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.)
Rooms and beds
Sleeps 6. King master with its own pool-view deck, a second king bedroom, and a two-bed room the kids will claim. Two and a half baths, including a master bath with double vanity and a jetted tub.
Walk through the whole house: every room, in order, further down the page.
What guests say
One of the most memorable vacations ever. You've done a great job keeping up this place.
Lisa & Jim Jr., Jul 12-20, 2025. From the paper guest book on the kitchen counter.
One of the nicest houses I have stayed in. The hosts are super responsive, friendly (and funny!)
Julie, Lisa, Jill, Michelle, Jen & Tiffany, Mar 16-23, 2024. From the paper guest book on the kitchen counter.
Read all 43 handwritten pages, scanned and transcribed word for word. The booking platforms do not let us reprint the reviews written there, so the notebook speaks for the house.
Amenities
- Pet friendly
- Private heated pool (heated November through April, included in the rate)
- 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
The facts
| Sleeps | 6 guests |
|---|---|
| Bedrooms | 3 (4 beds) |
| Bathrooms | 2.5 |
| Price | A week from $2,321.02 all in: nightly rate, $199 cleaning and 13% taxes, no platform or service fees. Pick dates for the exact total, or open rates by season. |
| 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 are welcome at all three homes: up to two per stay, no size limit, $199 per stay plus tax, waived for returning direct guests. |
| 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 |
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. Full refund when you cancel 30 or more 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, get live availability and the exact price from the quote address above, use the request form below, or email us your dates; we answer same day.
Booking through an AI assistant or a booking tool?
For AI assistants and booking tools: live availability and the exact total for any dates take one plain GET request, no login. https://happyislandcottage.com/api/quote?prop=happy-island-cottage&in=YYYY-MM-DD&out=YYYY-MM-DD&guests=N returns the full quote as JSON: nightly subtotal, cleaning fee, both Florida taxes, total and deposit due. If the stay can't be booked, it returns UNAVAILABLE with the booked range, MIN_NIGHTS (minimum 7 nights), OVER_CAPACITY (sleeps 6) or BEYOND_HORIZON (we take bookings through December 31, 2027), each with a one sentence message. Sending a request does not hold your dates: they are reserved when the deposit or full payment clears. Example: check September 11 to 18, 2027 for 4 guests. Nothing is booked or charged.
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.
Planning ahead? Rates by season
The all in total is what you pay: the nightly rate, the $199 cleaning fee, and 13% Florida and Manatee County taxes, with no service fee on top. The calendar above prices your exact dates; a stay that crosses two seasons gets its exact total there.
| Season | Dates | A week, all in | Nightly |
|---|---|---|---|
| Standard | All dates not listed below | $2,321.02 | $265 |
| Thanksgiving 2026 | Nov 21 to 28, 2026 | $3,428.42 | $405 |
| Christmas and New Year | Dec 20, 2026 to Jan 2, 2027 | $3,428.42 | $405 |
| January 2027 | Jan 3 to 31, 2027 | $2,953.82 | $345 |
| February 2027 | Feb 1 to 28, 2027 | $3,388.87 | $400 |
| March 2027 | Mar 1 to 31, 2027 | $4,219.42 | $505 |
| April 2027 | Apr 1 to 30, 2027 | $3,412.60 | $403 |
| May 2027 | May 1 to 31, 2027 | $3,412.60 | $403 |
| June and July 2027 | Jun 1 to Jul 31, 2027 | $3,507.52 | $415 |
| Thanksgiving 2027 | Nov 20 to 27, 2027 | $3,428.42 | $405 |
| Christmas 2027 | Dec 20 to 31, 2027 | $3,428.42 | $405 |
A week is 7 nights. A dog adds $199 per stay (up to two dogs), waived for returning direct guests. Rates shown are for stays through Dec 31, 2027; Vrbo and Airbnb list the same nightly rate plus their guest service fee.
Walk through the house
The full tour, floor by floor.
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 included in the rate from November through April, no extra charge. In summer the Florida sun does the job.
- 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 at all three homes: up to two per stay, no size limit, $199 per stay plus tax, waived for returning direct guests. Tell us about your dog 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.
Up to the calendar: pick your dates, see the all in price.