ANNA MARIA ISLAND • STAY PLANNING
Anna Maria Island Rentals with Pools
A pool can make the hours between beach trips easier: a swim before breakfast, a quiet afternoon at the house or somewhere to cool off after exploring the island. Start with the homes below, then check the pool arrangements and availability for your dates.
Choose your pool setting
A private pool belongs to the home you are renting. A community pool is shared with other residents and guests, and may have set opening hours or additional rules. Neither description tells you whether heating is included in the booking total.
The distinction matters when you compare a large waterfront house with a condo. Decide whether you want a pool immediately outside your door or are happy to walk to a communal pool in exchange for a smaller place to stay.
Listed rentals with pool access
Happy Place
A canalfront home in Holmes Beach with six bedrooms, space for up to 12 guests and a private screened pool. The separate guest apartment gives part of the group its own kitchen and living space. The listing requires a 30-night minimum stay.
Island Life Villa
Five bedrooms accommodate up to 10 guests across a main house and attached guest residence, rented together as one property. There are two kitchens, a waterfront deck and a heated pool. A seven-night minimum and seasonal arrival rules apply; check the calendar for your trip.
West Bay Point & Moorings, Unit 85
This two-bedroom Holmes Beach condo overlooks the bay and has access to a shared heated pool. It has two king beds and sleeper accommodation, with a stated maximum of six guests. A 30-day minimum applies. The listing requires an HOA application and fee at least 14 days before check-in.
Check heating and access before booking
- Ask whether pool heating is included, optional or subject to an additional charge.
- Check the heating policy for cool weather. A heated pool is not a promise of a particular water temperature.
- Review pool access, steps, barriers and the route from bedrooms or living areas if children are travelling.
- Confirm any shared-pool hours, guest restrictions or planned maintenance.
Photos are useful, but the property’s current description and rental agreement should settle what is included. Contact the reservations team if the two appear to disagree.
Match the home to your trip
Happy Place suits a month-long stay for a larger party, while Island Life Villa has a shorter listed minimum. The West Bay condo offers a smaller waterfront base with shared facilities. Compare sleeping arrangements as well as the maximum guest count.
Anna Maria Rentals features homes managed by Florida Vacation Homes and other professional local companies. Pool services and booking policies vary by property. See the individual listing for the company responsible for your stay.
Questions before you book
Are all these pools private?
No. Happy Place and Island Life Villa list private pools. West Bay Point & Moorings Unit 85 has access to a shared heated pool.
Does every rental on the website include a pool?
No. For example, Cozy Cottage does not include access to the pool at the adjoining home. Check the exact listing you intend to book.
Can I book a pool home for a week?
Island Life Villa lists a seven-night minimum, with seasonal arrival rules. Happy Place requires at least 30 nights. Dates remain subject to availability.