Luxury Vacation Rentals on Anna Maria Island

Golden hour on Anna Maria Island. In the foreground are beautiful homes, while the ocean and sunset can be seen in the distance. The homes all have a lush, tropical feel - perfect for your next Anna Maria Island luxury vacation!

Anna Maria Island offers a serene escape with its white sandy beaches, crystal-clear waters, and relaxed, laid-back atmosphere. Our luxury vacation rentals on the island provide a perfect home away from home, whether you're seeking a cozy beachfront cottage, an elegant villa, or a spacious family-friendly retreat. Each property is carefully designed to offer comfort and convenience, with easy access to Anna Maria Island’s best attractions. Experience the beauty of Anna Maria Island and create lasting memories with Once Upon A Beach’s exceptional vacation homes. Immerse yourself in the ultimate island lifestyle with our premier rentals.

Looking to accommodate a specific number of guests? You can also browse our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.

At Once Upon a Beach, we treat every home as if it were our own and every guest like family. When you book your next vacation with us, you'll receive unparalleled service and a stress-free experience from our team of Anna Maria Island locals and experts. We're proud to be locally-owned and operated, and to provide you with a boutique and intimate style of care. We'd love to help you find your next vacation rental today!

Our 'She's Always Right' Anna Maria Island luxury vacation rental, a soft blue house with white trim and coral-colored doors. This property, along with many others, is pet friendly! There's no need to leave your furry friend at home. They deserve a pet vacation!

Check out our pet-friendly vacation rentals

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Vacation rental with a beautiful private pool, located at our Sea La Vie Beach House on the North End of Anna Maria Island. Close to everything, from Pine Avenue’s shops, Bayfront Park, and Gulf beaches, this house has it all.

Check out our private pool vacation rentals

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Aerial view of our AcquaLuxe property, and the surrounding area, at sunset. This waterfront luxury vacation rental on Anna Maria Island is one of many offered by Once Upon a Beach, and boasts a heated saltwater pool, private dock, chef’s kitchen, and top-tier amenities for an unforgettable coastal retreat.

Check out our waterfront vacation rentals

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40 properties available