Three Bedroom Vacation Rentals
Our collection of 3 bedroom homes on Anna Maria Island is designed for families and small groups seeking space, comfort, and a seamless island experience. Each home offers thoughtfully styled interiors, inviting outdoor living areas, and close proximity to the island’s beautiful beaches.
Whether you’re gathering for a family getaway or a relaxed coastal retreat, these homes provide the perfect balance of connection and privacy, all within the elevated, boutique experience of Once Upon A Beach.
14 properties available
Welcome to The Palm at Bean Point!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsWhere modern luxury meets laid-back island living, just moments from Bean Point.Tucked away in one of Anna Maria Island's most beloved neighborhoods, this beautifully renovated coastal retreat offers everything you need for a rela
Welcome to Coconut Lagoon!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 Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike
Welcome to AMI Peppertree Paradise!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 AMI Peppertree Paradise — a light-filled beach home where mornings begin with salt air and end beneath the glow of island skies.Just three houses from th
Welcome to Family Tides – Unit A!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides A (Bottom Unit)*Located just steps from the Gulf of Mexico and walkable to Bridge Street, this ground-level unit invites you to unwind, connect, and enjoy a thoughtfully
Welcome to A Wave From It All!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 A Wave From It All — a single-level island home crafted for connection and carefree living. Tucked on the quiet north end of Anna Maria Island, this pet-frien
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
Welcome to Sandy Pants!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 creativity meets coastal calm, Sandy Pants brings modern design and island ease together just steps from the Gulf. Every detail feels intentional — from the na
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceThoughtfully redesigned for simplicity and comfort, On Turtle Time blends the charm of an island cottage with the ease of modern living. Inside, natural light filt
Welcome to Sea La Vie!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 light dances across the water and modern design meets island ease, Sea La Vie invites you to experience the beauty of Anna Maria Island from a space that feels both lux
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