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Dream

of the perfect vacation

and let Once Upon a Beach make it come true...

Write the Next Chapter of your Vacation Story...

A world-class Anna Maria island getaway commands a premier vacation rental experience. Immerse yourself in laid back luxury in one of our pristine Anna Maria Island vacation rental homes with a local team dedicated to providing exceptional guest experiences from booking through departure. Whether you are looking for an intimate escape for two in one of our beach chic cottages, searching for a luxury Anna Maria Island rental with a private pool or bringing the entire extended family to stay in one of our large family friendly Anna Maria Island rentals, rest assured you will arrive to discover a meticulously cared for home with unique thoughtful amenities, carefully crafted concierge style island information, and always find yourself just steps to the pristine sugary sand beaches and gin clear waters of our island paradise.

As a boutique luxury vacation rental and property management company in Anna Maria Island, FL, Once Upon A Beach prides ourselves on providing an intimate island experience with five-star care and attention to detail in one of the most beautifully quaint beach towns on earth… the place we lovingly call home, Anna Maria Island. Write the next chapter of your vacation story with us and make memories that will last a lifetime.

From cottages to luxury homes

Book Your Stay With Us

Featured Property Tern Key

Anna Maria | from $560 per night

Tern Key

4 bedrooms |

4 baths |

8 guests

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Featured Property Sea La Vie Beach House

Anna Maria | from $540 per night

Sea La Vie Beach House

4 bedrooms |

4 baths |

8 guests

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Featured Property Serenity Now

Holmes Beach | from $380 per night

Serenity Now

4 bedrooms |

3 baths |

8 guests

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Featured Property Shore's Nice

Anna Maria | from $265 per night

Shore's Nice

2 bedrooms |

2 baths |

4 guests

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Featured Property A Shore Thing

Anna Maria | from $600 per night

A Shore Thing

4 bedrooms |

5 baths |

10 guests

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Featured Property Mango Bay

Holmes Beach | from $360 per night

Mango Bay

4 bedrooms |

3 baths |

8 guests

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Featured Property Anna Maria Aloha

Anna Maria | from $250 per night

Anna Maria Aloha

3 bedrooms |

2 baths |

6 guests

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Featured Property Three Little Birds

Anna Maria | from $620 per night

Three Little Birds

4 bedrooms |

3 baths |

8 guests

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Featured Property Catching Waves

Holmes Beach | from $220 per night

Catching Waves

2 bedrooms |

2 baths |

6 guests

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Featured Property Mariner's Crossing

Bradenton Beach | from $765 per night

Mariner's Crossing

8 bedrooms |

7 baths |

18 guests

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Perfect family gateway
This home beautiful beach home. It was just perfect. Fully equipped with everything that you need. We had an amazing family getaway. Close to everything. Beach is just 1 block away. The staff at once upon a beach are amazing and very responsive. We will be back.

Paola

Slice of Paradise
What an awesome vacation! This was our first trip to Anna Maria, but I instantly deemed it “my heaven”! The house was just perfect- clean as can be, comfortable, great location! The only negative was we actually had to leave paradise! :) We highly recommend staying here!!

Kathy

BEST HOUSE IN ANNA MARIA!
This is hands down the best home for staying in Anna Maria. The home is a perfect layout, all of your amenities, pool, spa, and best of all privacy!! Each room has its own private bathroom and provides adequate space. Only steps away from the beach. Everything was clean, well put together, and an overall extremely comfortable stay. The plants provide an extremely relaxing scenery that you will not find at any other home. If you are looking to stay in Anna Maria, I would strongly suggest staying at this property! 11/10 recommended.

Anonymous

This was our first time coming to AMI, and we could not have chosen a more perfect location to spend it. The cottage was just the right size for our family of 4 (our boys are 5 and 7). It was well-appointed, decorated beautifully, and had everything we needed for the week. We also rented a golf cart from Once Upon A Beach and would definitely recommend it! We went to Bean Point and the access at White Avenue most days, and the golf cart made the trip much more manageable! We had a tiny issue the first night upon arrival, but a quick text to Mike and it was resolved within 10 minutes. We will definitely book again!

Jeanne

Paradise!
This was our first visit to AMI, and it was better than we ever imagined! The beaches are gorgeous, the sunsets amazing! The house was perfect…a very quick walk to the beach, meticulous and so comfortable. They thought of every last detail. Working with the folks from Onceuponabeachami has been a pleasure from start to finish. I highly recommend!! This place is a little slice of heaven.

Anonymous

We have been renting this home for the past 10 years and were fortunate enough to rent it again for almost 2 weeks in May 2021. The property is fabulous! The home was very clean and the privacy of the pool area can’t be beat. The home is so convenient to everything on the Island. The rental agency was great to work with and very responsive. Thanks to Nikki, Mike & Brittany for a memorable vacation. Can’t wait to stay here again! 5 stars for this property & the agency!

Sherry

For starters, I’m extremely impressed with the level of care and service Mike and Nikki provided us during our stay. As we were checking in, Nikki stopped by to ensure the house was ready for our arrival and that we were happy with the condition of the home. A few days into our visit, we had a small issue that Mike resolved within a few minutes of contacting him. He followed up with us the next day to let us know about the long term fix so that other guests would not encounter the issue going forward. As for the home, it was perfect for our family of four. While we didn’t spend much time inside, the beds were comfortable and there was plenty of space for us to relax and stretch out. The backyard pool area has a tropical feel with plenty of furniture around the pool and a cool bar area with a TV. Our girls loved swimming while my wife and I enjoyed the hot tub. The best beach on Anna Maria is a 3-4 minute walk from the house. It wasn’t too crowded even during the busiest week of spring break. Nice touch having beach gear (wagon, chairs, umbrella, towels) available for guests to use. When we come back to the island, we will be booking again with Mike and Nikki – hopefully it is sooner rather than later!

