Five+ Bedroom Vacation Rentals

The rooftop deck of our Anna Maria Island luxury vacation rental, Mariner's Crossing. In the foreground are Adirondack chairs on the rooftop deck, looking out over several homes and the beautiful beach and ocean. This retreat is just off of Pine Avenue, and is perfectly located near all of Anna Maria Island’s top attractions.

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.


Waterfront Rentals

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.


Pet friendly rentals

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.


Private pool rentals
Properties Available 3 properties available
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsThe SpaceSet directly on the Bay in Bradenton Beach, Ocean Sunrise offers 4,793 square feet of bright, inviting living. The design balances elegance and ease—sun-filled rooms, expansive gathering spaces, and a backyard where the lin
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Ocean Sunrise
Ocean Sunrise
Bradenton Beach
$700.00 - $2,500.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 20 guests
Rating 5 (1)
Welcome to Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Where gathering comes naturally and every generation finds its place in the sun.Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers
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Family Tides
Family Tides
Bradenton Beach
$450.00 - $1,700.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 4.8 (9)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
Hot HOT 57
Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$800.00 - $3,500.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (12)

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