TOP 30 Best Luxury beach property rentals in Sarasota, Florida

Peppertree Bay Vacation Rentals is a premier real estate and travel agency located at 6056 Midnight Pass Road in Sarasota, Florida. With a prime location just steps away from the beautiful beaches of the Gulf Coast, Peppertree Bay offers a wide selection of luxury vacation rentals perfect for a relaxing getaway. Whether you're looking for a cozy beachfront condo or a spacious waterfront villa, our experienced agents are dedicated to helping you find the perfect accommodation for your next vacation. Book with us today and experience the ultimate in comfort and convenience during your stay in Sarasota.

Welcome to Sunny Rentals, your premier destination for unforgettable vacation experiences in the heart of Sarasota, Florida. Conveniently located at 57 South Boulevard of the Presidents, our business is dedicated to providing you with top-quality rental services that cater to all your leisure needs. Nestled in the vibrant community of Sarasota, just steps away from pristine beaches and a lively cultural scene, Sunny Rentals offers a diverse selection of accommodations and recreational equipment to enhance your stay. Whether you're seeking a cozy beachside cottage, a luxurious waterfront condo, or the perfect gear for outdoor adventures, our friendly and knowledgeable team is here to ensure a seamless and enjoyable experience. Explore the beauty of Sarasota with Sunny Rentals and discover why we are the preferred choice for travelers seeking comfort, convenience, and exceptional service. Visit us today and let us help you create memories that will last a lifetime.

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.

Siesta Sands On the Beach is a premier lodging destination located at 118 Beach Road in Sarasota, Florida, United States. Our institution offers luxurious accommodations right on the beach, providing guests with stunning ocean views and easy access to the pristine white sand. As a real estate agency, we also specialize in beachfront properties for those looking to make their vacation dreams a reality. Additionally, our travel agency services can help guests plan the perfect getaway, whether it be a romantic retreat or a family vacation. Experience the ultimate beachfront escape at Siesta Sands On the Beach.

The Sarasota Surf & Racquet Club is a luxurious beachfront lodging institution located on the renowned Crescent Beach in Siesta Key, Florida. With spacious one and two-bedroom condominiums offering the comforts of home in a tropical paradise setting, this resort is perfect for couples or families. The property features two heated swimming pools, tennis and pickleball courts, a fitness center, and a recreation room for guests to enjoy. Just a short distance away is Siesta Key Village, where guests can explore restaurants, coffee shops, souvenir shops, nightclubs, and delicious ice cream. Voted the #1 Resort on Siesta Key by TripAdvisor, the Sarasota Surf & Racquet Club offers a world-class beach resort experience for visitors looking to relax and unwind on America's top beach.

Sunset Beach Resort is a charming lodging located at 76 Avenida Veneccia in the beautiful Siesta Key, Florida. This resort offers a tranquil and relaxing atmosphere with stunning views of the sunset over the Gulf of Mexico. The resort features cozy and comfortable accommodations, a sparkling swimming pool, and easy access to the beach. Guests can enjoy a peaceful getaway surrounded by the natural beauty of Siesta Key while being just a short drive away from the vibrant city of Sarasota. Experience the ultimate beach vacation at Sunset Beach Resort.

SUN N FUN PRIVATE VACATION RENTALS is a premier real estate and travel agency located at 7125 Fruitville Road in Sarasota, Florida. We specialize in providing luxurious and private vacation rentals for those looking to escape to the beautiful beaches and vibrant culture of Sarasota. Our team of experienced agents are dedicated to helping you find the perfect vacation rental for your needs, whether you are looking for a cozy beachfront condo or a spacious family home. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream getaway in sunny Sarasota.

iTrip Vacations Siesta Key (Sarasota-Venice) is a real estate and travel agency located at 5774 South Tamiami Trail in Sarasota, Florida, United States. Specializing in vacation rental management in Sarasota County, including Siesta Key, Lido Key, Casey Key, Nokomis, Osprey, and Venice, iTrip offers homeowners the opportunity to maximize their revenue with competitive rental rates, high bookings, and satisfied guests. With low fees, free maintenance, exposure on over 85 international websites, and no repair markup or rotation penalties, iTrip ensures that properties listed with them reach millions of potential renters through extensive advertising, marketing, and social media efforts. Contact iTrip Beaches of Sarasota today to increase your vacation rental income while reducing your workload.

Siesta Key Luxury Rental Properties is a prestigious real estate and travel agency located at 5231 Avenida Navarra in Sarasota, Florida. Specializing in luxury vacation rentals on Siesta Key, our agency offers a wide selection of exclusive properties for those seeking a truly unforgettable vacation experience. Whether you are looking for a beachfront villa, a waterfront estate, or a cozy cottage, our team of experienced agents are dedicated to helping you find the perfect rental property to suit your needs. With unparalleled customer service and attention to detail, Siesta Key Luxury Rental Properties is your go-to destination for luxury accommodations in the beautiful Sarasota area.

