TOP 30 Island luxury rentals in Florida

Island Real Estate of Anna Maria Island, Inc. is a premier real estate and travel agency located at 6101 Marina Drive, Holmes Beach, Florida, United States. Specializing in vacation rentals on the beautiful Anna Maria Island, our agency offers a wide range of beachfront properties with stunning views of the Gulf of Mexico. With over 50 years of experience, our dedicated staff is committed to providing top-notch customer service and ensuring that every guest has a relaxing and memorable stay. From cozy beachfront cottages to luxurious oceanfront mansions, we have the perfect rental for every taste and budget. Our team of local experts are available 24/7 to assist with any questions or concerns, and can provide recommendations for the best local spots and experiences to enjoy during your stay. Whether you're looking for a quick getaway or a long-term investment, Island Real Estate has you covered. Book your Anna Maria Island rental today and experience the beauty and charm of Florida's hidden gem.

Cindy Quinn PA is a renowned real estate professional at Sato Real Estate, located on Anna Maria Island in Florida. With over 25 years of experience, Cindy is consistently ranked in the top 1% of Florida Realtors and holds prestigious designations such as the Million Dollar GUILD and Certified Luxury Home Marketing Specialist. Her strong work ethic, integrity, and passion for helping clients achieve their real estate goals have earned her a stellar reputation in the industry. Specializing in the Anna Maria Island and Bradenton communities, Cindy is well-connected and has a deep understanding of the local market trends, schools, and political issues that impact real estate. She is committed to providing superior client service with attention to detail, urgency, and a reputation for quality and kindness that clients can rely on.

The Palm Tree Vacation Rental is a luxurious real estate and travel agency located at 818 Eagle Lane in the beautiful Apollo Beach, Florida. We offer a wide range of vacation rentals, from cozy beachfront condos to spacious villas with stunning views of the ocean. Our dedicated team is committed to providing exceptional service and helping you find the perfect accommodation for your next getaway. Whether you're looking for a relaxing beach retreat or an action-packed adventure, The Palm Tree Vacation Rental has something for everyone. Book your dream vacation today and experience the ultimate in comfort and relaxation.

MAA Harbour Island is a premier real estate agency located at 800 Harbour Post Drive in Tampa, Florida. Our dedicated team of professionals specializes in helping clients buy, sell, and rent properties in the beautiful Harbour Island neighborhood. With a focus on personalized service and attention to detail, we strive to make the real estate process seamless and stress-free for our clients. Whether you are looking for a luxury waterfront property or a charming condo in the heart of the city, MAA Harbour Island is here to help you find your dream home. Contact us today to learn more about our services and how we can assist you with all of your real estate needs.

Island Villas Apartments is a premier residential community located at 121 Danube Avenue in Tampa, Florida. Our luxurious apartments offer a perfect blend of comfort and style, with spacious floor plans and modern amenities. Residents can enjoy beautiful views of the surrounding landscape and access to a range of on-site facilities, including a swimming pool, fitness center, and clubhouse. Situated in a prime location in Tampa, Island Villas Apartments provides easy access to shopping, dining, and entertainment options. Experience upscale living at its finest at Island Villas Apartments.

Islander Properties Inc. is a versatile institution located at 330 South Gulf Boulevard in Placida, Florida. As a general contractor, real estate agency, and travel agency all rolled into one, we offer a wide range of services to meet your needs. Whether you're looking to build your dream home, buy or sell property, or plan your next vacation getaway, our experienced team is here to assist you every step of the way. Trust Islander Properties Inc. for all your construction, real estate, and travel needs in the beautiful state of Florida.

Boca Grande Club Rentals is a premier vacation rental destination located at 5000 Gasparilla Road in Boca Grande, Florida. Offering luxurious accommodations and top-notch amenities, guests can enjoy a relaxing and unforgettable stay on this beautiful island. With access to pristine beaches, a private golf course, tennis courts, and a variety of dining options, Boca Grande Club Rentals is the perfect choice for those seeking a high-end vacation experience. Whether you're looking for a romantic getaway, a family vacation, or a corporate retreat, this institution provides everything you need for a memorable stay in paradise.

