TOP 10 Best Luxury vacation rentals with pool in Longboat Key, Florida

RVA Resort Vacations is a premier lodging, real estate, and travel agency located at 4030 Gulf of Mexico Drive in beautiful Longboat Key, Florida. With a focus on luxury accommodations and top-notch customer service, RVA Resort Vacations offers an array of vacation rental options, real estate opportunities, and travel services to suit every need. Whether you're looking for a relaxing beachfront retreat or a prime investment property, RVA Resort Vacations has you covered. Book your next vacation or find your dream home with RVA Resort Vacations today!

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.

INFINITY Longboat Key is a luxurious waterfront institution located at 4765 Gulf of Mexico Drive in Longboat Key, Florida, United States. This prestigious destination offers unparalleled views of the Gulf of Mexico and a serene beachfront setting. With world-class amenities and exceptional service, INFINITY Longboat Key is the ideal retreat for those seeking a sophisticated and relaxing escape. Whether you are looking to unwind by the pool, indulge in gourmet dining, or explore the natural beauty of the surrounding area, this exclusive institution promises a truly unforgettable experience.

Florida Vacation Connection is a premier lodging, real estate, and travel agency located at 3720 Gulf of Mexico Drive in Longboat Key, Florida. We specialize in providing top-notch vacation rentals, real estate services, and travel accommodations for those looking to experience the beauty and excitement of Florida. Our team of experienced professionals is dedicated to helping clients find the perfect vacation rental, buy or sell property, and plan unforgettable travel experiences in this stunning destination. Whether you're looking for a beachfront condo, a luxury estate, or a customized vacation package, Florida Vacation Connection has everything you need to make your Florida getaway truly unforgettable.

Vacation Villas at Longboat Key Club offers luxurious and spacious accommodations on the stunning Longboat Key in Florida. Situated at 220 Sands Point Road, this lodging institution provides guests with a perfect blend of relaxation and upscale amenities. With breathtaking views of the Gulf of Mexico and top-notch service, guests can enjoy a truly unforgettable vacation experience. Whether you're looking to unwind by the pool, play a round of golf, or explore the nearby attractions, Vacation Villas at Longboat Key Club is the perfect destination for a memorable getaway.

3 Palms by the Beach is a premier beachfront rental agency located on the stunning Longboat Key in Florida. Situated at 4325 Gulf of Mexico Drive, this institution offers luxurious vacation rentals with breathtaking views of the Gulf of Mexico. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, 3 Palms by the Beach has the perfect accommodations for you. With top-notch amenities and exceptional customer service, this real estate and travel agency is dedicated to helping you create unforgettable memories by the beach. Experience the beauty and tranquility of Longboat Key with 3 Palms by the Beach.

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.

Welcome to White Sands of Longboat, your perfect tropical getaway nestled in the heart of Longboat Key, Florida. Located at 5114 Gulf of Mexico Drive, our charming lodging offers a serene escape just steps away from the pristine beaches and turquoise waters of the Gulf of Mexico. At White Sands of Longboat, we pride ourselves on providing a tranquil and comfortable stay for every guest. Our well-appointed accommodations range from cozy rooms to spacious suites, each designed to offer a relaxing retreat with all the modern amenities you need. Enjoy the warm Florida sun as you lounge by our sparkling pool, or take a leisurely stroll along the powdery white sands just moments from your door.

Outrigger Resort by RVA is a charming lodging establishment located at 5155 Gulf of Mexico Drive in Longboat Key, Florida, United States. This resort offers a peaceful and relaxing atmosphere, perfect for a getaway by the beach. Guests can enjoy spacious accommodations, beautiful ocean views, and a range of amenities including a pool, tennis courts, and easy access to the beach. With friendly staff and a convenient location, Outrigger Resort by RVA is the ideal destination for a memorable vacation in Florida.

Cabana Beach Club is a luxurious lodging institution located on the pristine shores of Longboat Key, Florida. Situated at 5851 Gulf of Mexico Drive, this exclusive beach club offers guests a tranquil and upscale retreat with breathtaking views of the Gulf of Mexico. The Cabana Beach Club features well-appointed accommodations, including spacious rooms and suites, as well as a range of amenities such as a private beach, swimming pool, and on-site dining options. Whether you're looking for a romantic getaway or a relaxing family vacation, Cabana Beach Club provides the perfect setting for a memorable stay in paradise.

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 Diplomat Beach Resort is a luxurious lodging destination located at 3155 Gulf of Mexico Drive in Longboat Key, Florida, United States. This prestigious resort offers unparalleled comfort and service, making it the perfect retreat for those seeking a relaxing getaway. With stunning views of the Gulf of Mexico and a range of amenities including a pool, spa, and fine dining options, guests are sure to have a memorable stay. Whether you're looking for a weekend escape or a long-term rental, The Diplomat Beach Resort is the ideal choice for your next vacation or real estate investment.

Four Winds Beach Resort is a charming lodging establishment located on the stunning Gulf of Mexico Drive in Longboat Key, Florida. This beachfront resort offers guests a serene and tranquil escape with breathtaking views of the ocean. The resort features comfortable accommodations, a sparkling outdoor pool, direct beach access, and a variety of amenities to ensure a relaxing stay. Whether you're looking to unwind by the water or explore the nearby attractions, Four Winds Beach Resort is the perfect destination for your next getaway.

Veranda Beach Club is a luxurious lodging destination located on the stunning Gulf of Mexico Drive in Longboat Key, Florida. This exclusive resort offers a range of beautiful accommodations, from cozy beachfront villas to spacious suites with breathtaking ocean views. Guests can relax by the pool, stroll along the white sandy beach, or enjoy a variety of water sports and activities. With its prime location and top-notch amenities, Veranda Beach Club is the perfect getaway for those seeking a tranquil and upscale vacation experience. Additionally, as a real estate agency, the institution also offers opportunities to own a piece of paradise in this desirable coastal community.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

LaPlaya Condominiums is a luxurious beachfront property located at 4425 Gulf of Mexico Drive in Longboat Key, Florida. This stunning complex offers a range of beautifully appointed condominiums for sale or rent, perfect for those seeking a tropical getaway or a permanent residence in paradise. With pristine white sand beaches just steps away and breathtaking views of the Gulf of Mexico, LaPlaya Condominiums is the perfect destination for those looking to relax and unwind in style. Whether you're looking for a vacation rental or a new home, LaPlaya Condominiums has something for everyone. Contact us today to learn more about this exclusive property and start living the beachfront lifestyle you've always dreamed of.

Sand Cay Beach Resort is a luxurious beachfront property located at 4725 Gulf of Mexico Drive in Longboat Key, Florida. This stunning resort offers a range of real estate options, from beautiful beachfront condos to cozy cottages. Whether you're looking for a vacation rental or a permanent home, Sand Cay Beach Resort has something for everyone. With its prime location on the Gulf of Mexico, guests can enjoy breathtaking views, white sandy beaches, and a host of amenities such as a pool, tennis courts, and direct beach access. The resort also offers concierge services to help guests make the most of their stay in this idyllic seaside paradise. Experience the ultimate in beachfront living at Sand Cay Beach Resort.