The 30 Best Sailing vacation rentals in St. Petersburg, Florida

Captain Stefan Yacht Charters & ASA Sailing School is a premier institution located in the heart of St. Petersburg, Florida. As a top-rated sailing school and travel agency, we offer a range of courses and charters for all levels of experience. Whether you are a beginner looking to learn the ropes or an experienced sailor wanting to hone your skills, our expert instructors are here to help you achieve your sailing goals. Our location at 1110 3rd Street South provides easy access to the beautiful waters of the Gulf Coast, making it the perfect setting for an unforgettable sailing experience. Join us at Captain Stefan Yacht Charters & ASA Sailing School and set sail on your next adventure today!

The Doyle Sailing Center is a premier sailing institution located at 4200 54th Avenue South in St. Petersburg, Florida, United States. Offering a wide range of sailing programs for all ages and skill levels, the center is dedicated to providing top-notch instruction and resources for those looking to learn or improve their sailing abilities. With experienced instructors, state-of-the-art facilities, and a passion for the sport, the Doyle Sailing Center is the perfect place to embark on your sailing journey. Whether you're a beginner looking to try sailing for the first time or a seasoned sailor looking to hone your skills, the Doyle Sailing Center has something for everyone.

The St. Petersburg Sailing Center is a premier destination for sailing enthusiasts located at 250 2nd Avenue Southeast in St. Petersburg, Florida, United States. Offering a range of sailing programs, classes, and events for all skill levels, the center provides a unique opportunity to experience the thrill of sailing on the beautiful waters of Tampa Bay. With experienced instructors, top-of-the-line equipment, and a welcoming atmosphere, the St. Petersburg Sailing Center is the perfect place to learn, improve, and enjoy the sport of sailing. Whether you're a beginner looking to try something new or an experienced sailor seeking to hone your skills, the center has something for everyone. Join us at the St. Petersburg Sailing Center and discover the joy of sailing today!

Smooth Sailing with V is a travel agency located at 7901 4th Street North in St. Petersburg, Florida. Specializing in unforgettable sailing experiences, we offer a fun and satisfying time at sea, particularly during the captivating sunset hours. Our trips typically last 2-3 hours between 4pm and 8pm, with pricing varying depending on the package chosen. For those looking to celebrate a special occasion such as a birthday, anniversary, or honeymoon, we offer customizable sailing experiences with hours tailored to the customer's preferences. Prices start at $200-$1,000 hourly for boat rental with a Captain, with rates varying based on boat size, type, and party size.

Bird Dog Custom Boat Charters Clearwater & St Pete is a premier travel agency located at 2848 Saint John Drive in Clearwater, Florida. Since 1997, we have been providing unforgettable experiences for those seeking adventure, nature enthusiasts, and couples looking for a romantic getaway. Our dedication to exceptional service and passion for the sea sets us apart from the rest. When you choose Bird Dog Custom Boat Charters Clearwater & St. Pete, you are not just booking a boat trip; you are opening the door to a world of unparalleled experiences. With over 20 years of experience, we are your trusted guides to the stunning coastal areas of Clearwater and St. Petersburg. Our goal is to create custom adventures that cater to your preferences, ensuring that each journey is unique and unforgettable.

Tampa Bay Sunset Sail is a luxury travel agency located at 500 1st Avenue Southeast in St. Petersburg, Florida. Step aboard the Hawkeye, a new 47-foot luxury sailboat crafted by Island Packet Yachts, and embark on a two-hour sunset cruise along Downtown St. Petersburg's picturesque waterfront. Watch as the city skyline shimmers in the fading light of the sun. With a professional captain at the helm, guests can choose between a private or shared boating experience for up to six people. Perfect for romantic evenings, family outings, birthdays, vacations, staycations, and more, this sunset sail offers a unique and unforgettable way to experience Tampa Bay.

Cruisin' Tikis St. Pete is a unique travel agency located in St. Petersburg, Florida. Situated at 500 1st Avenue Southeast, this institution offers a one-of-a-kind experience for those looking to explore the beautiful waters of Florida in style. Guests can hop aboard a tiki boat and cruise along the coast, enjoying the scenic views and tropical vibes. Whether you're looking for a relaxing day on the water or a fun party with friends, Cruisin' Tikis St. Pete is the perfect choice for your next adventure. Book your excursion today and get ready to set sail on an unforgettable journey!

The St. Petersburg Yacht Club is a prestigious and exclusive institution located at 11 Central Avenue in St. Petersburg, Florida. Boasting a prime waterfront location, the club offers members access to a wide range of amenities and activities, including sailing, boating, social events, and fine dining. With a rich history dating back to its founding in 1909, the St. Petersburg Yacht Club is a hub for avid sailors and water enthusiasts in the area. Whether you're looking to relax by the water, participate in regattas, or simply enjoy the company of fellow members, the St. Petersburg Yacht Club provides a luxurious and welcoming environment for all.

Captain de Jong Charters is a renowned institution located at 400 2nd Avenue Northeast in St. Petersburg, Florida, United States. As a school and travel agency specializing in marine adventures, Captain de Jong Charters offers a wide range of courses and experiences for those looking to explore the open waters. Whether you're a seasoned sailor or a novice looking to learn the ropes, our experienced instructors are dedicated to providing top-notch education and unforgettable excursions. Join us at Captain de Jong Charters and set sail on the journey of a lifetime.

