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Happy Island Cottage: Heated Pool, 5-Min Walk to Beach, Pet Friendly

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A two-story house with a balcony, a swimming pool, and outdoor furniture.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a built-in oven.
A two-story house with a balcony, a garage, and a circular emblem on the facade.
A bedroom with a white bed, a nightstand, a lamp, and a view of a balcony with outdoor plants.
A modern kitchen with a stainless steel refrigerator, a built-in oven, a microwave, a granite countertop, a sink, and three red bar stools.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 62000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Holmes Beach, FL
  • Place, Island Gallery West
    ‪6 min walk‬
  • Place, Bradenton Beach
    ‪6 min walk‬
  • Place, Holmes Beach Beaches
    ‪16 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪36 min drive‬

Room options

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About the neighborhood

Holmes Beach

With a stay at this vacation home, you'll be centrally located in Holmes Beach, within a 5-minute drive of Manatee Public Beach and Bradenton Beach. .This family-friendly vacation home is 2.6 mi (4.2 km) from Bean Point Beach and 4.9 mi (7.9 km) from Coquina Beach.
View more Vacation Homes in Holmes BeachOpens in a new window

What's nearby

  • Island Gallery West - 6 min walk - 0.4 miles
  • Bradenton Beach - 6 min walk - 0.4 miles
  • Holmes Beach Beaches - 16 min walk - 0.9 miles
  • Manatee Public Beach - 19 min walk - 1.0 mile
  • West Coast Surf Shop - 3 min drive - 1.3 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 38 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬18 min walk
  • ‪The Sandbar Restaurant - ‬6 min drive
  • ‪The Ugly Grouper - ‬2 min walk
  • ‪Ginny's & Jane E's - ‬5 min drive
  • ‪Skinny's Place - ‬3 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Happy Island Cottage: Heated Pool, 5-Min Walk to Beach, Pet Friendly

Your own heated pool, a five-minute walk to the Gulf, and the whole house to yourselves in quiet Holmes Beach on Anna Maria Island. 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.

The home is a modern 2,000 sq ft beach house that sleeps 6: two king rooms, a twin room, a queen sleeper sofa, and 2.5 baths with a jet tub. A private, fenced pool with safety alarms, two decks, a grill, a full kitchen, Electrolux washer and dryer, fast 173 Mbps wifi, a 3-car garage and EV charger, and easy self check-in. Two dogs welcome, any size, and the garage is stocked with beach toys, loungers and a wagon to borrow.

Leave the car parked: it is a five-minute walk to a wide Gulf beach, and steps to the marina, shops, groceries and the Ugly Grouper. The free island trolley stops 100 steps away.

Want to be right on the sand, or planning a simpler getaway? Look up Happy Turtle, our two cute cottages 60 steps from the beach, 10 minutes away in Bradenton Beach.

* AC holds the 72-80F range. The Nest is not locked: if it reads 76, that is Eco mode after the house sat empty, and it resumes your setting on its own.
* Pool Heater is optional - please contact us for details prior to your arrival.
* TVs are streaming through Amazon Fire Sticks. You are free to use any of your subscription services, but please remember to log out after your vacation. If you are not familiar with Amazon Fire Sticks or smart TVs in general, please search online for instructions. We do not provide assistance with basic operations.
_______________________________
Legal Mumbo Jumbo:
(VRC) License Number: DWE5106980
Minimum stay requirements: weekly
Number of on-site parking spaces: 4
Noise ordinance information: Holmes Beach, FL has a noise ordinance limiting sound to 65 dBA from 7 a.m. to 10 p.m. and 50 dBA from 10 p.m. to 7 a.m.
Our prices include all fees. No hidden fees.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment. The bathroom has a jetted bathtub and a hair dryer.
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.
Guests will find features like internet access, onsite parking, and a car charging station.

Property amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Car not required
  • Limited onsite parking (max 3 spaces)
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Jetted bathtub
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • DVD player
  • Games
  • Music library
  • Smart TV
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 pets total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Safe

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the marina
  • Near the sea

Things to do

  • Boat
  • Heated pool
  • Optional golf privileges
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Electric car charging station
  • Garden
  • Unit size: 2,000 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
Return any furniture to its original place.
Clean up grill - if used.
Failure to complete these may result in a negative review from the host.

Rules

AC is set to range 72F - 80F. No exeptions pls.
No parties allowed, We are family vacation house in a residential neighborhood.
No extra visitors allowed in the house, without prior agreement.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
2 total pets
Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is not required for transportation to and from this property

Property is also known as

Happy Island Cottage Heated House Holmes Beach
Happy Island Cottage Heated House
Happy Island Cottage Heated Holmes Beach
Happy Island Cottage Heated
Happy Island Cottage With Heated Private Pool

Happy Island Cottage: Heated Pool, 5-Min Walk to Beach, Pet Friendly Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 91 out of 98 reviews
Rating 8 - Good. 5 out of 98 reviews
Rating 6 - Okay. 2 out of 98 reviews
Rating 4 - Poor. 0 out of 98 reviews
Rating 2 - Terrible. 0 out of 98 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Alexandra v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was great, host was extremely responsive when we had questions, definitely recommend!
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Juliet V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our second year staying at this property, and we absolutely love it !!

Perfect location
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Nicola A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Relaxation

Just returned from a wonderful stay! Would recommend this house to anyone who wants a relaxing, refreshing break.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Victoria E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location!

We had a wonderful time during our stay. We loved the swimming pool and how close the house was to the beach and restaurants/coffee shops. Rooms are spacious and the owner was wonderful. We will be back!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Getaway

Great location. Short walk to the beach and many restaurants.
Stayed 7 nights in Jan 2024
Verified

10/10 Excellent

Erin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place! Book it!

