Four Bedroom Family Homes
Discover our curated collection of 4 bedroom homes on Anna Maria Island, designed for elevated group stays with refined coastal comfort. These spacious homes feature designer interiors, private amenities, and beautifully appointed indoor and outdoor living spaces.
Perfect for families and group getaways, each home delivers a boutique experience where every detail is intentional and every stay feels like your own island retreat.
14 properties available
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere calm meets connection, Serenity Now offers spacious living, modern comforts, and a private backyard oasis with a heated pool. Thoughtfully designed for ease and bal
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep into Three Little Birds — a bright, joyful island home designed for gathering, connecting, and letting the days unfold naturally. With Gulf views, a privat
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Bateman’s — where thoughtful design and waterfront living come together.Set along a quiet canal on Anna Maria Island’s north end, this modern coastal h
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island liv
Welcome to Vela Mar!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceVela Mar is where elevated coastal living meets modern luxury innovation. Designed with intention and inspired by the sophistication of Miami-style smart living, this fully i
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units: Island Girl East & Island Girl West*The SpaceWith room for up to 10 guests, Island Girl East & West is thoughtfully designed for shared experiences and easy island living. Each side of t
Welcome to The Curated Palm!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceThe Curated Palm is a home that feels at once elevated and effortless — where thoughtful craftsmanship, inspired design, and island living align in perfect h
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
Welcome to Sunset at 714!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceWhere island sunsets, beach days, and family memories come together.Tucked away on the highly desirable north end of Anna Maria Island, Sunset at 714 places you just a short stroll from the sugar-whit
Welcome to Cortez Dock & Dine!On Florida’s Gulf Coast (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A rare waterfront escape blending Old Florida charm with modern coastal living.Please note: Boat not included with rental. For more information about boat rental
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere thoughtful design meets island energy, She’s Always Right blends modern artistry, resort-style comfort, and an unbeatable location just steps from t
Welcome to Casa Mariposa!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Casa Mariposa where the rhythm of island life slows, and beauty unfolds in every detail. Just one street north of Pine Avenue and four houses from the beach, this elegan
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