Grace River Island Resort is a hidden gem located at 14524 Riverside Drive in Fort Myers, Florida. This private tropical island vacation home is nestled on the Caloosahatchee River, accessible via a land bridge that transforms it into a peninsula. Whether you are looking for a memorable family vacation, a romantic honeymoon, an intimate wedding venue, or simply some time away, Grace River Island Resort offers the perfect setting. The resort features a spacious 6-bedroom, 8-bathroom house that can accommodate up to 20 guests, making it ideal for family reunions or group getaways. Guests can enjoy a large air-conditioned bonus room, a 2000 sq ft deck overlooking the river with market lighting, a heated swimming pool, a beautiful gazebo, an upscale courtyard, and a grassy point with stunning sunsets. The bridal suite upstairs is perfect for wedding preparations, while the groomsman area downstairs provides a space for the guys to relax before the ceremony.

Sanibel Island Vacation Condo Rental is a premier real estate and travel agency located at 5117 Sea Bell Road in beautiful Sanibel, Florida. We offer a variety of luxurious vacation condo rentals for visitors looking to experience the ultimate island getaway. Our properties are conveniently located near the beach, shopping, dining, and other attractions, making it easy for guests to explore all that Sanibel has to offer. Whether you're looking for a romantic retreat, a family vacation, or a solo adventure, our team is dedicated to helping you find the perfect accommodations for your stay. Book with us today and start planning your dream vacation on Sanibel Island!

Sanibel Island Condo Rentals at Blind Pass offers beautiful and spacious accommodations in a tropical paradise. Located at 5117 Sea Bell Road in Sanibel, Florida, this institution provides guests with a peaceful and luxurious retreat. With easy access to the stunning beaches of Sanibel Island and the amenities of Blind Pass Condominiums, visitors can relax and unwind in style. Whether you're looking for a romantic getaway, a family vacation, or a solo escape, Sanibel Island Condo Rentals at Blind Pass has the perfect accommodations for your needs. Enjoy the beauty of the island and all it has to offer from the comfort of your own private condo.

Sundial Gulf Front Vacation Rentals offers two luxurious units, K405 and A303, located at 1501 Middle Gulf Drive in Sanibel, Florida. Unit K405 boasts stunning Gulf views, two bedrooms, two bathrooms, a spacious living room, dining room, and den. The master suite features a king bed and double sink, with sliding glass doors leading to a screened lanai just steps away from the white sandy beach. Unit A303 offers one bedroom with a king bed, one bathroom, and an open floor plan living/dining room with direct Gulf views. Both units come equipped with a fully-equipped kitchen, beach chairs, pool towels, WiFi, and more. Enjoy amenities such as free adult bikes, a beachfront heated swimming pool, BBQ gas grills, and more at the Sundial complex. Rent directly from the reputable management company for a comfortable and carefree vacation experience. Contact Marjorie and Vincent DePrez at 866-291-0031 for more information and to book your stay. Save 30-50% over resort prices and avoid third party "service fees" by booking directly through Sundial Gulf Front Vacation Rentals.

Sanibel Arms Rental B-1 is a real estate agency located at 805 East Gulf Drive in Sanibel, Florida, United States. This institution offers a variety of rental properties in the beautiful Sanibel area, including the spacious and well-appointed B-1 unit. With stunning views and convenient access to the beach, Sanibel Arms Rental B-1 is the perfect choice for those looking for a relaxing and luxurious vacation rental experience. Whether you are looking for a weekend getaway or an extended stay, Sanibel Arms Rental B-1 has something for everyone. Book your stay today and experience the beauty of Sanibel Island in style.

Kingfisher Vacation Rentals offers a wide range of vacation rentals on the beautiful Sanibel and Captiva Islands in Florida. Located at 2402 Palm Ridge Road, Sanibel, this real estate and travel agency provides luxurious accommodations for visitors looking to experience the stunning beaches and natural beauty of the Gulf Coast. Whether you're looking for a cozy beachfront cottage or a spacious waterfront villa, Kingfisher Vacation Rentals has the perfect option for your island getaway. With personalized service and local expertise, they are dedicated to helping you make the most of your vacation in paradise.

VIP Vacation Rentals in Sanibel is a premier real estate and travel agency located on Periwinkle Way in beautiful Sanibel, Florida. Specializing in luxury vacation rentals, our team is dedicated to providing top-notch customer service and helping you find the perfect accommodations for your next getaway. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious condo, we have a wide variety of options to suit your needs. Let us help you plan the ultimate vacation experience on this idyllic island paradise.

Sanibel Vacations - Island Vacation Rentals is a real estate and travel agency located at 2330 Palm Ridge Road in Sanibel, Florida, United States. They offer a variety of high-quality vacation rentals on Sanibel Island, perfect for a relaxing getaway. Following Hurricane Ian, their properties have been repaired and are ready for rentals in 2023. Whether you're looking for a classic beach cottage, a spacious pool home, or a private retreat near the beach, Sanibel Vacations has something for everyone. With updated furnishings, modern amenities, and beautiful decor, their rentals provide the perfect escape for your next vacation. Book your stay with Sanibel Vacations and experience the beauty of Sanibel Island in style.

