Longboat Key, Florida Vacation Rentals

Explore 703 rental homes and villas in Longboat Key, 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 Best Affordable Homes. With a wide range of homes to offer, pricing can start as low as $59 per night with homes containing as many as 10 bedrooms and 11 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

Types of vacation rentals in Longboat Key

Where to stay in Longboat Key

Show all homes

Booking a vacation rental in Longboat Key, Florida?

Here are some things to know to support your visit:

Longboat Key Overview
Nestled between the shimmering Gulf of Mexico and the serene Sarasota Bay, Longboat Key is a slice of paradise that beckons with its pristine beaches and an atmosphere of exclusive tranquility. This barrier island, with its 12-mile stretch of powdery white sands, is a sanctuary for those seeking to immerse themselves in the soothing rhythms of coastal life. Here, the days end with spectacular sunsets that cascade the sky in a symphony of colors, a daily spectacle that is best enjoyed from the privacy of a beachfront home. Imagine waking up to the gentle sound of waves in a luxurious private home, where the day's agenda is yours to craft. Longboat Key offers an array of exquisite home rentals, many with their own swimming pools, where you can bask in the Florida sun in complete seclusion. These homes, often pet-friendly, ensure that your entire family, including your four-legged members, can relax in comfort and style. The privacy of a home rental elevates your experience, providing a personal oasis away from the crowds. The island's allure extends beyond its beaches. The crystalline waters surrounding Longboat Key are a playground for water sports enthusiasts. Rent a kayak, paddleboard, or jet ski to glide over the calm sea, or join a guided boat tour to witness the playful dance of dolphins and manatees. Anglers will delight in the bountiful fishing opportunities that await both inshore and offshore. Golfers will find their bliss on Longboat Key's immaculate courses, where the challenge of the game is matched only by the beauty of the lush surroundings. Tennis aficionados, too, will discover exceptional facilities that cater to every skill level, all set against the backdrop of the island's natural splendor. For those who revel in the outdoors, the island's dedication to conservation is evident in its nature preserves. Meander through the trails of Quick Point Nature Preserve or Joan M. Durante Community Park, where the local flora and fauna offer a tranquil retreat for birdwatchers and nature enthusiasts alike. Culinary experiences on Longboat Key are as refreshing as the Gulf breeze, with a focus on fresh seafood and waterfront dining. The island's restaurants range from laid-back beachside grills to sophisticated establishments, all emphasizing the region's freshest offerings and the catch of the day. When the urge for shopping strikes, the island's boutiques and galleries present a curated selection of art, jewelry, and fashion. A short drive away, the chic St. Armands Circle awaits with its upscale shops and eateries, providing a cosmopolitan contrast to Longboat Key's peaceful charm. Longboat Key is not just a destination; it's an experience that embodies the essence of Florida's Gulf Coast luxury. It's a place where the allure of the beach, the comfort of a private home, and the beauty of untouched nature converge to create an idyllic escape for those in search of a truly refined and restful retreat.
Cultural Attractions in Longboat Key
Longboat Key, Florida, may not be the first destination that comes to mind for a cultural enthusiast, but this serene barrier island on the Gulf Coast offers a unique blend of leisure and cultural experiences. While Longboat Key itself is primarily known for its tranquil beaches and upscale resorts, its proximity to nearby cities like Sarasota provides ample opportunities for arts, history, and local customs exploration. Begin your cultural journey by venturing into Sarasota, known as Florida's Cultural Coast. The Ringling Museum of Art is a centerpiece of the region's art scene, featuring an extensive collection that includes European, American, and Asian art. The museum's grounds also encompass the historic Ca' d'Zan Mansion, a Venetian Gothic palace that was once the home of circus magnate John Ringling, and the Circus Museum, which celebrates the history of the American circus. For live performances, the Sarasota Opera House and the Van Wezel Performing Arts Hall offer a rich calendar of events, from opera and ballet to Broadway shows and symphony concerts. The Asolo Repertory Theatre is another gem, known for its high-quality productions. Art galleries abound in Sarasota's vibrant downtown and the Rosemary District, where you can discover local artists and their works. The Art Center Sarasota and the Sarasota Visual Art Center are hubs for contemporary art exhibitions and workshops. Music lovers will find a thriving live music scene in Sarasota's bars and clubs, with genres ranging from jazz and blues to classical. The Sarasota Orchestra and the Jazz Club of Sarasota are key institutions that regularly host concerts and events. Local customs and history can be explored at the Historic Spanish Point, an outdoor museum in nearby Osprey that offers a glimpse into 5,000 years of Florida history. The Powel Crosley Estate, a 1920s mansion, also hosts various cultural events throughout the year. While Longboat Key itself is a haven for relaxation and beachside enjoyment, it serves as a peaceful base from which to explore the rich cultural offerings of the Sarasota area. Whether you're interested in the visual arts, performing arts, or the history and customs of Florida's Gulf Coast, you'll find a variety of experiences just a short drive from the quiet shores of Longboat Key.
