TOP 30 Island vacation rentals in Sarasota, Florida

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Home2 Suites by Hilton Nokomis Sarasota Casey Key is a modern and stylish lodging option located at 227 Albee Road West in Nokomis, Florida. This hotel offers comfortable suites with fully equipped kitchens, spacious living areas, and complimentary Wi-Fi. Guests can enjoy amenities such as a fitness center, outdoor pool, and complimentary breakfast. The convenient location near Casey Key and Sarasota makes it a great choice for both leisure and business travelers looking for a relaxing stay in the Sunshine State.

My Sarasota Getaway is a charming lodging institution located at 119 South Tamiami Trail in Nokomis, Florida, United States. Situated in the beautiful Sarasota area, this getaway offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a home away from home for visitors. With its convenient location and welcoming atmosphere, My Sarasota Getaway is the perfect place to unwind and enjoy all that this picturesque region has to offer. Whether you're looking for a weekend getaway or an extended stay, this institution is sure to provide a memorable experience for all.

ABC Baby and Beach Equipment Rentals is a premier rental service located at 2239 15th Street in Sarasota, Florida. We specialize in providing high-quality baby supplies and beach gear for rent in Sarasota, Siesta Key, Lakewood Ranch, Anna Maria Island, and Bradenton. Our delivery and pick-up process is convenient and hassle-free, with deliveries made before standard check-in times and returns scheduled after check-out. We offer free delivery on orders over $150 to most zip codes, with no additional service charges.

BabyQuip Baby and Beach Rentals - LeAnn Adams is a clothing store located at 4560 Overlook Drive Northeast, St. Petersburg, Florida, United States. Rent baby gear from LeAnn Adams in Parrish, Florida and enjoy convenient pick up and return options at predetermined locations in Tampa Bay, Saint Pete, Clearwater, Anna Maria Island, Holmes Beach, Bradenton Beach, and Sarasota. Customers have praised LeAnn for being prompt, accommodating, and accessible. Contact LeAnn Adams directly through the form on the website or by calling or texting (407)496-9980 for immediate assistance. Please note that specific times are not guaranteed, but your provider will confirm once your reservation has been placed.

The Lido Islander is a premier institution located at 528 South Polk Drive in Sarasota, Florida. As a multi-faceted establishment, it serves as a lodging facility, real estate agency, and travel agency all in one. Whether you are looking for a luxurious place to stay, seeking to invest in property on Lido Key, or planning your next vacation, the Lido Islander offers a one-stop solution for all your needs. With a prime location in the beautiful city of Sarasota, the Lido Islander provides top-notch services and accommodations to ensure a memorable experience for all guests and clients.

Suntide Island Beach Club is a charming beachfront lodging institution located at 850 Benjamin Franklin Drive in Sarasota, Florida, United States. This tropical oasis offers guests a relaxing and rejuvenating stay with its cozy accommodations and stunning views of the Gulf of Mexico. The resort features a variety of amenities including a heated outdoor pool, beach access, BBQ grills, and complimentary Wi-Fi. Whether you're looking to unwind on the sandy shores, explore the local attractions, or simply soak up the sun, Suntide Island Beach Club is the perfect destination for your next vacation getaway.

Lucky Vacation Homes is a premier real estate agency located at 1901 Hyde Park Street in Sarasota, Florida. Our team of experienced professionals are dedicated to helping you find the perfect vacation home for your next getaway. Whether you're looking for a beachfront property, a cozy cabin in the mountains, or a luxurious villa in a tropical paradise, we have a wide variety of options to suit your needs. With our expertise and personalized service, we strive to make your vacation rental experience as seamless and enjoyable as possible. Contact us today to start planning your dream vacation!

