun Boat Tour Co. cater to families, ensuring that even the youngest members can safely enjoy the wonders of the underwater world. Fishing enthusiasts, both young and old, will find Islamorada to be an angler's dream. Known as the Sportfishing Capital of the World, the area offers numerous charters that are happy to tailor trips to families, making it an exciting way to introduce children to the sport. In Islamorada, the blend of educational attractions, natural beauty, and family-oriented activities create an environment where children can learn, play, and make memories that will last a lifetime. Whether your family is seeking adventure on the water or a peaceful day surrounded by nature, Islamorada is a destination that will delight travelers of all ages.
Nature IconOutdoor activities in Islamorada
Islamorada, nestled in the heart of the Florida Keys, is a paradise for outdoor enthusiasts and nature lovers. Known as the "Village of Islands," it spans approximately 20 miles and is a collection of tropical islands including Plantation Key, Windley Key, Upper and Lower Matecumbe Keys, and the offshore islands of Indian Key and Lignumvitae Key. For those who seek to immerse themselves in the natural world, Islamorada offers an abundance of activities. The clear, warm waters surrounding the islands are a haven for snorkelers and scuba divers, with the Florida Keys National Marine Sanctuary providing a protected environment for a diverse array of marine life. The coral reefs, such as Cheeca Rocks and Alligator Reef, teem with colorful fish, sea turtles, and other aquatic creatures. Anglers will find Islamorada to be a dream destination, often referred to as the Sportfishing Capital of the World. The backcountry waters are home to tarpon, bonefish, and permit, while offshore fishing can yield sailfish, mahi-mahi, and tuna. Numerous charter services are available to guide both novice and experienced fishermen to the best spots. For a more leisurely pace, kayaking and paddleboarding through the mangrove-lined channels offer a serene way to explore the local ecosystem. Paddlers can glide over seagrass beds, spot a variety of birds, and even encounter manatees in the shallow waters. Nature lovers will appreciate the beauty of Lignumvitae Key Botanical State Park, accessible only by boat. This island is a tropical hardwood hammock that hosts a variety of rare plants and birds. Guided tours provide insight into the island's unique ecology and history. Theater of the Sea, an intimate marine mammal park, allows visitors to interact with dolphins, sea lions, and rays in a series of encounters and shows. It's an educational and entertaining experience that highlights the importance of conservation. For a glimpse into the history and culture of the area, Indian Key Historic State Park is an offshore island that can be reached by kayak or boat. It was once the site of a shipwreck salvage community in the early 19th century and now offers trails and interpretive signage amidst the ruins. With its stunning natural beauty, abundant wildlife, and myriad of water-based activities, Islamorada is a destination that truly embodies the spirit of the great outdoors. Whether you're seeking adventure on the high seas or tranquility among the mangroves, this tropical locale offers an unforgettable experience for nature enthusiasts.
Weather IconWeather in Islamorada
Islamorada, nestled in the heart of the Florida Keys, is a tropical paradise that enjoys a warm and inviting climate year-round, making it a favorite for sun-seekers and outdoor enthusiasts alike. The weather in Islamorada is characterized by its subtropical climate, which means you can expect warm temperatures, plenty of sunshine, and a fair amount of humidity. During the winter months, from December to February, the weather is typically the most pleasant, with average high temperatures ranging from the mid-70s to low 80s Fahrenheit (around 24-28°C). This is the dry season, so rainfall is minimal, and the humidity is lower, making it an ideal time for fishing, boating, and exploring the natural beauty of the Keys. Spring, from March to May, sees a gradual increase in both temperature and humidity. The highs average in the low to mid-80s Fahrenheit (around 27-30°C), and the chance of rain begins to increase as the season progresses. This is a wonderful time to visit for those looking to enjoy the outdoors before the summer heat sets in. Summer, from June to August, is the hottest and most humid time of the year, with temperatures often reaching into the 90s Fahrenheit (around 32-37°C). This is also the rainy season, with short, heavy showers and thunderstorms being common in the afternoons. Despite the heat, the warm ocean waters and the vibrant marine life make this a popular time for snorkeling, diving, and enjoying the island's water sports. Autumn, from September to November, brings a slight relief from the summer heat, with temperatures gradually cooling to the mid-80s Fahrenheit (around 29-30°C). However, this is also the peak of hurricane season, and while direct hits are rare, it's important to be aware of the weather forecasts and have flexible travel plans during this time. The most popular weather conditions in Islamorada are prevalent during the winter and early spring months when the temperatures are warm but not too hot, and the chance of rain is lower. This is when the climate is especially pleasant, offering the perfect backdrop for the island's many festivals, outdoor activities, and stunning sunsets. No matter when you choose to visit, Islamorada's laid-back atmosphere and beautiful weather make it a year-round destination for those looking to escape to a tropical oasis.
Transportation in Islamorada
Islamorada, known as the "Village of Islands," is a key destination within the Florida Keys, offering a tropical escape with a laid-back atmosphere. This village is a string of islands including Plantation Key, Windley Key, Upper and Lower Matecumbe Keys, and the offshore islands of Indian Key and Lignumvitae Key. Most visitors arrive in Islamorada by car, driving along the scenic Overseas Highway (U.S. Highway 1), which connects the chain of islands in the Florida Keys. This drive offers breathtaking ocean views and is an experience in itself. For those flying in, the nearest major airport is Miami International Airport, approximately 80 miles away. From Miami, travelers can rent a car or take a shuttle service to reach Islamorada. Once in Islamorada, transportation options are more limited compared to larger cities. There is no formal public transportation system on the islands, so having a car is the most convenient way to explore the area. Car rentals are available from the airport or from rental agencies in the Keys. For those who prefer not to drive, taxi services and ride-sharing options like Uber and Lyft are available, though they may be less frequent than in urban areas. Islamorada is also a popular destination for boating. Many visitors choose to explore the surrounding waters by renting a boat or joining a guided tour, which can include fishing, snorkeling, or simply cruising the beautiful Florida Bay and Atlantic Ocean. While Islamorada is not known for being particularly walkable due to the spread-out nature of its attractions and amenities, some areas, such as the Morada Way Arts & Cultural District, offer a pleasant pedestrian experience with galleries, shops, and restaurants within walking distance of each other. Biking is another enjoyable way to get around, with some resorts and businesses offering bike rentals to guests. For those looking to explore the natural beauty of the Keys, guided eco-tours and water sports equipment rentals are widely available, providing opportunities to experience the local marine life and coral reefs. In summary, while Islamorada may not have the extensive transportation infrastructure of a major city, it offers a variety of options suitable for island exploration. Renting a car provides the most flexibility, but for those looking to enjoy the water or stay local, boats, bikes, and walking can also be part of the quintessential Florida Keys experience.