Sky on Anna Maria
Sky on Anna Maria has four bedrooms, two bathrooms, and an elevator to the main level. Floor-to-ceiling windows frame the sky views from the kitchen and living areas. Outside, a private zen garden with mature trees and Adirondack chairs. The beach is across the street. Bikes on site for exploring the island's 7 miles of coastline. Pine Avenue restaurants and the pier are a short ride away.
Property details
What's here
Beach across the street
Steps from the sand, with direct beach access for paddleboarding or a quiet morning walk.
4 bedrooms, 2 bathrooms
Spacious layout with an elevator to the main living level.
Floor-to-ceiling windows
The kitchen and main living areas look out through full-height glass, keeping the sky in view.
Private outdoor space
A lush backyard with mature trees, natural shade, and Adirondack chairs.
Bikes included
Bikes on site for riding the island's coastline or heading to Pine Avenue.
Sold
This property has been sold. Contact us to learn about other Serendipity properties.
Exterior
Sky on Anna Maria
Interior
Living area
Interior
Kitchen
Interior
Dining
Interior
Bedroom
Interior
Bedroom
Interior
Bathroom
Outdoor
Garden
Outdoor
Backyard
Views
Sky views
More than a place to stay
Loved by travelers and hosts
4.9
1354 reviews
“We are already planning a trip to come back! This place is even better than the photos. The owners were so responsive, kind, and accommodating!”
Justice
Stayed in August 2026
“Everything about it was great. The view, the location, no complaints. We had a few issues with the paddleboards and the team responded within the hour. ”
Erika
Stayed in July 2026
“we will definitely be back. great view and amazing home.”
Ryan
Stayed in July 2026
“What an absolutely amazing place to stay! The house was super clean from top to bottom. It was well stocked with supplies that lasted for our entire stay. You are just steps away from the water and it’s incredible to basically have your own private beach. It’s a great spot to watch the sunset, especially from the upstairs balcony. The hot tub in the back of the house was excellent. The swimming pool is small but it doesn’t even matter because you are right on the beach and we spent all our time there. Having a 6 person golf cart available the whole time is a fantastic amenity. Just a beautiful house and top notch location. The best house we have ever rented and would definitely stay again. Highly recommend.”
Spencer
Stayed in July 2026
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