TOP 30 Luxury vacation rentals in Sarasota, Florida

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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.

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.

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 Beach Rentals is a premier lodging establishment located at 5213 Calle Menorca in Sarasota, Florida. Offering a wide range of vacation rentals including beachfront condos and cozy cottages, Siesta Beach Rentals provides guests with a comfortable and luxurious home away from home. With top-notch amenities, stunning views of the beach, and exceptional customer service, Siesta Beach Rentals is the perfect choice for a relaxing getaway on the beautiful shores of Sarasota.

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.

Sarasota South is a reputable real estate agency located at 4515 26th Street West in Bradenton, Florida, United States. With a team of experienced and knowledgeable agents, Sarasota South is dedicated to helping clients buy, sell, and rent properties in the Sarasota area. Whether you are looking for a new home, investment property, or vacation rental, Sarasota South is committed to providing exceptional service and expertise to meet your real estate needs. Contact us today to start your real estate journey with Sarasota South.

Wendy Lynn Group - Fine Properties Sarasota is a prestigious real estate agency located at 5224 Paylor Lane in Sarasota, Florida. With a reputation for excellence and a dedication to providing the highest level of service, Wendy Lynn Group specializes in luxury properties in the Sarasota area. Whether you are buying or selling a home, their team of experienced agents will guide you through every step of the process with professionalism and expertise. Trust Wendy Lynn Group - Fine Properties Sarasota to help you find your dream home or sell your property for top dollar.

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!

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!

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.

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.

Sarasota Cottage Rentals/Treetop is a premier real estate and travel agency located in the beautiful city of Sarasota, Florida. Situated at 1776 Cherry Lane, this institution offers a wide range of luxurious cottage rentals and treetop accommodations for those looking to experience the ultimate vacation getaway. With stunning views and top-notch amenities, Sarasota Cottage Rentals/Treetop is the perfect choice for those seeking a relaxing and unforgettable stay in this picturesque destination. Whether you're looking for a cozy cottage or a treetop retreat, this agency has you covered with their exceptional service and attention to detail. Book your dream vacation with Sarasota Cottage Rentals/Treetop today and make memories that will last a lifetime.

Sarasota Cottage Rentals/Sapphire Cottage is a premier real estate and travel agency located in the vibrant city of Sarasota, Florida. Situated at 535 Ohio Place, our agency specializes in providing luxurious and well-appointed cottage rentals for those looking to experience the beauty and charm of Sarasota. Whether you are seeking a relaxing beach getaway or a fun-filled family vacation, our team of dedicated professionals is here to help you find the perfect rental property to suit your needs. From cozy beachfront cottages to spacious downtown retreats, Sarasota Cottage Rentals/Sapphire Cottage has something for everyone. Contact us today to start planning your dream vacation in sunny Sarasota!

Sarasota Cottage Rentals/Hudson Bayou is a premier real estate and travel agency located in Sarasota, Florida. Situated at 850 South Tamiami Trail, this institution offers a wide selection of luxurious cottage rentals in the picturesque Hudson Bayou area. Whether you are looking for a cozy retreat for a romantic getaway or a spacious home for a family vacation, Sarasota Cottage Rentals/Hudson Bayou has the perfect accommodation for you. With expert agents who are knowledgeable about the local area and dedicated to providing top-notch customer service, this agency is your go-to destination for a memorable and relaxing stay in Sarasota. Book your dream cottage rental today and experience the beauty and charm of Hudson Bayou with Sarasota Cottage Rentals/Hudson Bayou.

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.

Vunique Vacations is a premier real estate and travel agency located at 1144 Tallevast Road in Sarasota, Florida. We specialize in providing unique and unforgettable vacation experiences for our clients. Whether you're looking for a luxury beachfront property or a charming villa in the countryside, our team of experts is here to help you find the perfect vacation rental. With years of experience in the industry, we have established relationships with top properties around the world to ensure that you have access to the best accommodations. Contact us today to start planning your dream vacation with Vunique Vacations.

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.

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!

Roelens Vacation Rentals is a premier travel agency located at 677 North Washington Boulevard in Sarasota, Florida, United States. We specialize in providing high-quality vacation rental properties for visitors looking to experience the beauty and excitement of the Sarasota area. Our team is dedicated to helping our clients find the perfect accommodation for their stay, whether they are looking for a beachfront condo, a cozy cottage, or a luxury villa. With our attention to detail and commitment to customer satisfaction, Roelens Vacation Rentals ensures that every guest has a memorable and enjoyable vacation experience. Contact us today to start planning your dream getaway to Sarasota!

