Happy Island Cottage
From $405/night
Anna Maria Island, Florida
Welcome to our favorite corner of Anna Maria Island.
We’re a local family offering three places to stay: a private-pool home in Holmes Beach and the two sides of our cute beach duplex, just 60 steps from the Gulf. We live nearby, answer every message ourselves, and have been helping guests feel at home here since 2013.
Owner-managed since 2013 · 400+ guest reviews · No platform fees when you book direct
Why guests book direct with us
Same homes, same calendar, better math: no platform or service fees when you book direct; pick your dates and the full all-in price appears before you send a request, then compare the same dates on Airbnb or Vrbo, and you deal directly with the people who own and care for the homes. Returning guests get the full perks list: no reservation deposit, cancel-anytime flexibility, and our Best Returning Guests code, 20% off every direct stay. Details here.
Boat rides and extras
Dolphin and sandbar boat trips around Anna Maria Island, pool heating in winter, and extra cleans for longer stays are all things we can arrange. The full menu lives on the extras page. New to the island? Start with our local guides.