Sanibel Captiva Island Vacations is a premier real estate and travel agency located at 11513 Andy Rosse Lane in Captiva, Florida. Our guests enjoy free, exclusive access to the amenities at ‘Tween Waters Island Resort & Spa. We offer professionally-cleaned vacation homes with 24/7 guest support for worry-free travel experiences. With the guaranteed best rates on our vacation rentals, you can stay for four days, four months, or even four seasons - vacation your way. If you're considering becoming a vacation rental homeowner, look no further than Sanibel Captiva Island Vacations. As part of Sanibel Captiva Beach Resorts, a trusted name in Southwest Florida lodging management since 1931, we offer top-rated resorts and exceptional service. Our portfolio includes vacation rentals, restaurants, entertainment venues, marinas, spa services, and recreational activities for all to enjoy. Book your dream vacation with us today!

VIP Vacation Rentals - Captiva is a premier real estate and travel agency located on the stunning Captiva Island in Florida. Situated at 14970 Captiva Drive, this institution offers a wide range of luxurious vacation rentals for those looking to experience the ultimate getaway in paradise. With top-notch customer service and an extensive selection of properties to choose from, VIP Vacation Rentals - Captiva is the perfect choice for anyone seeking a memorable and unforgettable vacation experience. Whether you're looking for a beachfront villa or a cozy cottage, this agency has something for everyone. Book your dream vacation today with VIP Vacation Rentals - Captiva and make your trip to Florida truly special.

Island Vacations of Sanibel & Captiva is a premier real estate and travel agency located on the beautiful islands of Sanibel and Captiva in Florida, United States. With a prime location at 1101 Periwinkle Way, this institution offers a wide range of vacation rental properties, from cozy beachfront condos to luxurious waterfront estates. Their team of experienced agents are dedicated to helping visitors find the perfect accommodation for their island getaway, ensuring a memorable and relaxing vacation experience. Whether you're looking for a romantic retreat or a family-friendly beach escape, Island Vacations of Sanibel & Captiva has something for everyone. Book your dream vacation today and discover the beauty of these enchanting islands.

Sanibel Island Condos is a premier real estate and travel agency located at 979 East Gulf Drive in Sanibel, Florida, United States. We specialize in offering luxurious and comfortable condo rentals on the beautiful Sanibel Island. Our condos are fully equipped with modern amenities and offer stunning views of the Gulf of Mexico. Whether you are looking for a relaxing beach vacation or a romantic getaway, Sanibel Island Condos has the perfect accommodation for you. Our friendly and knowledgeable staff are dedicated to ensuring that your stay is unforgettable. Book your stay with us today and experience the beauty and tranquility of Sanibel Island.

Sanibel Vacation Rentals & Sales is a reputable real estate agency located at 210 Periwinkle Way in Sanibel, Florida, United States. Specializing in vacation rentals and sales, this institution offers a wide range of properties for those looking to experience the beauty of Sanibel Island. With a dedicated team of professionals, Sanibel Vacation Rentals & Sales provides exceptional service and expertise to help clients find the perfect vacation rental or investment property. Whether you are looking for a beachfront condo, a cozy cottage, or a luxurious estate, this agency has something for everyone. Experience the ultimate vacation experience in Sanibel with the help of Sanibel Vacation Rentals & Sales.

Pine Island Vacation Rental Homes is a premier real estate and travel agency located at 5459 Pine Island Road in Bokeelia, Florida. Our agency specializes in providing luxurious vacation rental homes on the beautiful Pine Island. Whether you are looking for a relaxing beachfront villa or a cozy cottage nestled in the tropical landscape, we have the perfect accommodations for your getaway. Our team of experienced professionals is dedicated to ensuring that your vacation experience is unforgettable. Book your dream vacation rental with Pine Island Vacation Rental Homes today and let us help you create lasting memories in paradise.

Green Tortuga Vacation Rental Home is a luxurious real estate and travel agency located at 4511 Cutlass Drive in Captiva, Florida, United States. Offering two exquisite properties, Green Tortuga and Tortuga Sunset, guests can experience the ultimate vacation getaway on North Captiva Island. The spacious open floor plans, private pools, and hot tubs provide a serene and luxurious atmosphere for up to 10 guests. North Captiva Island is a hidden gem, offering pristine beaches, lush vegetation, and remarkable wildlife. Accessible only by boat or small plane, this barrier island provides a tranquil escape from the hustle and bustle of everyday life. Guests can enjoy the beauty of nature, go birdwatching, shelling, or simply relax on the white sand beaches.