We had a fabulous stay at this property. The perfect amount of space for our family with very comfy beds, lots of seating, and just a comfortable feel. A 4 minute walk to the beach, it can't get any better!
Stayed 7 nights in Jan 2023
Verified

10/10 Excellent

Joel W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome time

We had the best vacation we’ve ever had!
Stayed 13 nights in Jun 2023
Verified

10/10 Excellent

Rebecca H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great girls getaway

We stayed here for a few nights for a girls Anna Maria Island getaway with grandma, daughters and two granddaughters. We had a great time, the pool is wonderful, short walk to the beach, the place was clean and the owner was very helpful! We would definitely come back!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Anne G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice

Well maintained, good location!
Stayed 7 nights in Feb 2024
Verified

10/10 Excellent

Mary M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMI Vacation 2024

Beautiful home! Everything is very clean and well maintained. Amazing vacation for our first time at AMI
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Mark R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMI House with pool

The house and pool were very well kept. The area was convenient, close to the beach and shopping. I would recommend this property. A great family location.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Peggy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

March 2026

Alex met us at the house at check in, gave us an excellent recommendation for a restaurant (we went there twice), and was very responsive when we needed help with anything. We enjoyed our stay a lot!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Jenny M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience

Our family enjoyed our stay at Happy Island. The house was clean, and the layout worked well for our family. The pool area is very nice. The location made it easy to access all the island has to offer. Alex is a very kind and helpful host. Would love to stay here again.
Stayed 7 nights in Feb 2020
Verified

10/10 Excellent

Madeleine S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Anna Maria

Always enjoy our stay on Annamaria Island. Property was very nice with a private garden and pool. Alex was responsive and easy to get pucked in touch with.
Stayed 14 nights in Feb 2024
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beach vacay!

This home was perfect for our family! Beach, restaurants, ice cream, sunrise, fresh seafood store, boat docks for excursions all walkable. Grocery store close too. Air conditioning worked great! The pool was perfect for cooling off. The kind owner checked on us and communicated rapidly. The home was very clean! We loved it and would definitely stay there again!
Stayed 10 nights in Jun 2025
Verified

10/10 Excellent

Adam O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location!

The house was a short walk to the beach, and was close to everything you needed. Lots of restaurants and bars within walking distance. We really liked being so close to the north end of the island. The house was pretty much exactly as described, and the kids loved the playing in the pool every day after coming back from the beach.
Stayed 6 nights in Jan 2023
Verified

10/10 Excellent

Jeannie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mother's Day

We had a wonderful time. The pool was great, the location wonderful! Definitely get a golf cart to get around, it so much easier and can enjoy the island better. Definitely will be back!
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Barbara Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMI Heaven

The house was perfect for our family, our host was super and really made us feel welcome and ensured we had everything we needed. The pool and pool area were spotless and relaxing and the beach was a really short walk away, best of both worlds. We’d return for sure😎
Stayed 8 nights in Apr 2024
Verified

10/10 Excellent

Donald S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

island

Everything went great
Stayed 11 nights in Dec 2022
Verified

6/10 Okay

Kim D.

Liked: Communication
Disliked: Location

Vacay 2025

This is our 4th time in AMI.. we have stayed at different properties, all have had different things to offer. This one was ok except we did not realize that we are on top of The Ugly Grouper. Trucks unloading almost every morning to deliver supplies to the restaurant. The pool was nice.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Tina C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family getaway

We had a great time on Anna Maria Island! The house was in a great location - a few blocks to the beach and close to restaurants and shopping. The pool area is beautiful and was the perfect size for our family of 5. The house is clean and had most everything we needed. It was so nice to have beach equipment (chairs, wagon, etc) there for us so we didn’t have to bring it. The owner came to check in with us and make sure the pool was clean. We would definitely recommend this house for a nice family getaway!
Stayed 6 nights in Jun 2023
Verified

8/10 Good

John N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy Island Cottage

The home was very adequate and was found as advertised. Not having any toilet paper or paper towels was annoying, additionally I would have paid more to have access to the thermostat of the pool, set at 85 degrees and locked made the northern facing pool unusable. Owner was pleasant.
Stayed 6 nights in Jan 2021
Verified

10/10 Excellent

Janet W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best vacation ever!

This was a wonderful place to stay. Clean and is supplied with everything you need. Alex will help out with any questions you need answered. Everything is in walking distance. Pool was the best! Every restaurant in Holmes Beach gets a five star. Rented a golf cart and toured Anna Maria and went to both piers to eat. Will be back next year. Thank you Alex for everything. The Woodwards
Stayed 14 nights in Feb 2023
Verified

10/10 Excellent

Pam O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The BFF Fifty and Fabulous Tour

Fabulous place to stay. Centrally located. A stroll to the beach. The house had more than enough room for everyone and three bathrooms. The pool is spectacular and while having cocktails the Ugly Grouper next door plays music. There is a place to sit out od the sun. I highly recommend renting a golf cart. We rented from the Toy Barn. We all said we would be back and rent the exact house if we can. I also suggest experiencing some drinks at the doctors office.
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Alan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent pool deck and location

Check in was a breeze. Communication with the host was excellent. Unless weather prevents it, Wednesday is always pool maintenance day and Alex always communicated before stopping over. Easy three block walk to beach access. There is no parking at this beach access which is a plus because there were less people. Ugly Grooper and shops are easy walking distance. If you bring a dog, the dog park is approximately three blocks away also. With the tiki bar Ugly Grooper so close their dumpster is right next door. Just be prepared for it to be dumped on a regular basis between 630-700am. Loud. By far our favorite part of this property was the pool deck.
Stayed 28 nights in May 2024

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