TOP 30 Island luxury rentals in Sarasota, Florida

Siestakey-Rental Private Charter Boat Cruise offers a unique and personalized experience as you explore the stunning waters of Siesta Key and Little Sarasota Bay. Our private charters are conducted on a comfortable Hurricaine 188 Deck Boat, complete with ample seating and optional shade. Captain Matt and his wife Diana, both US Coast Guard certified, will ensure a safe and enjoyable journey. Conveniently located near the north bridge of Siesta Key, our private charters offer complimentary public parking for easy access. With a wealth of positive reviews from previous guests, you can trust in our exceptional hospitality and local expertise. As a special touch, we provide photographs from your cruise as a memorable keepsake. Experience the beauty of Siesta Key and Sarasota with Siestakey-Rental Private Charter Boat Cruise.

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.

Siesta Beach Rentals is a premier real estate and travel agency located at 333 Canal Road in Sarasota, Florida. We specialize in offering vacation rentals in the beautiful Siesta Key area, known for its stunning white sand beaches and crystal-clear waters. Our experienced team is dedicated to helping you find the perfect rental property for your next beach getaway, whether you're looking for a cozy condo or a luxurious beachfront villa. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact Siesta Beach Rentals today to start planning your dream beach vacation in Sarasota, Florida.

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.

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.

Welcome to Avis Car Rental at Sarasota/Bradenton International Airport, conveniently located at 6018 Airport Circle, Sarasota, Florida. Whether you're visiting for business or leisure, our wide range of rental vehicles ensures you have the perfect car to explore the vibrant city of Sarasota and the stunning beaches nearby. Special Offer: Enjoy one day free of daily time and mileage charges on rentals of an intermediate (group C) to a full-size four-door (group E) car when you rent for a minimum of three days. Please note that taxes, concession recovery fees, customer facility charges, and fuel charges are extra. Optional items like LDW and other surcharges may also apply. This offer is valid at Avis locations in the contiguous U.S., excluding the New York Metro area, and is subject to availability. Make sure to reserve in advance and provide the profile number associated with your coupon.

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.

Chart House, located at 201 Gulf of Mexico Drive in Longboat Key, Florida, is a top waterfront restaurant offering stunning views of Sarasota Bay. With a relaxing atmosphere both inside the dining room and outside on the terrace, this seafood restaurant is the perfect escape from the daily grind. Enjoy Happy Hour specials daily from 4PM to 6:30PM, as well as early dining hours from 4PM to 6PM. Indulge in delicious seafood specialties with a local twist, or sip on cocktails at the comfortable bar seating. Situated on beautiful Longboat Key, Chart House is a tropical retreat just a short drive away from outdoor destinations like South Lido County Park and Bay Island Park. With boat rentals, bike tracks, and more nearby, this restaurant is the ideal spot for a relaxing getaway. As they reopen their dining rooms, Chart House is committed to ensuring the safety of their guests and looks forward to serving you once again.

Bahamas Sailing Adventures is a premier sailing institution located at 15600 Hancock Road in Sarasota, Florida, United States. With a passion for the sea and a dedication to providing unforgettable sailing experiences, our team of experienced captains and crew members are committed to creating the perfect sailing adventure for all our guests. Whether you are looking for a relaxing day on the water or an exhilarating sailing excursion, Bahamas Sailing Adventures offers a variety of customizable packages to suit your needs. Come sail with us and discover the beauty of the Bahamas from the comfort of our luxurious sailboats.

Gulfside Beach Club is a dream getaway located at 427 Casey Key Road in Nokomis, Florida, United States. Nestled on a unique barrier island on Florida's Gulf Coast, this lodging institution offers a charming and relaxing atmosphere reminiscent of an "old Florida" beach resort. The crisp whitewashed buildings with blue awnings give off a Greek island retreat vibe, while the expansive pristine beach, colorful botanical gardens, and boat docks make Gulfside Beach Club stand out from other resorts in the area. Choose from a variety of accommodations, including one-bedroom beachfront villas, two-bedroom apartments with beach-facing decks, and garden-view apartments. All units are equipped with fully stocked kitchens, washer/dryer, and central AC. Rates start at $375 per day for two people, with additional guests charged at $20/person/night. Rates do not include Florida taxes.

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.

Captiva Beach Resort is a charming boutique lodging option located in the heart of Sarasota, Florida. Situated at 6772 Sarasea Circle, this resort offers a unique blend of relaxation and luxury for guests looking to escape the hustle and bustle of everyday life. With a laid-back beach vibe, Captiva Beach Resort provides comfortable accommodations and a convenient location just steps away from the pristine white sands of the Gulf Coast. Whether you're looking for a cozy room for a weekend getaway or a stylish outfit for a day at the beach, this institution has you covered. Experience the ultimate in seaside relaxation at Captiva Beach Resort.

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.

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.

ALD Limo at SRQ Airport is a top airport limo service provider located at 6006 Airport Circle in Sarasota, Florida. Specializing in luxury sedans and SUVs, ALD Limo offers transportation services to various areas including Sarasota, Siesta Key, Anna Maria Island, and more. Conveniently located at Baggage Claim #3, ALD Limo ensures a seamless check-in process for all passengers. With a focus on reliability and professionalism, ALD Limo's airport car service is the perfect solution for travelers in need of efficient and comfortable transportation. Their punctual drivers and top-notch service make them a highly recommended option for airport transfers. Whether you're a frequent customer or a first-time rider, ALD Limo guarantees a pleasant and stress-free experience. Book your ride today and start your journey to the airport with ALD Limo's on-time, reliable, and courteous service.

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.

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!

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!

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.

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.

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.

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.

OHasis Getaway is a real estate and travel agency located at 211 Elm Avenue in Anna Maria, Florida, United States. Just steps away from the stunning Gulf side beaches of Anna Maria Island, our locations are perfect for a relaxing escape. We take pride in providing Midwestern care to ensure your OHasis Getaway is prepared for you to simply enjoy island life. Our properties offer luxurious comfort in soothing island style, allowing you to unwind and recharge. With beautiful sunrises and sunsets, lush flora, and soft sugar sand beaches, you'll feel like you're in paradise. Enjoy amenities such as private pools, outdoor grills, entertainment systems, and fully stocked kitchens with Starbucks coffee beans provided.

Fun Boat Tours is a travel agency located at 1265 Old Stickney Point Road in Sarasota, Florida, United States. We offer a variety of boat tours, including sunset cruises, dolphin watching, private charters, and custom tours. Our tours depart from both Siesta Key Marina and Anna Maria's Keyes Marina, providing you with the opportunity to explore the beautiful waters of the area. Whether you're looking to relax and watch dolphins play, enjoy a stunning sunset, or customize your own adventure, Fun Boat Tours has something for everyone. Join us for an unforgettable experience on the water!

Seas the Day Charters US is a premier travel agency located at 154 Sunaire Terrace in Nokomis, Florida, United States. Our custom Calcutta 263 Sport Catamaran, known as the "Manta", is one of only 7 made with the unique "Slashback" planing hull design. Boats from Calcutta Marine are wood-free and constructed with all composite materials for a sleek and comfortable experience on the water. Captain John Gerhardt, a U.S. Coast Guard Licensed Master Captain with 50 GRT Coastal certification, leads our charters. With a lifelong passion for the water, Captain John grew up on the offshore islands of Siesta and Casey Keys in Sarasota Bay, honing his skills in swimming, sailing, and fishing.