Coco Plum of Longboat Key Vacation Home Rental is a real estate and travel agency located at 690 Penfield Street in Longboat Key, Florida, United States. This amenity-packed 2-bedroom, 2-bathroom vacation rental offers a quiet and serene location, a fully equipped kitchen, multiple balconies with lounge furniture, and a patio with hammock swings for ultimate relaxation. Guests can rent a boat or bring their own to park at the on-site canal-front boat dock. Enjoy reading by the pool or sipping a drink on the beach during your month-long getaway. Explore the surrounding area by sea, with attractions such as Cannons Marina, Beer Can Island, and Siesta Key within easy reach. On land, visit Leffis Key Preserve, Portosueno Park, and Robinson Preserve for outdoor adventures. Nearby attractions include the Beach Market at Coquina Beach, the Florida Maritime Museum, and Downtown Sarasota.

Vacation Rentals Lido Key is a premier real estate and travel agency located at 722 South Boulevard of the Presidents in Sarasota, Florida. Specializing in luxurious vacation rentals on Lido Key, this agency offers a wide range of stunning properties for travelers looking for the perfect beach getaway. From cozy condos to spacious beachfront homes, Vacation Rentals Lido Key has something for everyone. With top-notch customer service and a passion for providing unforgettable vacation experiences, this agency is your go-to destination for planning your next trip to Sarasota. Book your dream vacation rental with Vacation Rentals Lido Key and make memories that will last a lifetime.

Lido Key Vacations is a premier real estate and travel agency located in Sarasota, Florida. Our team of experienced professionals is dedicated to helping you find the perfect vacation rental or property on beautiful Lido Key. Whether you're looking for a luxurious beachfront villa or a cozy bungalow, we have a wide range of options to suit your needs. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Visit us at 5231 Avenida Navarra and let us help you plan your dream getaway to paradise.

Siestakey-Rental Vacation Rentals is a real estate and travel agency located at 202 Island Circle in Siesta Key, Florida. This exclusive property, Siesta Key Heritage House, is now available for reservations for Christmas 2024, with limited availability in 2025. The house is situated in the private Palm Island enclave just 2.5 blocks away from the world famous Siesta Key Beach. Guests can enjoy modern luxuries in a home that pays homage to the early Sarasota Bayfront hotels. The property features a waterfront pool, jacuzzi, porches, and a private dock for fishing or launching stand-up paddle boards. The chef's kitchen is fully equipped for entertaining up to 20 guests. Reservation inquiries can be made by contacting Siestakey-Rental at 941-363-1216 or siestakeyheritagehouse@gmail.com. Enjoy a luxurious and secluded getaway at Siesta Key Heritage House.

Island Time Charter is a unique establishment located on 11th Street in Sarasota, Florida, United States. This dual-purpose venue serves as both a bar and a travel agency, offering patrons the opportunity to enjoy a refreshing drink while planning their next adventure. Whether you're looking to unwind with a cocktail or book a thrilling excursion, Island Time Charter has you covered. With a laid-back atmosphere and friendly staff, this is the perfect place to kick back and relax while making plans for your next getaway.

Robin Hood Rentals Siesta Key is a premier store located at 5255 Ocean Boulevard in Sarasota, Florida. Specializing in providing top-quality rental services for visitors looking to explore the beautiful Siesta Key area, this institution offers a wide range of rental options including bicycles, kayaks, paddleboards, beach chairs, umbrellas, and more. With a convenient location and friendly staff, Robin Hood Rentals Siesta Key is the perfect destination for those looking to make the most of their time in this stunning beachside community.

Welcome to Island Tides Vacation Rental, your premier destination for unforgettable getaways on the stunning Gulf Coast. Located at 1110 Via De Luna Drive, Pensacola Beach, Florida, our business combines the expertise of a real estate and travel agency to offer you the finest selection of vacation properties. Whether you're seeking a serene escape or a family adventure, we have the perfect accommodations to suit your needs. Explore our diverse portfolio of 33 meticulously curated properties, each offering unique experiences and luxurious amenities. From the pet-friendly charm of Aloha by the Sea, with its breathtaking views and wrap-around porch, to the opulence of Aqua Palms, featuring a private heated pool and spacious lawn, your ideal vacation home awaits.

