TOP 30 Best Luxury vacation rentals in Sarasota, Florida

Sea Crest On Siesta Key is a luxurious lodging institution located at 1129 Seaside Drive in Sarasota, Florida, United States. Situated just steps away from the pristine white sands of Siesta Key Beach, this institution offers comfortable accommodations with stunning ocean views. Guests can relax by the pool, enjoy beach access, and explore the nearby shops and restaurants. With its prime location and upscale amenities, Sea Crest On Siesta Key is the perfect destination for a beach getaway in Florida.

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.

Siesta Sands Beach Resort is a charming lodging located at 1001 Point of Rocks Road in Sarasota, Florida. Situated right on the beautiful shores of the Gulf of Mexico, this resort offers guests a relaxing and luxurious beachfront experience. With spacious and well-appointed accommodations, guests can enjoy stunning ocean views, direct beach access, and a range of amenities including a pool, hot tub, and BBQ area. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Siesta Sands Beach Resort provides the perfect setting for a memorable stay in sunny Florida.

Siesta Key Bungalows is a charming lodging establishment located at 8212 Midnight Pass Road in Sarasota, Florida. Nestled in the heart of Siesta Key, just steps away from the pristine white sands of the beach, our bungalows offer a cozy and comfortable retreat for guests looking to relax and unwind. Each bungalow is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Whether you're looking for a romantic getaway or a fun family vacation, Siesta Key Bungalows is the perfect choice for your next trip to the Sunshine State.

Palm Aire Country Club is a premier golf and country club located at 5601 Country Club Way in Sarasota, Florida. With a rich history dating back to 1957, Palm Aire offers members and guests a luxurious and welcoming atmosphere to enjoy a round of golf, tennis, swimming, dining, and social events. The club features two championship golf courses designed by renowned architects, a state-of-the-art tennis facility, a sparkling swimming pool, and exquisite dining options. Whether you are a seasoned golfer or just looking for a relaxing day at the club, Palm Aire Country Club provides the perfect setting for recreation and socializing in beautiful Sarasota.

Sea Club II Condominiums is a luxurious beachfront property located at 5955 Midnight Pass Road in Sarasota, Florida. Offering stunning views of the Gulf of Mexico, this institution provides guests with a relaxing and upscale vacation experience. The condominiums are beautifully appointed with modern amenities and spacious living areas, perfect for families or couples looking for a beach getaway. Guests can enjoy the pristine white sand beach, sparkling pool, and lush tropical landscaping that surrounds the property. With easy access to shopping, dining, and outdoor activities, Sea Club II Condominiums is the perfect destination for a memorable vacation in sunny Sarasota.

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.

Fisherman's Cove is a premier real estate agency located at 9000 Blind Pass Road in Sarasota, Florida. With a prime location in the heart of the vibrant Sarasota community, Fisherman's Cove specializes in helping clients find their dream waterfront properties. Whether you're looking for a beachfront condo, a luxury estate on the bay, or a charming coastal cottage, our team of experienced agents is dedicated to providing personalized service and expert guidance throughout the buying or selling process. Trust Fisherman's Cove to help you navigate the competitive Sarasota real estate market and find the perfect property to suit your lifestyle and budget.

Stoneybrook Golf and Country Club is a premier golf and country club located at 8801 Stoneybrook Boulevard in Sarasota, Florida, United States. With its meticulously maintained 18-hole championship golf course, stunning clubhouse, and array of luxury amenities, Stoneybrook offers a first-class experience for members and guests alike. Whether you're looking to improve your golf game, relax by the pool, or indulge in fine dining, Stoneybrook Golf and Country Club has something for everyone. Come and experience the ultimate in country club living at Stoneybrook.

Welcome to The O'Steen Group, Inc. - Your Trusted Property Partner Located at 6680 Cortez Road West, Bradenton, Florida, The O'Steen Group, Inc. is a family-owned and operated real estate brokerage and property asset management company, proudly serving the community since 2007. We specialize in finance, real estate, and travel services, catering to the unique needs of our clients with a personal touch.

