5+ Bedrooms

Escape to paradise in a spacious 5-bedroom vacation home on Anna Maria Island, perfect for families or large groups seeking the ultimate beach getaway. Our luxurious beachfront rentals feature modern amenities, private pools, and stunning Gulf views, all within walking distance of the island's pristine beaches, top restaurants, and unique boutiques. Enjoy activities like kayaking, fishing, and cycling, or simply relax on the sugar-white sands. Book your dream Anna Maria Island vacation today and experience the best in coastal living with easy access to Tampa Bay and Sarasota attractions.

Properties Available 3 properties available
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsUnmatched Luxury Featuring a Private Dock, Heated Pool, Putting Green, Game Room, and Spacious Accommodations for an Unforgettable Beachside Escape4793 sq. ft.HIGHLIGHTS: - Prime Bayfront location with breathtaking sunrise and sunset
NEWLY LISTED NEWLY LISTED
NEWLY LISTED
This home just joined the Once Upon A Beach exclusive portfolio! This home had flooding and is working to be professionally and safely restored, newly furnished, and ready for guests for Summer 2025!
Ocean Sunrise
Ocean Sunrise
Bradenton Beach
$580.00 - $2,250.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 19 guests
Welcome to Family Tides!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsThis listing is for the entire home including both units for a total of 6 bedrooms, 4 bathrooms, and private heated pool and rooftop deck for your personal and private use only.2288 sq. ft.HIGHLIGHTS:- 2 Separate Homes in One!- Each one level c
2 Homes in 1! 2 Homes in 1!
2 Homes in 1!
ACTIVELY welcoming guests! This home has 2 separate units for one completely private home/outdoor space featuring 6 bedrooms. Need a smaller space? Just rent one unit and potentially share the pool with the other unit.
Family Tides
Family Tides
Bradenton Beach
$420.00 - $1,600.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 5 (7)
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.A newly constructed premier luxury home just across the street from the pristine sugary white sands of Anna Maria Island with views of the gulf from practically every
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$770.00 - $2,900.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (4)

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