Under contract-accepting backup offers. Island living meets proven vacation-rental performance in this beautifully maintained Holmes Beach home! Whether you're searching for your own Anna Maria Island retreat or an established income-producing property, this home offers the rare combination of tropical privacy, generous indoor and outdoor living space, and an impressive history as a successful vacation rental. Currently licensed for short-term rental use with the City of Holmes Beach, the property allows a minimum 7-night stay and comes with something particularly valuable to an investor: an established rental history, repeat clientele and bookings already extending into 2027. The home has earned an exceptional 10/10 rating on VRBO from 163 guest reviews, with guests repeatedly praising the pool and spa, cleanliness, comfortable accommodations, well-stocked home and easy walk to the beach. Some returning guests have vacationed here for nine years-and have already booked again for 2027. The home itself was made for the Florida lifestyle. Bright, comfortable living spaces flow easily into multiple outdoor areas, while the lush tropical surroundings create a wonderful sense of privacy. The expansive covered lanai provides an incredible amount of room for dining, entertaining and relaxing out of the Florida sun, while the upper covered balcony offers another peaceful spot surrounded by palms. At the heart of the outdoor experience is the private saltwater pool and spa, beautifully tucked into the tropical landscape and featuring a specially designed non-slip surface. The pool has been exceptionally well maintained, with a new heater installed in October 2024 and additional equipment updates and a comprehensive maintenance review completed in 2026. Remote Pentair ScreenLogic controls allow the pool and spa to be managed from virtually anywhere. Inside, the spacious kitchen offers abundant cabinetry and counter space and opens to the main gathering areas which boasts twelve foot high ceilings, enhancing the feeling of space and light in the dining and living areas. The primary suite includes a generous bath with dual vanities, soaking tub and separate walk-in shower, while additional bedrooms provide comfortable accommodations for family and guests. Thoughtful ownership is evident throughout, including two modern and meticulously maintained HVAC systems, with the main-level Lennox installed in 2022 and the upper-level Trane installed in 2018, along with numerous recent appliance, mechanical and equipment updates. Remote thermostat access makes managing the property especially convenient for an owner who may not live locally. The property also holds a current Holmes Beach Rental Certificate valid through May 2028 and successfully completed its 2026 West Manatee Fire & Rescue inspection. HOA fees include several significant ownership expenses, including flood and property/casualty insurance, grounds maintenance, trash removal, pest and termite treatment, exterior maintenance, irrigation and backflow testing. Come for the island lifestyle-or step into a turnkey furnished vacation property with a track record already in place. Either way, this is a home designed to make the most of life on Anna Maria Island.