Naples, FL is a true haven for boating enthusiasts and water lovers alike. Nestled along Florida’s picturesque southwestern coast, Naples captivates visitors with its stunning waterfront enclaves and a wealth of recreational opportunities. Among its gems is Winterwind – A Water Lover’s Dream, a luxurious waterfront retreat by Rozel Homes. Our exceptional vacation rental features multiple open-air lanais, a heated pool, a delightful mini-golf course, and direct Gulf access with a state-of-the-art dock and hydraulic boat lift. Whether you’re a boat owner seeking the perfect home base or a family eager to embrace the boating experience during your stay, Winterwind offers an unparalleled haven for anyone seeking to set sail and immerse themselves in Naples’ aquatic wonders.
Naples’ year-round pleasant climate and crystal-clear waters make it an ideal location for various boating adventures. You can leisurely cruise along the peaceful canals or take exhilarating trips into the Gulf of Mexico. Our guide to boat rentals and charters in Naples, FL will take you on a journey to explore the marine wonders, stunning coastal vistas, and a wealth of water sports that await you. Whether you have prior boating experience or not, Naples’ nautical charm will create memories that will last a lifetime. Join us as we discover the best boat rental and charter options that Naples has to offer.

The Perfect Climate, Calm Waters, and Navigable Channels
Nestled in a region blessed with an idyllic climate, Naples offers boating opportunities year-round. Its mild winters and warm summers create an inviting environment for boaters to explore its serene waters whenever they desire. With clear skies and pleasant temperatures, every day presents an opportunity for unforgettable boating adventures.
Naples’ waterways boast calm and clear waters, including its peaceful canals and expansive bays. The tranquil channels offer a smooth and enjoyable boating experience, making it an ideal destination for seasoned sailors and newcomers to the nautical world. Whether seeking a leisurely cruise or an exhilarating ride, Naples’ navigable waters cater to all preferences.
Diverse Array of Watercraft Rental and Charter Options
In Naples, a plethora of watercraft options are available for rent or charter, ensuring that every boating enthusiast finds their perfect vessel. From luxurious yachts to sleek speedboats, pontoon boats, and family-friendly catamarans, the choices are as varied as the interests of those embarking on the water adventures.
For experienced boaters, Naples provides opportunities to captain their own vessels, navigating the city’s waterways at their leisure. Meanwhile, those new to boating can opt for guided tours or rent boats with skilled captains who can lead them to the most captivating spots along the coast.
Whether you’re an avid seafarer seeking a new maritime paradise or a curious explorer yearning to discover the beauty of the Gulf Coast, Naples, FL, promises an unforgettable boating experience for all.

Top Boat Rental and Charter Companies in Naples, FL
When it comes to boating in Naples, FL, the options are abundant, and the experiences are unparalleled. Even if you can’t bring your own vessel on vacation or are new to the boating scene there are a plethora of boat rental and charter options available to explore the picturesque waterways and the Gulf of Mexico’s crystal-clear waters. Here are some of the top boat rental and charter companies in the area:
Pure Florida
Pure Florida is a family-owned and operated boat rental company in Naples, specializing in water experiences that showcase the beauty and wonder of Southwest Florida. They offer a wide range of activities for all ages, including sightseeing and sunset cruises, Jet Ski tours and rentals, boat rentals, fishing trips and charters, eco-tours, jet boat thrill rides, and private family and corporate cruises. Recently recognized as the best family-fun activity, overall attraction, sightseeing tour, watersport rental, and fishing charter by Gulfshore Life’s Reader’s Choice Awards, Pure Florida provides numerous ways to “seas the day.”
For guests wanting to take a guided cruise Pure Florida tours are known for scenic views, friendly and informative crew, and overall enjoyable experiences. During the trips, Captain Megan and First Mate Katie offer insights into the local ecosystem and wildlife. Visitors can spot dolphins and collect beautiful shells while exploring the picturesque waters. Overall, Pure Florida stands out as a must-do activity during a trip to Naples, providing an unforgettable and refreshing boating experience.
