Does Happy Island Cottage have a private pool?

Yes. The pool is private to the home. Pool heating is available from roughly October through April for an additional fee.

How far is the beach from Happy Island Cottage?

About 0.3 miles: roughly 400 steps, a 5 to 6 minute walk at a normal pace to the Gulf beaches of Holmes Beach.

Is Happy Island Cottage pet friendly?

Yes, dogs are welcome with a pet fee. Tell us about your pet when you request dates.

What are check-in and check-out times?

Check-in is 3:00 PM, check-out is 11:00 AM. Early check-in and late check-out can sometimes be arranged around the cleaning schedule.

Holmes Beach, Anna Maria Island, FL

Happy Island Cottage

A two-story, three-bedroom pool home in Holmes Beach on Anna Maria Island. Sleeps 6 in 4 beds with 2.5 baths, private heated pool, pet friendly, and a 5 to 6 minute walk (0.3 miles) to the Gulf beach. Rated 4.93 from 75 reviews.

Airbnb Guest Favorite
Superhost host, 15 straight quarters
Private heated pool
5 minute walk to the beach

Happy Island Cottage front exterior: two-story coastal home with palms, Holmes Beach

Private pool and sun deck behind Happy Island Cottage

Covered poolside patio with outdoor dining, Happy Island Cottage

Happy Island Cottage and pool lit up at dusk

Open living and dining room, Happy Island Cottage

The facts

Sleeps	6 guests
Bedrooms	3 (4 beds)
Bathrooms	2.5
Nightly rate	From $425, up to $650 in peak season. Direct bookings: 5% off these rates.
Guest rating	★ 4.93 from 75 Airbnb reviews (as of July 2026)
Check-in / out	3:00 PM / 11:00 AM
Pets	Dogs welcome, pet fee applies
Location	Holmes Beach, Anna Maria Island, Florida 34217

Amenities

Private heated pool (heating available October to April)
About a 5 to 6 minute walk to the Gulf beach (0.3 miles)
Impact-rated windows and doors throughout
New metal roof (2025)
Central air (new 2024 system, Nest thermostat)
Fast Wi-Fi
Pet friendly (fee applies)

Availability

Checking live availability. If the calendar does not load, email us your dates and we answer same day.

One calendar across Vrbo, Airbnb, and direct stays. Checkout days are open for new check-ins.

Book Happy Island Cottage direct

Email us your dates and we confirm availability the same day, usually much faster. Direct guests get 5% below our listed nightly rates for booking direct, and returning guests do even better.

Request dates by email How direct booking works

Prefer the platforms? The same calendar lives on Airbnb and Vrbo. Florida and Manatee County lodging taxes (13%) are itemized on every direct invoice.

Good to know

Does Happy Island Cottage have a private pool?: Yes. The pool is private to the home. Pool heating is available from roughly October through April for an additional fee.
How far is the beach from Happy Island Cottage?: About 0.3 miles: roughly 400 steps, a 5 to 6 minute walk at a normal pace to the Gulf beaches of Holmes Beach.
Is Happy Island Cottage pet friendly?: Yes, dogs are welcome with a pet fee. Tell us about your pet when you request dates.
What are check-in and check-out times?: Check-in is 3:00 PM, check-out is 11:00 AM. Early check-in and late check-out can sometimes be arranged around the cleaning schedule.

Licensed vacation rental, operated by Happy Island Cottage LLC. Florida and Manatee County lodging taxes (13%) are itemized on every direct invoice.