Kids IconFamily friendly activities in Longboat Key
Longboat Key, Florida, is a serene barrier island on the Gulf Coast that offers a tranquil escape for families with children. Its pristine beaches and clear waters provide the perfect backdrop for a variety of kid-friendly activities. Start your adventure on the soft, white sands of Longboat Key's beaches, where children can spend hours building sandcastles, collecting shells, or splashing in the gentle waves. The calm Gulf waters are ideal for introducing little ones to swimming or even trying out snorkeling to explore the underwater world. For a change of scenery, take a short drive to nearby Mote Marine Laboratory & Aquarium. This research facility and public aquarium is a hit with kids, offering close-up encounters with marine life such as sharks, manatees, sea turtles, and a plethora of fish species. Interactive exhibits and touch tanks provide an educational yet fun experience for curious minds. If your family enjoys outdoor activities, consider renting kayaks or paddleboards to explore the calm waters around the key. Paddling along the mangrove tunnels is an enchanting experience, and you might even spot dolphins or manatees if you're lucky. For a leisurely family outing, visit Joan M. Durante Community Park, a peaceful nature park with walking trails, playgrounds, and picnic areas. Children can play amidst the lush greenery while parents relax in the shade of Australian pines. Golfing families will appreciate the island's well-maintained courses, where you can enjoy a round of golf while the kids take lessons or participate in junior golf programs designed to introduce them to the sport. Dining on Longboat Key is a family affair, with many restaurants offering kid-friendly menus and outdoor seating with views of the water. After dinner, treat the kids to a scoop of homemade ice cream at one of the local parlors. For a day trip, consider visiting the nearby Sarasota Jungle Gardens, where children can feed flamingos by hand and watch exciting animal shows. The interactive experiences here are both fun and educational, making it a memorable outing for the whole family. Longboat Key's blend of natural beauty, wildlife encounters, and family-oriented activities make it an ideal destination for those traveling with children. It's a place where families can unwind, bond, and create lasting memories together.
Nature IconOutdoor activities in Longboat Key
Longboat Key, Florida, is a serene barrier island on the Gulf Coast, known for its stunning beaches, lush tropical landscapes, and an array of outdoor activities that nature lovers can revel in. The island's natural beauty provides a tranquil escape for those looking to connect with the environment and enjoy the great outdoors. The beaches of Longboat Key are a highlight, with their soft white sands and clear blue waters. These are perfect for sunbathing, beachcombing, and enjoying the gentle sea breeze. The calm Gulf waters also make for excellent swimming, kayaking, and paddleboarding. Visitors can rent equipment from local outfitters or join guided tours to explore the coastline and nearby mangrove tunnels. For those interested in wildlife, Quick Point Nature Preserve on the southern tip of the island offers a chance to observe native plants and animals in their natural habitat. The preserve features boardwalks and trails that meander through mangrove forests and tidal lagoons, providing opportunities for bird watching and photography. It's not uncommon to spot herons, ospreys, and even the occasional dolphin or manatee. Boating and fishing are also popular activities in Longboat Key. The surrounding waters are teeming with a variety of fish species, making it an angler's paradise. Charter a boat for deep-sea fishing or try your luck in the calmer bay waters. For a more relaxed experience, sunset cruises are available, offering stunning views of the horizon as the sun dips below the Gulf of Mexico. For those who enjoy hitting the links, Longboat Key boasts exceptional golf courses with scenic views and challenging play. The island's courses are surrounded by natural beauty, providing a peaceful backdrop for a round of golf. Nature trails and parks are scattered throughout the island, inviting visitors to take leisurely walks, go for a run, or simply enjoy the local flora and fauna. Biking is another great way to explore Longboat Key, with its well-maintained bike lanes and paths that offer a safe and enjoyable ride with picturesque views. Lastly, no visit to Longboat Key would be complete without experiencing the magical sunsets. Whether you're watching from the beach, a waterfront restaurant, or a private balcony, the vibrant colors reflecting off the Gulf's surface are a breathtaking sight that embodies the natural splendor of Longboat Key. In summary, Longboat Key is a haven for outdoor enthusiasts who cherish the natural world. From its pristine beaches and wildlife preserves to its water sports and sunset views, this Florida gem offers a multitude of ways to connect with nature and find tranquility.
