Happy Island Cottage
A week from $2,321.02 all in: rent, cleaning and taxes included, no fees
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
Happy Turtle A
3 nights from $1,024.91 all in: rent, cleaning and taxes included, no fees
Happy Turtle B
3 nights from $1,024.91 all in: rent, cleaning and taxes included, no fees
The three homes side by side
| Happy Island Cottage | Happy Turtle A | Happy Turtle B | |
|---|---|---|---|
| Where | 312 57th St, Holmes Beach, FL 34217 | 2303 Avenue C, Bradenton Beach, FL 34217 | 2303 Avenue C, Bradenton Beach, FL 34217 |
| Type | House, 3 bedrooms, 2.5 baths | One side of a beach duplex, 2 bedrooms, 1.5 baths | One side of a beach duplex, 2 bedrooms, 1 bath |
| Sleeps | 6 guests | 5 guests | 4 guests |
| Standout | Private heated pool, heated November through April, included in the rate | About 60 steps to the beach, with a private entrance and yard | About 60 steps to the beach, with a private entrance and yard |
| Minimum stay | 7 nights, a City of Holmes Beach rule | 3 nights when you book direct | 3 nights when you book direct |
| Dogs | Dogs are welcome at all three homes: up to two per stay, no size limit, $199 per stay plus tax, waived for returning direct guests. | ||
| Check in and out | Check in 3:00 PM, check out 10:00 AM, at all three homes. | ||
| How to book | Pick your dates on a home's page to see the all in price, then send the request. We confirm by email with a secure payment link: 20% at booking and the balance 45 days before arrival, or payment in full when arrival is 45 days away or less. Sending a request does not hold your dates: they are reserved when the deposit or full payment clears. | ||
| Questions | Call or text 941-928-0036, or email info@happyislandcottage.com. The owners answer. | ||
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, extra cleans for longer stays, and more are all things we can arrange. The pool at Happy Island Cottage is heated November through April, included. The full menu lives on the extras page. New to the island? Start with our local guides.
