Five+ Bedroom Vacation Rentals

Indulge in the ultimate island escape with a spacious 5+ bedroom vacation rental on Anna Maria Island, perfect for families or groups seeking refined coastal living. These stunning homes feature designer interiors, private pools, and sweeping Gulf views, all just steps from the island’s pristine beaches, fine dining, and boutique shopping.
Savor unforgettable days kayaking, fishing, or cycling along the shoreline, or simply unwind on sugar-white sands under the Florida sun. For a more intimate retreat, explore our exclusive 2-, 3-, and 4-bedroom luxury vacation rentals tailored to every style of getaway.
Explore the collection of waterfront vacation rentals on Anna Maria Island and find your perfect beach getaway. Wake up to breathtaking views, unwind in style, and experience the best of island living.
Browse our pet-friendly vacation rentals on Anna Maria Island and discover the perfect beach home for you and your furry friend. Enjoy easy access to the island’s top beaches, dining, and attractions.
View our selection of vacation rentals with private pools on Anna Maria Island. Enjoy a refreshing dip any time of day, spacious outdoor living areas, and the perfect blend of relaxation and island charm.
Tell us what you're looking for and someone will contact you with available options.