Gulf Sands Beach Resort is a charming lodging institution located at 433 Casey Key Road in Nokomis, Florida, United States. Situated between Sarasota and Venice, this resort offers guests a beautiful beach and stunning sunsets in a relaxing Old Florida environment. The resort is located on Casey Key, a unique barrier island directly on the Gulf of Mexico, just north of Venice. Accommodations at Gulf Sands Beach Resort include one and two-bedroom apartments, each featuring equipped kitchens, full baths, bedrooms, living rooms, and dining areas. Guests can enjoy the 'Old Florida' ambiance with their toes in the sand and a drink in hand while taking in the spectacular views.

Venice Beach Villas is a lodging institution located at 501 West Venice Avenue in Venice, Florida, United States. Situated on the beautiful Island of Venice, our condo rentals are just a short walk from the Venice Public Beach and the charming historic downtown Venice shops and restaurants. The location of Venice Beach Villas makes it a perfect choice for those looking to explore the surrounding areas, with Sarasota to the north and Englewood, North Port, and Port Charlotte to the south. Our institution is committed to providing a comfortable stay for all guests, including those with disabilities. While the building has limited accessibility features due to its age, we strive to accommodate and assist all customers to the best of our ability.

The Inn at Turtle Beach is an award-winning and nationally recognized lodging located at 9004 Midnight Pass Road in Sarasota, Florida. Our resort offers a peaceful and secluded retreat with beautiful views of Little Sarasota Bay and is just minutes away from Turtle Beach. Each cottage and suite features a private enclosed patio with a hot tub and hammock, perfect for relaxation. Guests can also enjoy private docks with stunning water views. Book directly with us for the best rates and availability by calling 941 349 4554 or clicking our website link. Experience Siesta Key in its true tropical beauty at the Turtle Beach Resort. With lush gardens, water views, beach access, and a private courtyard, our resort is the perfect getaway. Located on Little Sarasota Bay, we are just a short walk to Turtle Beach. Relax in your private hot tub, lounge in a hammock, take a kayak tour, or enjoy our heated pool. The possibilities for relaxation and fun are endless.

Captain Fin's Sightseeing and Boat Tours is a popular tourist attraction and travel agency located at 1325 Gulf Drive South in Bradenton Beach, Florida, United States. Specializing in sunset cruises, dolphin excursions, sandbar trips, shelling adventures, and Egmont Key charters, Captain Fin's offers a unique way to explore the beautiful intercoastal waterways of Anna Maria, Longboat Key, and Sarasota Bay. With over 45 years of experience on the waters of Anna Maria Island and Tampa Bay, Captain Fin's ensures a memorable and enjoyable experience for all guests. Don't miss the opportunity to relax and watch the stunning sunset while sipping on your favorite beverage, or to collect shells along the secluded beaches of Egmont Key. Book your sightseeing and boat tour with Captain Fin's today for an unforgettable adventure on the waters of Florida's Gulf Coast.

Cartier Limousine Services is a premier transportation company located at 6514 13th Avenue Drive West in Bradenton, Florida. We specialize in providing luxurious limo, transfers, and shuttle services to Anna Maria Island, Bradenton, Tampa, and Sarasota airports. Our team ensures safe and reliable transportation to and from various local airports, including Tampa, Sarasota, and Orlando. We prioritize communication with our clients and their chosen airlines to guarantee prompt and timely pickups. Our experienced drivers are familiar with the area's airports and go above and beyond to coordinate your travel seamlessly. We offer tips for booking transportation services to and from Anna Maria Island and surrounding areas, ensuring a stress-free experience for our customers. Additionally, we provide special assistance for handicapped travelers, minors, and those with language barriers.

