Anna Maria Island Rentals with a Pool

Browse Anna Maria Island rentals with private pools for a swim before breakfast, an afternoon at the house, or time outdoors after the beach. The collection includes two-bedroom rentals, larger family homes, and properties with separate living areas for groups staying together. Choose a location near Gulf beaches, on the bay, or along a canal, then compare the pool and outdoor features that matter to your stay.

A private pool gives your group a place to gather without sharing a resort swimming area. Many properties also have outdoor dining tables, covered seating, and grills, making it easy to spend more of your vacation at the rental.

Pool features vary across the collection. Beach Pearl has three bedrooms, a heated saltwater pool, a spa, and covered outdoor dining. Fairwinds offers four bedrooms, a heated pool with a swim-up bar table, a hot tub, and an outdoor kitchen.

For a smaller group, Sugaree is a two-bedroom duplex rental with a private heated pool and a covered lounge with a TV. Larger groups can consider Dodt House units 1, 2, and 3, a beachfront triplex rented together with a heated beachside pool and sun shelf.

Some homes also welcome dogs. Browse our Anna Maria Island dog friendly rentals, then check each listing for pool amenities and pet policies.

As you compare Anna Maria Island vacation rentals with pools, review:

• Pool heating: Confirm heating availability for your dates. Weather can affect water temperatures, and a heated pool does not guarantee a specific temperature.

• Pool layout: Look for listed features such as sun shelves, sitting ledges, or screened enclosures.

• Spas and hot tubs: Check the listing if you want one alongside the pool.

• Outdoor amenities: Compare shaded seating, dining areas, grills, and outdoor showers.

• Rental arrangements: For duplexes or properties rented as multiple units, confirm who has access to the pool.

Browse available dates and book an Anna Maria Island rental with a private pool that fits your group. Contact our vacation specialists if you need help confirming pool features or choosing a property.