Happy Island Cottage
Welcome to our dream island cottage. It took years to find a gem like this, and we love it enough to sneak in ourselves whenever the calendar has a gap. :) 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 10/10 on Vrbo and 4.93 on Airbnb.
- Airbnb Guest Favorite
- Superhost host, 15 straight quarters
- Private heated pool
- 5 minute walk to the beach
About this home
Your own heated pool, a five-minute walk to the Gulf, and the whole house to yourselves in quiet Holmes Beach. We are one of the few family-run homes left on the island, we answer our own messages, and so many of our guests come back year after year.
A modern two-story cottage that sleeps six, with a private fenced pool, two decks, and a garage full of beach toys and a wagon left for you to borrow. Leave the car parked: it is a short walk to the beach, the marina, the shops, and the Ugly Grouper.
Traveling as a bigger group, or want to be right on the sand? Happy Turtle A and Happy Turtle B, our two cottages sixty steps from the beach in Bradenton Beach, are ten minutes up the island.
There is a paper guest book on the kitchen counter, and guests have been filling it for years. We scanned the pages: read their handwritten notes. (The booking platforms will not let us reprint the reviews you wrote on their sites. The notebook has no such rules.)
The facts
| Sleeps | 6 guests |
|---|---|
| Bedrooms | 3 (4 beds) |
| Bathrooms | 2.5 |
| Nightly rate | From $405 to $650 a night by season. Booking direct adds no platform or service fees. |
| Guest rating | 10/10 from 98 Vrbo reviews · 4.93/5 from 75 Airbnb reviews |
| Guest book | 43 handwritten reviews from our paper guest book, scanned and transcribed word for word |
| Check-in / out | 3:00 PM / 10:00 AM |
| Minimum stay | 7 nights, a City of Holmes Beach rule |
| Pets | Dogs welcome, pet fee applies |
| House rules | Checkout instructions, parking, pets, quiet hours, trash days: the full house rules |
| Location | 312 57th St, Holmes Beach, Anna Maria Island, Florida 34217 |
Amenities
- Pet friendly
- 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 fancy ocean wave looking metal roof
- Central air
- Fast Wi-Fi
Alex & Elena, owners and your hosts since 2013. Questions before you book? 941-928-0036, call or text.
Verify us where you already have an account: this home on Airbnb (4.93/5, 75 reviews) or on Vrbo (10/10, 98 reviews). Licensed Florida operator, DBPR #123613.
You never enter card details on this site: after we confirm your dates, payment runs through a secure Stripe link, and we never see your card number. Free cancellation until 30 days before arrival; full terms.
Pick your dates, see the price
Tap a check-in day, then a check-out day. Booked dates are crossed out. Minimum stay: 7 nights.
Checking live availability. If the calendar does not load, use the request form below or email us your dates; we answer same day.
Prefer email, or have a question before you pick dates? Write to info@happyislandcottage.com and we answer the same day. The same calendar lives on Airbnb and Vrbo; direct bookings carry no platform or service fees, and returning guests do better still. How direct booking works.
Walk through the house
The full tour, floor by floor. Your dates and price are one scroll up whenever you are ready.
The pool is the backyard
Heated pool, paver sun deck, a covered patio with the grill, and the master deck looking over all of it.
Living
The main floor is one open conversation: living room, dining, and the kitchen behind it.
Kitchen and dining
Granite island kitchen with full-size stainless appliances, bar seating for three, and a table that seats eight.
Three bedrooms
King master with its own pool-view deck, a second king bedroom, and a two-bed room the kids will claim.
The baths
Two and a half baths, including a master bath with double vanity and a jetted tub.
The garage that makes friends
Three-car garage where guests before you have left a small treasury of beach toys, loungers, and a beach wagon, all free to use. Golf carts and scooters rent right across the street.
Good to know
- What do guests say about Happy Island Cottage?
- Guests rate Happy Island Cottage 10/10 across 98 Vrbo reviews and 4.93/5 across 75 Airbnb reviews (as of July 2026), with Airbnb check-in and communication both at 5.0. The themes guests mention most are the private pool, the beach, walkability, and family stays. One repeat guest called it "a wonderful house in a wonderful location."
- 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 10:00 AM. Early check-in and late check-out can sometimes be arranged around the cleaning schedule.
Jumps up to the calendar: pick your dates, see the all-in price.