Turtle Crawl Inn Resort is a beachfront paradise located at 4235 Gulf of Mexico Drive, Longboat Key, Florida. Offering easy living on the Gulf Coast, this resort features vacation beach condos near Sarasota, Florida. With a variety of room styles including accommodations at The Towers, The Gardens, and The Villas, guests can enjoy plush island luxury and quiet pleasures that cater to all personalities. The resort has 20 units directly facing the beautiful Gulf of Mexico, all with one bedroom, one bathroom, and a studio apartment style living area with a balcony overlooking the beach. Most units include a sleeper sofa and can accommodate up to 6 people. Guests can enjoy the heated pool, barbecue area, putting green, shuffleboard area, and easy access to the beach. The resort offers clean and comfortable rental condominiums and villas with fully equipped kitchens. Visitors can partake in activities such as shelling, biking, fishing, watersports, and dining, or simply relax on the white sand beaches and enjoy the warm Sarasota sun. With excellent views of the water and spectacular sunsets, Turtle Crawl Inn Resort is the perfect choice for a Longboat Key vacation. Previous guests have praised the resort for its friendly staff, peaceful atmosphere, and private beach access, making it a top choice for a relaxing getaway.

Rent The Keys is a lodging, real estate, and travel agency located at 3018 Gulf Drive in Holmes Beach, Florida. Start your vacation now by booking Florida Keys luxury vacation rentals through RentTheKeys.com. Discover the value and savings of staying in vacation rental homes or condominiums with amenities such as heated pools, gourmet kitchens, and custom-designed properties on the best beaches in the world. Explore the various keys on the Gulf Coast of Florida, including Siesta Key, Anna Maria Island, Lido Key, Longboat Key, and Casey Key. Experience island living on Anna Maria Island and Siesta Key with miles of white sandy shores and crystal-clear waters. RentTheKeys also offers Sarasota Florida Keys vacation rentals.

Tropical Sands Accommodations is a premier real estate and travel agency located at 5231 Avenida Navarra in Sarasota, Florida. Specializing in luxurious beachfront properties and vacation rentals, we offer a wide range of accommodations to suit every traveler's needs. Whether you're looking for a cozy beach cottage or a spacious oceanfront villa, our team of experienced agents is dedicated to helping you find the perfect tropical getaway. With stunning views, top-notch amenities, and personalized service, Tropical Sands Accommodations is your go-to destination for a truly unforgettable vacation experience in the Sunshine State. Book your dream beach retreat with us today!

Marganon Real Estate Firm is a premier real estate agency located at 1845 East West Parkway in Fleming Island, Florida. Specializing in properties in Jacksonville and Sarasota communities, our firm offers a state-of-the-art property search tool with an interactive map feature to help you find your dream home in Jacksonville, FL. Our listings are updated daily from the MLS, ensuring you have access to the latest properties on the market. Explore the diverse neighborhoods and communities in Jacksonville with the help of our Community Guide, which will keep you informed about the newest properties in the areas you are interested in. Register for a free account to receive email notifications whenever new homes that match your criteria become available, and save your favorite properties for quick and easy access.

The Cottages at Siesta Key is a charming resort located at 1105 Point of Rocks Road in Sarasota, Florida. This unique beach cottage experience is just a short walk from the white, powdery sand and aquamarine waters of Siesta Key Beach. We have been awarded the TripAdvisor Certificate of Excellence in both 2017 and 2018, and offer 13 individually decorated cottages ranging from studio size to 4 bedrooms. Our amenities include full kitchens, private decks, barbecue grills, and a pool. Whether you're planning a romantic getaway, family vacation, reunion, or wedding, The Cottages at Siesta Key is the perfect choice. We are just steps from the beach and close to a variety of activities, including dining, scuba diving, shopping, dolphin watching, fishing, and parasailing. Book your stay with us today and experience the difference at The Cottages at Siesta Key.

Florida Dream Home Team - Coldwell Banker Realty is a premier real estate agency located at 8334 Market Street in Bradenton, Florida, United States. Specializing in properties in the vibrant community of Lakewood Ranch, which is home to over 55,000 residents and 1,841 jobs, our team offers expertise in buying and selling homes in this desirable area. Lakewood Ranch boasts A-rated schools, town centers, golf courses, and the Lakewood Ranch Medical Center, making it an ideal place to live. Additionally, we also serve the beautiful barrier island of Longboat Key, known for its stunning beaches and mangroves. Sarasota, with its unique arts scene and beachy atmosphere, is another area we cover, along with the popular Siesta Key, home to the award-winning Siesta Public Beach. Whether you are looking for a vacation home, investment property, or your dream residence, our team can help you find the perfect property. Visit us today to access full property details and exclusive listings. Prices and inventory are current as of April 6, 2024. To continue your property search, agree to our Terms of Use.

