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Welcome to Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Set on a quiet street near the sand, Mango Bay blends open interiors with plenty of outdoor living. Upstairs, the main living floor brings kitchen, dining, and lounge spaces together
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 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 Hangin’ on Hammock!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 pool and spa are currently under construction and are scheduled for completion by May 2026. Construction is set to begin January 1, 2026. Because the po
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 Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.Nestled on the peaceful North End of Anna Maria Island, just 500 feet f
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 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
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 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 Fins Up!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 SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
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
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