Rent Sarasota, LLC is a reputable rental agency located at 1000 North East Avenue in Sarasota, Florida. We specialize in providing high-quality rental properties for both short-term and long-term stays in the beautiful Sarasota area. Our team of experienced professionals is dedicated to helping clients find the perfect rental that suits their needs and preferences. Whether you are looking for a cozy apartment, a spacious house, or a luxurious vacation rental, Rent Sarasota, LLC has a wide range of options to choose from. Contact us today to find your dream rental in Sarasota!

Gulf Coast Rental Homes is a reputable real estate and travel agency located at 677 North Washington Boulevard in Sarasota, Florida, United States. Specializing in vacation rentals along the stunning Gulf Coast, this agency offers a wide selection of luxurious properties for short-term stays. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious condo, Gulf Coast Rental Homes has the perfect accommodation for your next getaway. With top-notch customer service and a range of amenities, this agency ensures a memorable and comfortable stay for all guests. Experience the beauty of the Gulf Coast with Gulf Coast Rental Homes.

Rez Rentals LLC is a premier real estate and travel agency located at 1960 Stickney Point Road in Sarasota, Florida. Specializing in vacation rentals and property management, we offer a wide range of accommodations to suit every traveler's needs. Our team of experienced agents is dedicated to providing exceptional customer service and helping clients find the perfect rental property for their stay in the beautiful Sarasota area. Whether you're looking for a beachfront condo, a cozy cottage, or a luxury villa, Rez Rentals LLC has you covered. Contact us today to start planning your dream vacation!

Seaside Resort Rentals is a premier real estate and travel agency located at 6202 South Tamiami Trail in Sarasota, Florida. We specialize in providing luxurious vacation rentals along the beautiful beaches of Sarasota and the surrounding areas. Our team of experienced agents are dedicated to helping you find the perfect rental property for your next beach getaway. Whether you are looking for a cozy beachfront cottage or a spacious oceanfront villa, we have a wide selection of properties to choose from. Contact us today to start planning your dream beach vacation with Seaside Resort Rentals.

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 [email protected]. Enjoy a luxurious and secluded getaway at Siesta Key Heritage House.

Gumbo Limbo Vacation Rentals is a premier real estate and travel agency located at 664 Calle Del Otono in Sarasota, Florida. We specialize in offering luxurious vacation rentals in the beautiful Sarasota area, providing our clients with the perfect home away from home during their stay. Our dedicated team of professionals is committed to ensuring that every guest has a memorable and enjoyable experience while visiting our stunning coastal city. Whether you are looking for a beachfront villa, a cozy cottage, or a spacious condo, Gumbo Limbo Vacation Rentals has the perfect accommodation to suit your needs. Contact us today to book your next unforgettable vacation in Sarasota!

Longboat Key Luxury is a prestigious real estate agency located on Gulf of Mexico Drive in Longboat Key, Florida. Recognized as the top sales team in the state of Florida with Coldwell Banker in 2022, we are in the top 0.5% for all Coldwell Banker Realtors® worldwide. Led by the Kepecz-Hays Team, we have sold over $173 million in the last two years and five months, with a career sales total of over $2.4 billion. Our extensive network of REALTORS® in European countries has helped us establish a strong presence in the luxury real estate market. Located at 2251 Gulf of Mexico Drive, #204, Longboat Key, FL 34228, our agency specializes in luxury properties in Longboat Key, Lido Key, and Sarasota. We offer premier properties and private viewings for buyers, along with expert marketing strategies to ensure a seamless buying or selling experience. With a focus on waterfront neighborhoods, we provide unparalleled excellence in Florida's elite real estate market.

Sea Club 8B Resort Rentals, LLC is a real estate and travel agency located at 5955 Midnight Pass Road in Sarasota, Florida, United States. If you're looking for a home-away-from-home for your vacation, look no further than our Siesta Key condo rentals. Situated on the Gulf of Mexico, Siesta Key offers warm crystal blue waters, tropical breezes, and stunning sunsets. Whether you're planning a family vacation, winter escape, or romantic getaway, Sea Club II has something for everyone. With a top-rated beach, nightlife, shopping, and dining options, Siesta Key is the ultimate Florida destination. The soft, white quartz sand at Siesta Beach is perfect for barefoot walks and sunbathing. Our guests love the cozy and clean accommodations, private beach access, and comfortable beds.

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!