The Best Family sailing vacations in Santa Rosa Beach, Florida

Resortquest by Wyndham Vacation Rentals is a real estate and travel agency located at 731 Pensacola Beach Boulevard in Pensacola Beach, Florida, United States. Our Pensacola Beach house rentals and condos offer a unique and relaxing island experience where the sand and sun come together. The community features modern high-rises and white sand dunes, providing a haven for sunbathers, whale watchers, and deep-sea fishermen. Whether you're exploring the Footprints in the Sand Echo Trail, riding jetskis with Radical Rides, or simply relaxing on the beach, this friendly community is perfect for your next Sunshine State getaway. Our Pensacola Beach vacation rentals cater to every type of traveler. We offer dog-friendly homes, properties with internet access, and professional housekeeping services to ensure a comfortable stay. Located on Santa Rosa Island, just south of Pensacola, our rentals provide easy access to the Gulf of Mexico and the Gulf Islands National Seashore. Guests can enjoy sailing, fishing, swimming, snorkeling, and diving in the warm, clear waters of the Gulf. The Pensacola Beach Boardwalk, Quietwater Beach, and nearby attractions offer plenty of entertainment options for visitors.

Wildwind Charters, located at 1689 North County Highway 393 in Santa Rosa Beach, Florida, offers unforgettable experiences on the water. With a 26′ Searay Sundeck and a 26′ Avalon ‘Tritoon’ that can accommodate up to 10 passengers each, we cater to family outings, corporate gatherings, engagement parties, and cocktail parties. Explore popular destinations such as Crab Island, the Destin Harbor, and the Choctawhatchee Bay on our 8-hour cruise, which includes stops at Shell Island, the Intercoastal Waterway, and Crab Island. For those looking for a more customized experience, we also offer charters by the hour.