SailTime Tampa Bay is a premier sailing club located at 1421 Bay Street Southeast in St. Petersburg, Florida. As a member of SailTime, you have access to a fleet of top-of-the-line sailboats, including monohulls and catamarans, all available for your sailing adventures on the beautiful waters of Tampa Bay. Whether you are a seasoned sailor or a beginner looking to learn, SailTime offers a range of membership options and sailing courses to suit your needs. Join us and experience the joy of sailing in the stunning surroundings of St. Petersburg, Florida.

Salt and Mist Sea Tours is a premier travel agency located in St. Petersburg, Florida, specializing in unforgettable sea adventures. Our experienced team is dedicated to providing exceptional service and creating unforgettable memories for our clients. Whether you're looking for a relaxing sunset cruise, a thrilling deep-sea fishing excursion, or a romantic private yacht charter, we have the perfect experience for you. Join us at 6701 Sunshine Skyway Lane South and let us help you explore the beauty of the open sea.

Pirate City Boat Charters is a popular tourist attraction and travel agency located in St. Petersburg, Florida. Set sail on a memorable adventure aboard one of their luxurious boats and explore the beautiful waters of the Gulf Coast. Whether you're looking for a relaxing cruise, a thrilling fishing expedition, or a romantic sunset tour, Pirate City Boat Charters has something for everyone. Their experienced crew will ensure you have a safe and enjoyable experience as you soak in the stunning views and create lasting memories. Book your next nautical adventure with Pirate City Boat Charters and discover the magic of the sea.

Soulshine Charters is a premier travel agency located in St. Petersburg, Florida. Our dedicated team specializes in providing unforgettable charter experiences for those looking to explore the beautiful waters of the Gulf Coast. Whether you're seeking a relaxing day of fishing, a thrilling snorkeling adventure, or a romantic sunset cruise, Soulshine Charters has the perfect excursion for you. Join us at our convenient location on 14th Avenue North and let us help you create memories that will last a lifetime.

Welcome to Lakewood Travel Park! Nestled in the heart of Hudson, Florida, just off the Gulf Coast, Lakewood Travel Park is your perfect getaway destination. Located at 11517 State Road 52, our park offers a serene escape for RV enthusiasts, snowbirds, and vacationers alike. Whether you're looking for a short stay or a long-term retreat, our campground and lodging facilities provide a welcoming atmosphere with a variety of amenities to enhance your experience.

Welcome to Sand Dollar Charters St. Pete Beach, your premier travel agency located in the heart of St. Petersburg, Florida. Nestled at 737 Pinellas Bayway South, we specialize in crafting unforgettable maritime adventures that capture the essence of Florida's stunning coastline. Whether you're seeking a serene sunset cruise, an exhilarating deep-sea fishing expedition, or a bespoke island-hopping experience, our expert team is dedicated to tailoring the perfect itinerary for you. At Sand Dollar Charters, we pride ourselves on our personalized service and intimate knowledge of the local waters. Our fleet of modern, well-equipped vessels ensures a comfortable and safe journey, while our experienced crew is passionate about sharing the hidden gems and natural beauty of the Gulf Coast. From families and groups to couples looking for a romantic escape, we cater to all adventurers seeking to explore the vibrant marine life and pristine beaches of St. Pete Beach.

Welcome to Well Played Charters, your premier destination for unforgettable maritime adventures in the heart of St. Petersburg, Florida. Located at 3769 50th Avenue South, our unique charter service offers an exceptional way to explore the stunning waters of the Gulf Coast. Whether you're a fishing enthusiast, a wildlife lover, or simply seeking a relaxing day on the water, Well Played Charters promises a personalized experience tailored to your desires. Our knowledgeable and friendly crew is dedicated to ensuring your time with us is both enjoyable and memorable. With a fleet of well-equipped vessels, we provide a range of activities including deep-sea fishing, dolphin watching, sunset cruises, and more. Each trip is designed to offer a perfect blend of adventure and relaxation, showcasing the natural beauty and vibrant marine life of the region.

Welcome to HappySails.live, your premier destination for unforgettable sailing adventures in the beautiful coastal city of St. Petersburg, Florida. Nestled in the heart of the Sunshine State, our tourist attraction offers a unique blend of relaxation and excitement on the sparkling waters of Tampa Bay. At HappySails.live, we specialize in creating memorable experiences for locals and visitors alike. Whether you're looking to unwind with a leisurely cruise or seeking the thrill of a high-seas adventure, our expert crew is dedicated to ensuring your time on the water is nothing short of spectacular. Our state-of-the-art sailboats are equipped with all the amenities you need for a comfortable and enjoyable voyage.

Welcome to ONE Inn and Suites, your quintessential retreat nestled at the charming intersection of Bay Street NE and 6th Avenue NE in the historic Old Northeast neighborhood of St. Petersburg, Florida. Located at 635 Bay Street Northeast, our inn offers a serene escape with ten exquisite rooms and suites designed for comfort and luxury. Our accommodations include three elegant studio suites in the Carriage House and seven luxurious rooms in the main house, each featuring either a king or queen bed. Guests will enjoy en-suite bathrooms with large tubs and showers, ensuring a relaxing experience. We pride ourselves on providing high-quality bedding with high thread-count cotton sheets, plush down comforters, and ample pillows, complemented by fresh and fluffy cotton towels. Modern conveniences such as smart TVs, cable, high-speed internet, and in-room coffee machines are standard in every room.