Ameniti Bay, BW Signature Collection is a luxurious lodging facility located at 5985 Brookhill Boulevard in Sarasota, Florida, United States. This exquisite establishment offers top-tier amenities and exceptional service to ensure a memorable stay for guests. With beautifully appointed rooms, stunning views, and convenient access to nearby attractions, Ameniti Bay is the perfect choice for travelers seeking a sophisticated and comfortable accommodation experience. Whether you are visiting for business or pleasure, Ameniti Bay, BW Signature Collection promises a truly unforgettable stay.

Hibiscus Suites is a charming lodging institution located at 1735 Stickney Point Road in Sarasota, Florida, United States. Nestled in a beautiful tropical setting, Hibiscus Suites offers comfortable and spacious suites for guests looking for a relaxing getaway. The property features a serene outdoor pool, lush gardens, and a convenient location near the beach and local attractions. Whether you are visiting Sarasota for business or pleasure, Hibiscus Suites provides a peaceful retreat for your stay. Experience the warm hospitality and inviting atmosphere of Hibiscus Suites during your next visit to Sarasota.

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.

Sea Club V Beach Resort is a charming lodging institution located at 6744 Sarasea Circle in Sarasota, Florida. Situated right on the beautiful shores of the Gulf of Mexico, this resort offers guests a relaxing and luxurious beachfront experience. With spacious rooms, stunning ocean views, and top-notch amenities, Sea Club V Beach Resort is the perfect destination for a beach getaway. Whether you're looking to soak up the sun on the sandy shores, take a dip in the crystal-clear waters, or simply unwind and enjoy the peaceful surroundings, this resort has everything you need for a memorable stay. Experience the ultimate beach vacation at Sea Club V Beach Resort.

Old Prairie Campground is a peaceful retreat nestled in the heart of Sarasota, Florida. This charming campground offers a serene atmosphere surrounded by lush greenery and towering trees. Visitors can choose from a variety of lodging options, including tent sites, RV hookups, and cozy cabins. The campground also features a range of amenities, including picnic areas, hiking trails, and a playground for children. Whether you're looking to relax in nature or explore the nearby attractions, Old Prairie Campground is the perfect destination for a memorable getaway.

Solaire Apartments is a premier real estate agency located at 5350 Desoto Road in Sarasota, Florida. Situated in the trendy Sarasota area, Solaire Apartments offers luxurious lifestyle-tailored living within walking distance to the popular restaurants, shops, and entertainment of University Town Center (UTC). The contemporary tropical architecture of Solaire spreads out over 10 acres of beautiful landscape, providing 1, 2, and 3 bedroom designer smoke-free rental residences. Residents can enjoy five-star luxury amenities and a fresh new take on city center living. Experience unmatched living at Solaire Apartments in Sarasota.

Midnight Cove is a premier real estate and travel agency located at 6302 Midnight Cove Road in the beautiful city of Sarasota, Florida. Our dedicated team of professionals are committed to helping clients find their dream vacation rental or purchase their perfect property in this stunning coastal destination. Whether you're looking for a luxurious beachfront condo or a charming vacation home, Midnight Cove has a wide selection of properties to choose from. With our expertise in the local real estate market and our personalized approach to customer service, we strive to make your experience with us seamless and enjoyable. Contact us today to start your journey towards finding the ideal property or vacation rental in Sarasota.

Sea Shell Condos is a premier lodging destination located at 6500 Midnight Pass Road in Sarasota, Florida. As a combination of a real estate agency and travel agency, Sea Shell Condos offers luxurious accommodations in a stunning beachfront setting. With a wide range of amenities and services, guests can enjoy a relaxing and unforgettable stay. Whether you are looking for a vacation rental or a permanent residence, Sea Shell Condos is the perfect place to experience the beauty and charm of Sarasota.

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.

Preferred SHORE Real Estate is a reputable real estate agency located at 50 South Lemon Avenue in Sarasota, Florida, United States. With a team of experienced and dedicated agents, we specialize in helping clients buy, sell, and rent properties in the Sarasota area. Our mission is to provide top-notch customer service and expert guidance throughout the real estate process. Whether you are looking for your dream home, an investment property, or a vacation rental, Preferred SHORE Real Estate is here to help you every step of the way. Contact us today to see how we can assist you with all of your real estate needs.