Island Sailing
Embark on an unforgettable sailing adventure with Island Sailing. They offer a variety of private sailing experiences, from romantic sunset cruises to week-long journeys along Florida’s southwest coast, even down to the Florida Keys, Island Sailing caters to every customer’s needs. Encounter playful dolphins and enjoy nature and bird watching with their captained crew. Whether you choose the spacious Island Time (47′ Beneteau) or the nimble Island Dreams (31′ Catalina), their vessels are well-equipped for a seamless and enjoyable sail. Captain Marty and Captain Paul will ensure you have an exceptional and top-notch experience aboard their yachts. For a unique perspective of Naples’ stunning coastline and sugar-white sand beaches, set sail with Island Sailing for a sailing adventure that will leave you in awe.
Naples Bay Resort Boat Rentals
With Naples Bay Resort Boat Rentals you can treat your family to an unforgettable day on the water. Conveniently located at the Naples Bay Resort and Marina near Downtown Naples, their boats come equipped with large coolers and full USCG safety equipment, ensuring a safe and enjoyable adventure. Their friendly and knowledgeable staff go above and beyond by providing 5-star service from valet parking to helpful instructions and suggestions. The boats are well-maintained and perfect for exploring Keewaydin or other local waters, swimming, fishing, and sunbathing. George, Hugo, and the entire staff ensure a seamless and enjoyable boat rental experience. Whether you’re a first-time renter or an experienced boater, Naples Bay Resort Boat Rentals is your go-to choice for a fantastic day on the water.
Naples Jet Ski Rental
Naples Jet Ski Rental has been the #1 Jet Ski rental company in Naples, Florida, since 2012, offering thrilling and safe water adventures. They take pride in prioritizing safety while ensuring an amazing time on the water. Their “Ski Like You Stole Em” Tour is a top-ranked experience, taking riders on a 3-hour journey through backwater mangroves and into the Gulf of Mexico. Along the way, you can spot dolphins, rays, and tropical birds, with a stop at Keewaydin Beach for a quick swim and some free play. For those who prefer a private ride, their Self-Guided Jetski Rentals provide over 20 miles of riding area—the largest in Southwest Florida! The staff are friendly and knowledgeable, their equipment is top-notch, and their scenic routes offer a refreshing change of scenery. Naples Jet Ski Rental ensures a memorable and enjoyable experience for every rider.
Captain Joey D Charters and Boat Rentals
Joey D Boat Rental offers an exceptional boating experience in Naples, catering to both experienced boaters and beginners. With a variety of boat options available, from 2022 23ft Starcraft Tritoons to private fishing charters, guests can explore Naples’ secluded waterways and abundant wildlife. The rental process is seamless, and the staff is friendly and helpful, ensuring a memorable and carefree boating adventure. Boats are well-maintained boats and come equipped with helpful maps, allowing guests the freedom to explore Keewaydin Island and other picturesque spots. Joey D Boat Rental is a go-to choice for an unforgettable day on the water for families and water enthusiasts.
Naples Extreme Family Fun Spot
Extreme Rentals in downtown Naples offers many exciting activities and rentals for visitors and locals alike. With options including Segway PT Tours, Pontoon and Deckboat Rentals, Kayak and Paddleboard Rentals, and Bike Rentals, there’s something for everyone to enjoy. For those seeking a more adventurous experience, they also provide Fishing Charters and private boat cruises. The friendly and efficient staff ensures a seamless rental process, making it a perfect place to bring your family for a day of fun activities. The boats are well-maintained and the dock staff are extremely helpful, thus creating unforgettable memories for all who visit Extreme Rentals in Naples.
Park Shore Marina
Park Shore Marina in Naples offers a great selection of high-quality rental boats, making it a sought-after choice for boating enthusiasts on vacation. Conveniently situated behind the “M” Waterfront Grill, the marina provides easy access to the waters of Venetian Bay. Apart from boat rentals, they also offer fuel services and custom charters. Their ships store is well-stocked with essentials like frozen and live bait, tackle, beverages, and sundries. The boats are in pristine condition and the staff are always friendly and helpful, ensuring a delightful boating experience for Rozel guests. Park Shore Marina is a go-to destination for boat rentals in Naples.