Siesta Key Beachfront Vacation Rentals is a premier real estate and travel agency located at 6312 Midnight Pass Road in Sarasota, Florida. Our agency specializes in offering luxurious vacation rentals right on the stunning beaches of Siesta Key. Whether you're looking for a cozy beachfront condo or a spacious waterfront villa, we have a wide selection of properties to choose from. Our dedicated team is committed to providing top-notch customer service and helping you find the perfect vacation rental for your stay in sunny Florida. Book with us today and experience the ultimate beachfront getaway!

Calini Beach Club is a premier destination located at 1030 Seaside Drive in Sarasota, Florida. As a luxurious lodging option, real estate agency, and travel agency all in one, Calini Beach Club offers guests the perfect blend of relaxation and convenience. With stunning ocean views, top-notch accommodations, and exceptional customer service, this institution is the ideal choice for those looking to experience the beauty of Sarasota. Whether you're in need of a vacation rental, looking to buy property in the area, or seeking assistance with booking your next trip, Calini Beach Club has everything you need to make your stay unforgettable.

Siesta Sun Beach Villas is a luxurious beachfront lodging option located at 6424 Midnight Pass Road in Sarasota, Florida. As a real estate and travel agency, we offer a range of stunning villas with breathtaking ocean views, perfect for a relaxing getaway or a romantic retreat. Our expert staff is dedicated to providing top-notch customer service and ensuring that each guest has a memorable and enjoyable experience. Whether you're looking for a weekend escape or a longer vacation, Siesta Sun Beach Villas is the perfect destination for your next trip to paradise.

Our House at the Beach by Tropical Sands Accommodations is a premier real estate and travel agency located at 1055 Beach Road in Sarasota, Florida. Nestled along the beautiful coastline of the Gulf of Mexico, our institution offers a wide range of beachfront properties for vacation rentals and real estate investments. With a dedicated team of professionals, we strive to provide exceptional customer service and personalized experiences for our clients. Whether you are looking for a luxurious beachfront condo for a relaxing getaway or a prime investment opportunity, Our House at the Beach is your go-to destination. Experience the beauty and tranquility of Sarasota's pristine beaches with us today.

Sandbox On the Beach is a charming lodging institution located at 108 Beach Road in Sarasota, Florida. Situated right on the beach, guests can enjoy stunning ocean views and easy access to the sandy shores. The property offers cozy accommodations with a beachy vibe, perfect for a relaxing getaway. With a laid-back atmosphere and a prime location, Sandbox On the Beach is the ideal destination for those looking to unwind and soak up the sun in beautiful Sarasota.

Parrot Beach Cottages is a charming and cozy 4-suite beach vacation rental property located on Siesta Key in Sarasota, Florida. Just steps away from the #1 rated beach in the United States, guests can enjoy spectacular sunsets, romantic walks on the beach, and relaxing by the swimming pool. The property is also within walking distance of Siesta Key Village, where guests can enjoy shopping, restaurants, live music, and more. For those looking for adventure, there are plenty of water activities available, such as kayaking, paddle boarding, parasailing, and fishing on the beautiful Gulf of Mexico. Additionally, guests can explore other local attractions, including the Ringling Museum, Marie Selby Botanical Gardens, Mote Marine, Jungle Gardens, St. Armands Circle for outdoor shopping and dining, and much more.

Gulf Coast Vacation Rentals is a premier real estate and travel agency located at 243 North Lime Avenue in Sarasota, Florida. We specialize in providing luxurious vacation rental properties along the stunning Gulf Coast of Florida. Our expert team is dedicated to helping you find the perfect rental for your next getaway, whether you're looking for a beachfront condo, a private villa, or a cozy cottage. With a wide range of properties to choose from and exceptional customer service, Gulf Coast Vacation Rentals is your go-to destination for an unforgettable vacation experience in the Sunshine State. Visit us today and start planning your dream vacation!

Ten35 Seaside Rentals is a premier lodging institution located at 1035 Seaside Drive in the beautiful city of Sarasota, Florida. Offering luxurious and comfortable accommodations, Ten35 is the perfect destination for those looking to relax and unwind by the seaside. With stunning views of the ocean and top-notch amenities, guests can enjoy a truly unforgettable stay. Whether you're planning a romantic getaway or a family vacation, Ten35 Seaside Rentals has everything you need for a memorable experience. Book your stay today and experience the ultimate in seaside luxury.

Gulf Gate Paradise - Vacation Rentals is a premier lodging option in Sarasota, Florida, offering a range of beautifully appointed vacation rentals for visitors to the Gulf Coast. Located at 5727 Olive Avenue, this institution is not only a lodging provider but also a real estate and travel agency, making it a one-stop shop for all your vacation needs. With a focus on providing top-notch customer service and luxurious accommodations, Gulf Gate Paradise is the perfect choice for those looking to experience the beauty and relaxation of the Florida coast. Book your stay today and experience paradise at Gulf Gate Paradise - Vacation Rentals.