Weather IconWeather in Longboat Key
Longboat Key, Florida, is a serene barrier island on the Gulf Coast, known for its balmy weather and beautiful beaches. The climate here is classified as humid subtropical, which means you can expect warm temperatures year-round, with a distinct wet and dry season. The winter months, from December to February, offer the most comfortable weather, with average high temperatures ranging from the mid-60s to mid-70s Fahrenheit (around 18°C to 24°C). This is the peak season for visitors looking to escape colder climates, as the humidity is lower and rainfall is minimal. Nights can be cooler, so it's wise to pack a light jacket. Spring, from March to May, sees a gradual increase in temperature, with highs typically in the 70s to low 80s Fahrenheit (mid-20s to low 30s Celsius). This is an excellent time to visit Longboat Key, as the weather is warm but not yet at its most humid, and the Gulf waters are becoming pleasantly warm for swimming. Summer, from June to September, is the hottest and most humid time of the year, with temperatures often reaching into the 90s Fahrenheit (mid-30s Celsius). This period also coincides with the rainy season, where afternoon thunderstorms are common, bringing brief but heavy downpours. Despite this, the warm Gulf waters and the allure of sun-soaked beaches make it a popular time for beachgoers. Autumn, from October to November, sees a return to milder weather. The humidity begins to drop, and temperatures settle into the 70s and 80s Fahrenheit (mid-20s to low 30s Celsius). The water remains warm enough for swimming, and the risk of rain diminishes, making it a delightful time to visit. The most popular weather conditions are prevalent during the winter and spring months when the climate is especially pleasant. These seasons offer a perfect blend of warm days and cooler evenings, ideal for enjoying all that Longboat Key has to offer, from its pristine beaches to its upscale dining and leisure activities. For those looking to enjoy the best weather conditions, plan your visit between March and May or from October to December. During these times, you'll experience the island's natural beauty comfortably, with fewer chances of rain and a break from the intense summer heat.
Transportation in Longboat Key
Longboat Key, a serene barrier island on Florida's west coast, offers a tranquil escape with its stunning beaches and upscale amenities. While it may not have the extensive public transportation systems of larger cities, there are still several convenient options for getting to, from, and around this idyllic destination. Most visitors arrive at Longboat Key by car, either driving from nearby cities or renting a vehicle upon arrival at the nearest major airport, Sarasota-Bradenton International Airport, which is about a 20-minute drive from the island. Tampa International Airport is another option, approximately an hour and a half away, offering a wider range of domestic and international flights. Once on Longboat Key, the transportation options are more limited, but there are still ways to navigate the area. The island itself does not have a public bus service, so having a car is the most convenient way to explore at your own pace. This is especially useful for trips to nearby attractions, grocery stores, and restaurants, as well as for visiting neighboring islands like Anna Maria Island or the cultural attractions in Sarasota. For those who prefer not to drive, ride-sharing services like Uber and Lyft are available, as are local taxi companies. Some resorts and vacation rentals offer shuttle services or bicycles for guests to use, which can be a pleasant way to enjoy the island's scenery. Longboat Key is somewhat walkable, particularly if you're staying in a centrally located resort or vacation rental. Many visitors enjoy strolling along the beach or walking to nearby shops and restaurants. However, the island is about 11 miles long, so for longer distances, a car or other transportation method would be necessary. Biking is another popular way to get around Longboat Key. The island has a dedicated bike lane that runs nearly its entire length, making it safe and enjoyable for cyclists to explore. Bike rentals are available, allowing visitors to enjoy the island's natural beauty at a leisurely pace. In summary, while Longboat Key may not have the extensive transportation infrastructure of a major city, it offers enough options to ensure a comfortable and convenient stay. Whether you're driving, biking, or using ride-sharing services, you'll find it easy to relax and enjoy all that this peaceful island has to offer.