Matt

We have been staying in VRBO properties for 15 years. Seaswept Mermaid is in our top THREE. The house is immaculate, has all the amenities you need for adults and kids, steps away from a beach, a short walk or golf cart ride to food and shopping, and the pool/hot tub/decks are just what you need in a Florida home. We were two families in this house and never felt crowded. You can sit on the front deck and watch the sunrise, or watch the afternoon/evening thunderstorms. You can sit on the back deck and enjoy the peace and quiet. You can easily paddle board or kayak on the ocean or canal. The amenities that they provide including ample cooking utensils, pots, pans, dishes, beach/pool towels are by far the best of any VRBO we have stayed in. The communication from Once upon a beach from booking to departure was top notch. HIGHLY recommend checking out this property. You will love it.

Candice

This is my third time staying at one of the Once Upon a Beach homes. This is my favorite house so far. It was perfect for bringing my 3 kids and mother-in-law with this time. Everyone had their own bedroom and plenty of space. The master bedroom on the main floor was awesome. I really liked the huge walk-in closet and the double sinks meant my husband had his own. We cooked at the house a few times and had everything we needed. The grill could be replaced as it’s a little rusty, but we made it work for us. The kids enjoyed the pool everyday. There are games and puzzles in the bunk room that the kids liked. The garage has quite a few beach supplies. The bigger camping chairs were nice for my mother-in-law to sit in. The house is super close to restaurants and gift shops. We enjoyed being able to walk to to places instead of having to drive. Nikki and Mike are really great to work with and they take exceptional care of all their properties. All 3 houses I have stayed at have been super clean. They are only a text or phone call away if you ever need anything. I can’t wait to come back in October.

Crystal

This boutique vacation rental company is the BEST on Anna Maria Island . Each of their rentals are beautifully decorated, ideally located and full of amenities ! If you’re visiting here .. you should call them! I did .. and I never wanted to leave

Kim

We loved our stay! The pool is so nice and the home is in a convenient location. The walk to the beach was easy even with two young children. Our favorite spot was the upstairs balcony where we watched the sunset a few nights. Thanks for having us and making the process so easy from booking to check out. We come to AMI every year and would definitely stay with Once Upon a Beach again!

Heather

We just returned from a week stay at Sol Mate and would have stayed longer if we had the chance. We truly enjoyed the screened in porches, perfect for dining without concern for mosquitos and for relaxing at the end of the day- you can even peep a small slice of the gulf from the upper porch which was an added bonus! The beds/linens were very comfortable, the house was clean and the beautifully landscaped pool area with spa and bar/tv was perfect for our family. It is always so nice to have a beach cart, beach umbrellas and chairs available to use, thank you for providing these things! We visit AMI 2x/year and are already looking forward to a return visit to Sol Mate! Thank you to Brittany for helping us with an item we left behind- we really appreciate the amazing customer service!

Krista

We have stayed in many different homes in AMI and Coconut Lagoon was by far the best. The backyard oasis was fabulous and spent 95% of our time enjoying the pristine landscape and pool. Beach access, shopping and dining were within walking distance only our golf cart was our preferred transportation. Can’t wait to book another memorable family vacation with Once Upon A Beach. Great time thanks to you and your wonderful staff. 5 star for sure

Jill Choate

Our family of 6 had a wonderful stay at Sea Life Happy. The house is beautifully decorated and very well appointed. Our favorite feature of the house was the open floor plan on the main level. We had friends at a neighboring house and Sea Life Happy was the perfect gathering spot for large dinners and game time. There was plenty of space for serving and seating for 15 during meals. The outside pool/ cabana/dock area was also wonderful for relaxing and entertaining. I would recommend a golf cart with this property. We used our golf cart for trips to the beach, supply runs to the store and joy riding. We would certainly recommend Sea Life Happy and would love to stay there in the future. We had a very positive experience with Once Upon A Beach and will certainly contact them for our next stay on AMI. Communication was wonderful and everything was just as stated. Great experience all around!

A. Blackston

The home was as described and the Once Upon A Beach was always responsive and available. Wouldn’t hesitate to book thru them again!

Cindy

We just got back to Boston after a week a Sea La Vie. There are not enough words to describe the home and its amenities. To say we were spoiled by our stay is an understatement! I can also say that if we had an issue or concern it was handled immediately, no question asked. we WILL be booking again next year through Once Upon A Beach!!!!

Stephanie

This boutique vacation rental company is the BEST on Anna Maria Island. Each of their rentals are beautifully decorated, ideally located and full of amenities ! If you're visiting here .. you should call them! I did..and I never wanted to leave...

Jill Choate

About Anna Maria Island

Explore Our Paradise

Your vacation rental experience doesn't end with opening the front doorâ€¦ our local team lives and plays here every day. We have the knowledge and insight on how to make the most of your island vacation from restaurant and fishing charter recommendations, family friendly activities, beach and weather tips, equipment rentals and private services like transportation, grocery delivery, or private chefs.

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Property Management

With our exclusive limited portfolio you are not just another property and owner to us. We become a partner with you in the care of your home and all its guests. We work tirelessly to make vacation rental ownership as stress free to you as possible. We set the bar with the highest levels of standards of care, clear and concise communications and goals for your home, and our top of the line revenue optimization, management, and marketing strategies.

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