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.

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.

Cozy Cottage

A compact Holmes Beach cottage for two, with a king bed, kitchenette and outdoor seating. The listing requires a 30-night minimum. It is attached to another home, but that home’s pool is not included. Pets are not permitted.

A 30-night minimum does not automatically mean a calendar-month booking or a discounted monthly rate. Enter your exact arrival and departure dates, then review the quote and any restrictions on arrival days.

If you are planning a winter or snowbird stay, check the dates you need before arranging travel. A home that is listed on the site may already be reserved for part of your proposed visit.

• Review laundry facilities, kitchen equipment and storage for luggage and groceries.
• Ask what is included in utilities, internet and any pool-heating arrangements.
• Check housekeeping arrangements, rubbish collection and how to report maintenance issues.
• Confirm visitor, parking and pet rules for the individual rental.
• Read payment deadlines and cancellation terms for the full stay.

For the West Bay condo, allow time for the HOA application and fee required at least 14 days before check-in. Ask the reservations team which steps you must complete and when approval is needed.

Choose your base around the journeys you will make often, such as grocery shopping, beach access or visiting friends. Our guide to the island’s three cities can help you compare locations.

Keep the management company’s contact details handy after arrival. Anna Maria Rentals markets homes from Florida Vacation Homes and other professional local managers; the company responsible for the property handles the specific stay arrangements described in your agreement.