Escape to paradise at our beach bungalow on Siesta Key, located at 303 Canal Road in Sarasota, Florida. This charming real estate and travel agency offers a unique opportunity to experience the beauty and tranquility of one of the most stunning beaches in the United States. Our bungalow provides the perfect blend of comfort and luxury, with easy access to the crystal-clear waters and white sandy beaches of Siesta Key. Whether you're looking for a relaxing getaway or a fun-filled adventure, our beach bungalow is the ideal destination for your next vacation. Book your stay with us today and discover the magic of Siesta Key.

The Best House on Siesta Key Beach & Village is a unique vacation rental agency located at 5230 Calle Menorca in Sarasota, Florida. Our one-of-a-kind vacation homes offer guests the perfect blend of privacy and luxury, with all the amenities needed for a fabulous Florida beach vacation. Each property is custom designed by local artists, providing a true taste of the Florida lifestyle. Situated on the eight-mile-long Siesta Key, our properties are just steps away from the world-famous Siesta Key Beach, ranked as the #1 Beach in the U.S. in 2020. Guests can enjoy the shallow waters, year-round lifeguard patrol, and a variety of outdoor activities such as sailing, fishing, kayaking, and more.

Charlotte House is a charming lodging option located at 302 East Charlotte Avenue in Punta Gorda, Florida. This small bungalow has an open floor plan that makes it feel larger than its 750 square feet. With 2 bedrooms, Charlotte House can comfortably sleep 5 guests in beds - one room with a queen bed, another with two twin beds, and a bonus room with a daybed. Situated in the historic town of Punta Gorda on Charlotte Harbor, where the Peace River meets the Gulf of Mexico, Charlotte House offers easy access to wonderful restaurants, cocktails, and stunning sunsets. The town is centrally located between two famous beaches - Siesta Key in Sarasota to the north and Sanibel Island to the south. Outdoor enthusiasts will enjoy activities such as boating and fishing, as well as beautiful parks and pickleball courts along the Harbor. Punta Gorda also hosts a variety of events throughout the year, including block parties, wine and jazz festivals, and dragon boat races.

Sharkey's Glass Bottom Tours is a travel agency located at 4237 Gulf Boulevard in St. Pete Beach, Florida. They offer the original and only Glass Bottom Kayak LED illuminated Fish Feeding Night Tours, providing an unforgettable experience at various locations throughout Florida. The tours take place from sunset to night at 8pm and a full dark night tour at 9:30pm, allowing guests to illuminate the sea-floor while viewing sea-life up close. Visitors can explore the Nature Preserve & Mangrove Tunnels, relax on sandbars, and enjoy snorkeling with the provided equipment. The institution also offers Daytime Island & Mangrove Tunnel Adventures where dolphins and manatees are often spotted. With locations in St. Pete Beach, Clearwater Beach, Sarasota, and West Palm Beach, Sharkey's Water Sports is known for its unique tours that attract sea-life with high powered underwater LED lights. Guests have raved about their experiences, praising the knowledgeable guides, calm waters, and the opportunity to interact with marine life. Whether you're looking for a fun family outing or a romantic date night, Sharkey's Glass Bottom Tours offers a memorable adventure for all ages.

Anna Maria Yacht Charters LLC is a premier travel agency located at 4208 129th Street West, Cortez, Florida, United States. Known as the region's most reliable and fun boat charters, they offer an unforgettable experience cruising the waters from Anna Maria Island to Sarasota Bay. With a maximum capacity of 6 passengers, their yacht certified boat provides ample room and comfortable seating for guests to enjoy a variety of activities. From dolphin tours with occasional manatee sightings to island hopping adventures, Anna Maria Yacht Charters LLC offers a customizable experience tailored to enhance your time on the water. Guests can enjoy snorkeling at Egmont Key, exploring Passage Key's pristine waters, and relaxing on the beautiful beaches of Jew Fish Key.