Happy Island Cottage
From $405/night
Anna Maria Island, Florida
Three beach rentals. One owner. No middleman.
A private-pool home in Holmes Beach and two duplex units about 60 steps from the Gulf in Bradenton Beach. Owner-managed since 2013, licensed with the state and city, and rated 9.4 to 10 out of 10 on Vrbo and 4.8 to 4.9 on Airbnb across more than 400 reviews. Book direct and skip the platform fees.
Why guests book direct with us
Same homes, same calendar, better math: no platform or service fees when you book direct, typically 10 to 15% less all-in than 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.