Waterfront Vacation Rentals in Bradenton and on Anna Maria Island

Waterfront vacation rentals in Bradenton and on Anna Maria Island: canal-, bay- and lakefront homes with Sarasota Bay and Longboat Key just to the south. Many have a private dock and direct water access, a heated pool, and open water a few minutes from the back yard — made for boaters, anglers, and anyone who would rather look at the water than at a parking lot.

Browse the available homes below, from canal-front pool houses near Holmes Beach and Cortez to lakefront retreats in northwest Bradenton. Each listing shows live availability, and reservations run through us rather than through a platform: the cleaning fee and Florida lodging tax are itemized before you confirm, and nothing is added between the quote and the total. If the water is not the priority, look at our pool homes, condos and pet-friendly rentals instead.

Frequently Asked Questions

Do your waterfront rentals have a dock?

Many of our canal- and bayfront homes include a private dock and direct water access. Check each listing for the specific details.

How close are waterfront homes to the beach?

It depends on the home. Our Anna Maria Island homes are within walking distance of the Gulf beaches. The others sit on the mainland in West Bradenton, a quick drive from the island and its beaches. Check the individual listing to see which one you are looking at.

Can I book a waterfront home directly?

Yes. Check live availability and book directly with us — no middleman fees, just hands-on local support.

Every waterfront home on this page is looked after locally and belongs to a client of our sales brokerage, Sea to Sky Realty. We handle the keys, the cleaning and the questions in between, in English or German.