Luxury siesta key 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 Inn on Siesta Key is a charming lodging located at 515 Beach Road in Sarasota, Florida. Situated just steps away from the pristine white sands of Siesta Key Beach, this cozy inn offers guests a relaxing and luxurious retreat. With beautifully appointed rooms and suites, a sparkling pool, and friendly staff, The Inn on Siesta Key is the perfect destination for a romantic getaway or a family vacation. Enjoy the convenience of being close to shopping, dining, and outdoor activities while experiencing the tranquility of this beachfront oasis. Book your stay at The Inn on Siesta Key for a truly unforgettable experience.

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.

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.

Siesta Key Palms Resort is a charming lodging option located at 1800 Stickney Point Road in Sarasota, Florida. This resort offers a relaxing and comfortable stay for guests looking to experience the beauty of Siesta Key. With well-appointed rooms, a sparkling swimming pool, and easy access to the area's stunning beaches, Siesta Key Palms Resort is the perfect choice for a memorable vacation in the Sunshine State. Enjoy the warm hospitality and convenient amenities at this welcoming resort.

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.

Siesta Key Babuzziz is a charming lodging institution located at 1011 Crescent Street in Sarasota, Florida, United States. Nestled in the heart of Siesta Key, this cozy retreat offers a peaceful and relaxing atmosphere for guests to unwind and enjoy the beautiful surroundings. With comfortable accommodations and personalized service, Siesta Key Babuzziz is the perfect destination for a rejuvenating getaway. Whether you're looking to explore the nearby beaches, shops, and restaurants or simply relax by the pool, this hidden gem is sure to make your stay unforgettable.

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.

The Capri at Siesta is a charming lodging institution located at 6782 Sarasea Circle in Sarasota, Florida, United States. Situated in the beautiful and elegant surroundings of Sarasota and Siesta Key, The Capri offers comfortable rooms with kitchenettes, premium beds, and large flat screen TVs at competitive rates. Our goal is to provide guests with the best beach vacation experience on Siesta Key. We have recently renovated our hotel to create stylish and well-appointed guest rooms, a private garden courtyard for outdoor dining, and a heated pool for relaxation. Just a few steps away from our property is a private path lined with tropical flora that leads to the world-renowned Siesta Key Beach, known for its powdery white sand, gentle surf, and stunning sunsets.

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.

Welcome to Siesta Palms by the Beach, a premier lodging option located at 1017 Point of Rocks Road in Siesta Key, Florida. Formerly known as ‘Siesta Key Inn’ and ‘Siesta Palms’, our establishment offers a wide selection of large, family-friendly condos just a quick 1,300 feet from the beach. With pleasing amenities, a great location, and a friendly atmosphere, we are the perfect choice for your Siesta Key Crescent Beach vacation rental needs. Our amenities include an outdoor pool, garden, balcony and hot tub rooms, free wifi, and more. Each condo features a full kitchen with dishwasher, outdoor space, modern flat-screen television, and other unexpected features to make your stay comfortable and enjoyable. Turtle Beach is less than a mile away, and other area attractions such as Sarasota Beach, Point of Rocks Road, and Phillippi Estate Park are easily accessible from our location.

Twin Palms at Siesta is a stylishly redecorated lodging institution located at 1115 Point of Rocks Road in Sarasota, Florida. Offering well-appointed guest rooms, a private garden courtyard, and a newly remodeled pool, this charming retreat is just steps away from the world-renowned Siesta Key Beach. Known for its powdery white sand, warm gentle surf, and stunning sunsets, this beach is among the most beautiful in the world. The cozy and elegant rooms at Twin Palms feature kitchenettes, premium beds, and large flat-screen TVs, all at competitive rates. Guests rave about the friendly staff, cleanliness, and perfect location of this intimate beachside getaway. Enjoy relaxation in the natural beauty of Siesta Key at Twin Palms.

The Siesta Key Dream Inn is a luxurious lodging institution located at 5223 Calle Menorca in Sarasota, Florida, United States. Guests rave about the amazing location, just a short walk from the beach, restaurants, and bars. The units are impeccably clean and updated, with a beautiful beach vibe throughout. The service is top-notch, with friendly and helpful staff like Angela and Pete. The private balcony overlooks a stunning pool, and the landscaping is exquisite. Guests appreciate the comfortable bedding, great bathroom with double shower, and overall stunning interior design. Whether you're looking for a weekend getaway or an extended stay, the Siesta Key Dream Inn is the perfect choice for a memorable experience.

Siesta Sun Villas is a charming lodging institution located at 1016 Crescent Street in Sarasota, Florida, United States. Nestled in a peaceful and picturesque neighborhood, our villas offer a perfect blend of comfort and convenience. Each villa is tastefully decorated and fully equipped with modern amenities to ensure a relaxing stay for our guests. Just a short drive away from the famous Siesta Key Beach, our location is ideal for those looking to enjoy the sun, sand, and sea. Whether you are on a family vacation, a romantic getaway, or a business trip, Siesta Sun Villas is the perfect choice for your accommodation needs. Book your stay with us and experience the beauty of Sarasota in style and comfort.

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.

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.

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.

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.

Crescent Siesta Key Condominium Association is a premier lodging establishment located at 6512 Midnight Pass Road in Sarasota, Florida. As a real estate agency and travel agency, we offer luxurious vacation rentals and property management services for guests looking to experience the beauty of Siesta Key. Our condominiums are beautifully appointed and provide stunning views of the Gulf of Mexico. Whether you are looking for a relaxing beach getaway or a place to call home, Crescent Siesta Key Condominium Association has everything you need for a memorable stay in paradise.

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!

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.

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.

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.

Beachfront Siesta Key is a premier real estate and travel agency located at 8900 Blind Pass Road in Sarasota, Florida. Specializing in luxury beachfront properties and vacation rentals in the beautiful Siesta Key area, our experienced team is dedicated to helping clients find their dream seaside retreat. From stunning oceanfront condos to private beach villas, we offer a wide range of options to suit every taste and budget. Whether you are looking to buy, sell, or rent a beachfront property, Beachfront Siesta Key is your go-to destination for all things coastal living. Contact us today to start your journey to paradise!

The Anchorage on Siesta Key is a luxurious vacation rental institution located at 6415 Midnight Pass Road in Sarasota, Florida, United States. The management is known for their excellent communication and ensuring a smooth stay for all guests. Visitors rave about the extraordinary rental homes and the pleasant and friendly staff. The institution offers a top-notch vacation experience, with guests returning year after year. The Anchorage is the perfect place to book your holiday with Global Vacation Rentals, especially for events like the Fourth of July in Siesta Key or the Sarasota Powerboat Grand Prix Festival. Don't miss out on the opportunity to stay at this amazing institution!

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.

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.

Bianco Sands Siesta Key is a real estate and travel agency located at 1118 Point of Rocks Road in Sarasota, Florida, United States. The institution has a policy where 100% of total revenue will be forfeited if a reservation is canceled within 14 days, but reservations can be canceled outside of 14 days with a $50 restocking fee. In case of emergencies, such as hurricane evacuations, guests are advised to purchase trip insurance. Payment for reservations can be made with Visa, Mastercard, American Express, and Discover Card, with the first night's stay plus tax charged immediately upon booking. Guests have praised the institution for its nice location with easy beach access, clean apartments, and friendly staff. The property offers all comforts and provides quick responses to any inconveniences that may arise. Overall, Bianco Sands Siesta Key offers a pleasant stay with convenient amenities and a helpful staff.