Shore is a trendy clothing store located at 465 John Ringling Boulevard in Sarasota, Florida. Offering a wide selection of fashionable apparel and accessories, Shore is a go-to destination for those looking to update their wardrobe with the latest styles. With its prime location in the heart of Sarasota, this store is a must-visit for fashion-forward individuals seeking quality pieces at affordable prices. Whether you're looking for casual everyday wear or something more formal for a special occasion, Shore has something for everyone. Come visit us today and experience the best in fashion at Shore.

Lido Beach Resort is a luxurious lodging institution located at 700 Benjamin Franklin Drive in Sarasota, Florida, United States. Situated right on the beautiful Lido Beach, this resort offers stunning ocean views, upscale accommodations, and top-notch amenities. Guests can relax by the pool, dine at the on-site restaurant, or take a short walk to the nearby shops and restaurants. With its prime location and exceptional service, Lido Beach Resort is the perfect destination for a relaxing beach getaway.

Tiny House Siesta is a unique lodging institution located in Sarasota, Florida, United States. Situated at 6600 Avenue A, this charming establishment offers a one-of-a-kind experience for guests looking to escape the hustle and bustle of everyday life. Each tiny house is expertly designed and decorated to provide a cozy and comfortable stay, with all the amenities needed for a relaxing getaway. Whether you're looking for a romantic retreat or a family vacation, Tiny House Siesta has something for everyone. Come and experience the beauty of Sarasota while staying in these adorable tiny homes.

Siesta Key Beachside Villas is a charming lodging option located at 124 Columbus Boulevard in the beautiful city of Sarasota, Florida, United States. Situated just steps away from the pristine white sands and crystal-clear waters of Siesta Key Beach, this beachside retreat offers guests a relaxing and luxurious stay. The villas are tastefully decorated and equipped with modern amenities, providing a comfortable and convenient home away from home. Whether you're looking to unwind by the pool, explore the vibrant local area, or simply soak up the sun on the beach, Siesta Key Beachside Villas is the perfect choice for your next vacation getaway.

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.

The Row Waterside Apartments is a luxurious residential complex located at 1420 Lakefront Drive in Sarasota, Florida. Situated right on the waterfront, residents can enjoy stunning views of the lake and surrounding natural beauty. The apartments offer spacious layouts, modern amenities, and high-end finishes, making it the perfect place to call home. With a prime location near shopping, dining, and entertainment options, The Row Waterside Apartments provides a convenient and upscale lifestyle for its residents. Experience waterfront living at its finest at this prestigious Sarasota address.

Crescent Royale Condominiums is a luxurious lodging option located at 777 Beach Road in the beautiful city of Sarasota, Florida. As a premier real estate agency, we offer stunning beachfront condos with breathtaking views of the Gulf of Mexico. Our spacious and well-appointed units are perfect for both short-term vacation rentals and long-term stays. Guests can enjoy a range of on-site amenities including a pool, fitness center, and direct beach access. Experience the ultimate in comfort and convenience at Crescent Royale Condominiums.

Jennette Properties is a premier real estate institution located in Sarasota, Florida, with additional offices in University Park/Lakewood Ranch and Bradenton. Specializing in leasing distinctive properties for extraordinary people, Jennette Properties offers a wide range of rental options for clients. With a dedicated team of professionals, Jennette Properties is committed to providing exceptional service and finding the perfect property for each individual. Contact us today to learn more about our available properties and start your leasing journey with Jennette Properties.

Overseas Realty is a premier real estate agency located at 786 South Orange Avenue in Sarasota, Florida. With over 40 years of experience, Overseas Realty is your trusted partner for luxury properties and investment opportunities in Florida, Costa Rica, and Ecuador. Our expert team offers strategic insights into vibrant real estate markets, prime rentals in Sarasota and Manatee County, and hassle-free property management services tailored to your needs. Whether you're looking to buy, sell, or manage a property, Overseas Realty is here to help. Our diverse real estate portfolio includes retirement hotspots, vacation homes, and investment properties to fit your unique lifestyle and goals. With enhanced features on our website, accessing essential services has never been easier.