Happy Island Cottage
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 4.8 to 4.9 across hundreds of stays. Book direct and save 5%.

Happy Island Cottage: private heated pool home in Holmes Beach, Anna Maria Island

Happy Island Cottage

Private-pool home in Holmes Beach
Sleeps 6 · 3 BR · 2.5 BA · ★ 4.93 (75 reviews)
From $425/night
Happy Turtle A: beach duplex about 60 steps from the Gulf in Bradenton Beach

Happy Turtle A

60 steps from the beach, Bradenton Beach
Sleeps 5 · 2 BR · 1.5 BA · ★ 4.88 (56 reviews)
From $289/night
Happy Turtle B: beach duplex about 60 steps from the Gulf in Bradenton Beach

Happy Turtle B

60 steps from the beach, Bradenton Beach
Sleeps 4 · 2 BR · 1 BA · ★ 4.77 (81 reviews)
From $289/night

Why guests book direct with us

Same homes, same calendar, better deal: no platform service fee, 5% below our listed nightly rates for booking direct, and you deal directly with the people who own and care for the homes. Returning guests get extra perks, including reduced deposits and flexible cancellation. Details here.

Boat rides and extras

Dolphin and sandbar boat trips around Anna Maria Island, pool heating in winter, extra cleans for longer stays, and airport pick-up are all things we can arrange. Ask when you book: the extras menu is growing this season.