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.

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.

Looking for cozier vacation rental options? We also offer 2 Bedroom, 3 Bedroom, 4 Bedroom, and 5+ Bedroom luxury vacation rentals.

Vacation rentals by amenity

Pet friendly vacation rentals        Private pool vacation rentals        Waterfront vacation rentals

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 EscapeHIGHLIGHTS: 4,793 sq. ft. of luxurious living space Prime Bayfront location with
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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 (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Elevate your vacation experience at Family Tides, a beautifully renovated coastal retreat featuring two stacked condo-style homes, offering a total of 6 bedroom
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Family Tides
Family Tides
Bradenton Beach
$540.00 - $1,600.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 5 (8)
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.Discover coastal elegance at Mariner's Crossing, a premier luxury vacation rental home just steps from the pristine, sugary white sands of Anna Maria Is
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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 (6)

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