Boat Naples
Boat Naples offers extraordinary boat tours and charters, providing a unique and memorable experience on the waters of Naples, Bonita Springs, Estero, and Fort Myers. With private guided tours, guests can explore the Gulf of Mexico and the Inter-coastal waterways, observing dolphins and the stunning Florida birdlife. The tours include sunrise/sunset cruises, eco-tours, beach picnics and shelling, and dolphin watching, making it a versatile and enjoyable boating experience for all. Captain Sondi, known for her knowledge and friendliness, ensures a delightful journey for her guests, sharing interesting historical insights along the way. You can admire the beautiful beach from the water and see the magnificent homes, creating unforgettable memories aboard Boat Naples.
Port of Naples Marina
The Port of Naples Marina offers a variety of exciting boating experiences. For fishing enthusiasts, there are options to charter fishing boats for deep sea, backwater, offshore, and sport fishing, accommodating both private and group trips.
For those seeking a leisurely cruise, the Naples Princess and Miss Naples offer public and private cruises. The Naples Princess is a luxurious 105′ yacht with air-conditioned salons and outdoor areas, while the Miss Naples is a custom sailing catamaran for a more intimate experience. These cruises showcase the stunning sights of Naples Bay and Port Royal, including beautiful homes and natural wonders.
Additionally, visitors can enjoy boat rentals featuring brand-new deck boats and pontoons, perfect for relaxing cruises along Naples Bay, Marco Island, and the Ten Thousand Islands. Rentals are available by the hour, half-day, or full-day.
The marina provides a range of services and amenities, making it a go-to destination for boating enthusiasts in Naples.
South Bay Marina
South Bay Marina offers a range of exciting boating and fishing experiences. Guests can enjoy sightseeing cruises, explore the waters on their own with boat rentals, or embark on deep sea fishing adventures.
The marina’s boat rentals feature pontoons, bow riders, and center console boats, catering to various preferences and needs. They offer options for exploring mangrove forests or cruising the near-shore waters of the Gulf.
South Bay Marina provides offshore deep-sea fishing and nearshore backwater fishing charters for fishing enthusiasts. During different seasons, guests can target a variety of species, from grouper, snapper, and redfish to tarpon, shark, and snook.
Guests have praised their experiences at South Bay Marina, with reviews highlighting the professionalism and knowledge of the captains, as well as the abundance of fish and memorable catches during the trips. The marina caters to groups of friends and family members of all ages and experience levels, ensuring a delightful and enjoyable time on the water.

Navigating Naples’ Waters from Your Luxury, Waterfront Vacation Rental
Naples, FL, is without a doubt a paradise for boating enthusiasts and water lovers. For those looking to experience the ultimate aquatic getaway, Winterwind – A Water Lover’s Dream by Rozel Homes provides a luxurious waterfront retreat with Gulf access, a heated pool, and premiere amenities, making it the perfect home base for an unforgettable boating adventure.
Naples’ year-round pleasant climate and calm waters make it an ideal destination for boating year-round. Whether you’re a seasoned sailor or a newcomer to boating, the city’s navigable channels and serene waterways cater to all preferences, ensuring a smooth and enjoyable experience for everyone. And when it comes to boat rentals, Naples offers an array of watercraft options to cater to every taste. From luxurious yachts to family-friendly pontoons and guided tours, visitors can explore the picturesque waterways and the crystal-clear waters of the Gulf of Mexico. Each boat rental company brings its unique charm and top-notch service, ensuring guests have an unforgettable and refreshing time on the water.
When planning your next vacation in Naples, make sure to book a stay at Winterwind – A Water Lover’s Dream by Rozel Homes, a luxurious waterfront retreat that offers the perfect launching point for your boating adventures. Whether you choose to rent a boat and explore the waters on your own or embark on guided tours with experienced captains, Naples’ nautical charm will create lasting memories for you and your loved ones.