Kingfisher Vacation Rentals is a premier real estate and travel agency located at 11528 Andy Rosse Lane in Captiva, Florida. Specializing in luxury vacation rentals, Kingfisher offers a wide selection of stunning properties for visitors looking to experience the beauty of Captiva Island. From beachfront villas to cozy cottages, their expert team is dedicated to helping guests find the perfect accommodation for a memorable getaway. With top-notch customer service and local expertise, Kingfisher Vacation Rentals is the go-to destination for those seeking a truly unforgettable vacation experience in sunny Florida.

Florida Rental Group is a reputable real estate and travel agency located at 1020 Pine Island Road in Cape Coral, Florida. Specializing in vacation rentals, property management, and real estate sales, we offer a wide range of services to meet all of your rental and vacation needs. Our experienced team is dedicated to providing top-notch customer service and helping you find the perfect rental property or vacation home in the beautiful state of Florida. Contact us today to start planning your dream vacation or to inquire about our real estate services.

Island Winds Condominiums is a stunning beachfront property located at 6610 Estero Boulevard in Fort Myers Beach, Florida. As a real estate agency and travel agency, we offer luxurious condominiums for sale or rent, perfect for those looking for a relaxing vacation or a permanent waterfront residence. Our prime location provides breathtaking views of the Gulf of Mexico and easy access to the beach. With top-notch amenities and a friendly staff, Island Winds Condominiums is the perfect destination for your next getaway or investment opportunity.

Tortuga Sunset Vacation Rental is a luxurious real estate and travel agency located at 4540 Seair Lane in Captiva, Florida, United States. Offering two exquisite properties, Green Tortuga and Tortuga Sunset, guests can enjoy a tranquil and luxurious vacation experience on the idyllic North Captiva Island. With spacious open floor plans, private pools, hot tubs, and the option to enhance your stay with an exclusive Island Club Membership add-on, Tortuga Sunset Vacation Rental provides the perfect escape for groups of up to 10 guests. North Captiva Island is a hidden gem, offering pristine white sand beaches, lush vegetation, and remarkable opportunities for birdwatching and shelling. Accessible only by boat or small plane, this barrier island provides a secluded and intimate atmosphere for nature lovers and vacation-goers alike. Visitors can also witness sea turtles during turtle season, making North Captiva Island a must-visit destination for conservationists and wildlife enthusiasts.

Islander Realty is a reputable real estate agency located in the beautiful beach town of Captiva, Florida, United States. Specializing in luxury properties, waterfront homes, and vacation rentals, our experienced team of agents is dedicated to helping clients find their dream homes or investment properties in this stunning coastal area. With a deep knowledge of the local market and a commitment to exceptional customer service, Islander Realty is the go-to agency for all your real estate needs in Captiva. Contact us today to start your property search or to list your home with us.

Matlacha Rental is a charming rental institution located at 12304 Boat Shell Drive in Matlacha Isles-Matlacha Shores, Florida, United States. Situated in the picturesque waterfront community of Matlacha, this rental offers visitors a cozy and comfortable accommodation option with stunning views of the surrounding area. Whether you are looking for a weekend getaway or an extended stay, Matlacha Rental provides a peaceful and relaxing atmosphere for guests to enjoy. With easy access to nearby beaches, restaurants, and outdoor activities, this institution is the perfect choice for those seeking a memorable vacation experience in Southwest Florida.

John R. Wood Properties - Pine Island Group is a reputable real estate agency located at 5400 Pine Island Road in Bokeelia, Florida. With a team of experienced and knowledgeable real estate agents, they specialize in helping clients buy and sell properties in the Pine Island area. Whether you are looking for a waterfront home, a vacation property, or a piece of land to build your dream home, the Pine Island Group can assist you every step of the way. Their dedication to providing top-notch service and expertise makes them a trusted choice for all your real estate needs in the beautiful surroundings of Pine Island, Florida.

Dream Vacation Rentals is a premier real estate and travel agency located at 2323 Wooster Lane in Sanibel, Florida. Specializing in vacation rentals on the stunning Sanibel Island and Captiva Island, our team is dedicated to helping you find the perfect accommodation for your dream getaway. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious condo, we have a wide selection of properties to choose from. With our personalized service and local expertise, we ensure that your vacation experience is seamless and unforgettable. Welcome to Dream Vacation Rentals, where your dream vacation becomes a reality.