Sienna Jewel Rentals is a premier real estate and travel agency located at 3441 Clark Road in Sarasota, Florida. Our agency specializes in providing luxurious vacation rentals and long-term property leases in the beautiful Sarasota area. Whether you are looking for a beachfront villa, a cozy condo, or a spacious family home, our experienced team is dedicated to helping you find the perfect property to suit your needs. With a wide variety of options to choose from, Sienna Jewel Rentals is your go-to destination for a memorable and comfortable stay in Sarasota. Contact us today to start planning your dream vacation or to secure your ideal rental property.

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.

Veloz Properties, located at 1375 Jackson Street in Fort Myers, Florida, is a premier institution offering annual rentals, vacation rentals, and homes for sale. With over 25 years of experience, we pride ourselves on providing the highest quality, most comfortable, and affordable living experience for our guests and tenants. Our property management services cover Lee, Charlotte, Hendry, and Sarasota counties in Southwest Florida. Whether you are looking for a vacation rental or interested in purchasing a property, Veloz Properties is here to help you make the right decision for your needs. Our team of experts specializes in construction, remodeling, and property investing, ensuring that we exceed your expectations with care, compassion, and professionalism.

Siesta Vacation Rentals is a premier real estate and travel agency located in Sarasota, Florida. Our expert team specializes in providing luxurious vacation rentals in the beautiful Sarasota area. Whether you are looking for a beachfront villa, a cozy cottage, or a spacious condo, we have the perfect accommodation for your next getaway. Our dedicated staff is committed to ensuring that your vacation is stress-free and unforgettable. Contact us today to book your dream vacation rental at Siesta Vacation Rentals.

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.

Crescent Beach 4 Rent is a reputable real estate and travel agency located at 6512 Midnight Pass Road in Sarasota, Florida. We specialize in providing luxurious beachfront rental properties for vacationers looking to experience the beauty of the Gulf Coast. Our team of experienced agents are dedicated to helping clients find the perfect rental property to suit their needs and create unforgettable memories. Whether you're looking for a cozy beach cottage or a spacious waterfront villa, Crescent Beach 4 Rent has a wide selection of properties to choose from. Contact us today to start planning your dream beach getaway in Sarasota!

Siesta Key Beach or Bay Rental is a reputable real estate and travel agency located at 6300 Midnight Pass Road in Sarasota, Florida. We specialize in providing luxurious beachfront and bayfront rentals for vacationers looking to experience the beauty and relaxation of Siesta Key. Our properties are meticulously maintained and offer top-notch amenities to ensure a comfortable and unforgettable stay. Whether you're seeking a romantic getaway, a family vacation, or a group retreat, our dedicated team is here to help you find the perfect rental that suits your needs. Contact us today to book your dream vacation on Siesta Key Beach or Bay!

Gertrude's Vacation Rentals at Crescent Beach, located on Point of Rocks Road in Sarasota, Florida, offers over 60 units in the best locations suitable for every group and budget. Whether you are a native, transplant, visitor, or local, the staff at Gertrude's understands that your vacation time is precious and is dedicated to providing the best experience possible. Situated near North America's best white sand beaches, guests can enjoy walking distance to world-famous shopping, dining, and entertainment options. The units feature private pools, ocean views, lagoon front decks, lazy hammocks, tiki huts, and rooftop sun decks. With personalized assistance from the staff, finding the perfect fit for you and your group is easy. Testimonials praise the cleanliness, beauty, and convenience of Gertrude's Vacation Rentals, making it the best Siesta Key experience. Whether it's your first time or a repeat visit, Gertrude's promises a seamless and enjoyable stay for all guests.

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.

Sandcastle Resort at Lido Beach is a charming lodging destination located right on the beautiful shores of Lido Beach in Sarasota, Florida. With its prime location at 1540 Benjamin Franklin Drive, guests can enjoy stunning views of the Gulf of Mexico and easy access to the soft sandy beach just steps away. The resort offers comfortable accommodations, a range of amenities including a pool, on-site dining options, and friendly service. Whether you're looking for a relaxing beach getaway or a fun-filled vacation, Sandcastle Resort at Lido Beach is the perfect choice for your stay in sunny Sarasota.

Siesta Beach House is a charming real estate and travel agency located at 5950 Midnight Pass Road in Sarasota, Florida. Our agency specializes in providing luxurious beachfront properties for rent and sale in the beautiful Siesta Key area. With stunning views of the Gulf of Mexico and direct access to the world-famous Siesta Key Beach, our properties offer the perfect vacation getaway or permanent residence. Our team of experienced agents is dedicated to helping clients find their dream beach house, whether for a relaxing vacation or a new place to call home. Contact us today to start your beachfront living experience at Siesta Beach House.