TOP 30 Florida keys luxury rentals in Sarasota, Florida

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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.

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.

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.

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 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!

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!

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.

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.

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.

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.

SpeedBoat Tours Sarasota is a travel agency located at 946 Siesta Drive in Sarasota, Florida, United States. Your speed boat adventure awaits with a variety of exciting tours to choose from. Spend the day making memories on a fun boat ride to the best sandbars in Sarasota Bay, where you can relax in the warm, shallow water with a drink in hand. Perfect for bachelorette and bachelor parties, birthday celebrations, or simply escaping the beach crowds. Escape the beach crowds and witness breathtaking sunsets on a SpeedBoat Tour. Enjoy the wind in your hair as you cruise along Sarasota Bay, passing multi-million dollar mansions and possibly spotting dolphins along the way. Gift cards are available for purchase, making the perfect gift for any occasion.

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!

Siesta Key East is a premier real estate agency located at 1860 Baywood Drive in Sarasota, Florida. Specializing in luxury vacation rentals and property sales, Siesta Key East offers unparalleled service and expertise in the Sarasota area. As a top tourist attraction and travel agency, they provide visitors with the opportunity to experience the beauty and charm of Siesta Key while finding their dream vacation home or investment property. Whether you are looking for a beachfront condo or a waterfront estate, Siesta Key East has the perfect property for you. Contact them today to start your journey to paradise.

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.

Welcome to Coit Group Fine Homes, a premier real estate agency located in the heart of Tarpon Springs, Florida. Situated at 229 East Lemon Street, our agency proudly serves the vibrant communities of Trinity, Tarpon Springs, Land O Lakes, and Odessa. As a native of Clearwater, Florida, I bring a deep understanding and intricate knowledge of the Tampa Bay area to each client interaction, ensuring you receive the highest level of personalized service for all your real estate needs. Our agency specializes in a wide array of real estate services, including residential buying and selling, commercial and investment opportunities, luxury and vacation homes, and second homes. Whether you're in search of a single-family home, an office building, vacant land, or a condominium, we have the expertise to guide you through every step of the process. Our concierge service and commitment to client confidentiality are just the beginning of the exceptional service we provide.

Chart House, located at 201 Gulf of Mexico Drive in Longboat Key, Florida, is a top waterfront restaurant offering stunning views of Sarasota Bay. With a relaxing atmosphere both inside the dining room and outside on the terrace, this seafood restaurant is the perfect escape from the daily grind. Enjoy Happy Hour specials daily from 4PM to 6:30PM, as well as early dining hours from 4PM to 6PM. Indulge in delicious seafood specialties with a local twist, or sip on cocktails at the comfortable bar seating. Situated on beautiful Longboat Key, Chart House is a tropical retreat just a short drive away from outdoor destinations like South Lido County Park and Bay Island Park. With boat rentals, bike tracks, and more nearby, this restaurant is the ideal spot for a relaxing getaway. As they reopen their dining rooms, Chart House is committed to ensuring the safety of their guests and looks forward to serving you once again.

Your Personal Resort in Sarasota, Florida is the ultimate vacation rental property where you can escape from the daily grind and relax in luxury. Located at 3423 La Paloma Avenue, our three-story holiday residence and boating home offers premier access to the stunning beaches of Siesta Key, including Siesta Beach, Crescent Beach, Turtle Beach, Point of Rocks Beach, and Shell Beach for breathtaking sunsets. Our resort features a fitness center, bicycles, boat dock, beach equipment, outdoor grilling, and a beautiful outdoor pool and spa for your enjoyment. As a family-owned small business, we take a hands-on approach to managing your guest experience to ensure a hassle-free stay.

The Beach Club, located at 5151 Ocean Boulevard in Sarasota, Florida, is a popular bar and night club on Siesta Key. Whether you're looking to relax on the beach, catch a game, enjoy live music, or hit the dance floor, The Beach Club has something for everyone. Operating since (insert date), this institution offers a consistently friendly and fun experience for locals and tourists alike. With the best happy hour on the key, top-notch music, and a lively atmosphere, a visit to The Beach Club is sure to be a memorable one.

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.

Turtle Crawl Inn Resort is a beachfront paradise located at 4235 Gulf of Mexico Drive, Longboat Key, Florida. Offering easy living on the Gulf Coast, this resort features vacation beach condos near Sarasota, Florida. With a variety of room styles including accommodations at The Towers, The Gardens, and The Villas, guests can enjoy plush island luxury and quiet pleasures that cater to all personalities. The resort has 20 units directly facing the beautiful Gulf of Mexico, all with one bedroom, one bathroom, and a studio apartment style living area with a balcony overlooking the beach. Most units include a sleeper sofa and can accommodate up to 6 people. Guests can enjoy the heated pool, barbecue area, putting green, shuffleboard area, and easy access to the beach. The resort offers clean and comfortable rental condominiums and villas with fully equipped kitchens. Visitors can partake in activities such as shelling, biking, fishing, watersports, and dining, or simply relax on the white sand beaches and enjoy the warm Sarasota sun. With excellent views of the water and spectacular sunsets, Turtle Crawl Inn Resort is the perfect choice for a Longboat Key vacation. Previous guests have praised the resort for its friendly staff, peaceful atmosphere, and private beach access, making it a top choice for a relaxing getaway.

The Lido Islander is a premier institution located at 528 South Polk Drive in Sarasota, Florida. As a multi-faceted establishment, it serves as a lodging facility, real estate agency, and travel agency all in one. Whether you are looking for a luxurious place to stay, seeking to invest in property on Lido Key, or planning your next vacation, the Lido Islander offers a one-stop solution for all your needs. With a prime location in the beautiful city of Sarasota, the Lido Islander provides top-notch services and accommodations to ensure a memorable experience for all guests and clients.