Dragonfly - Southern charm on the North end of Anna Maria Island

Top rated by guests
The large private pool area is THE place to be on a sunny island day!
View of dining area from the kitchen.
Gorgeous evening view! (photo taken prior to turf & putting green installation).
New Exterior Color 2026
Aerial of patio space (Photo taken prior to turf and putting green installation)
review stars
9.9Outstanding
(195 Ratings)
"Our family has stayed at rentals all over the country, the dragonfly was by far the best! The thoughtfulness of the owners is excellent. The house has literally everything for a fantastic beach getawa..."
John K.
Don't miss out! Price and availability may change
9.9 / 10
Outstanding(195 Ratings)

House in Anna Maria Island, FL

8 guests · 5 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in Anna Maria, Florida. Occupancy regulated by the City of Anna Maria is eight persons regardless of age.

Glimpse sparkling turquoise waters from upper floor bedrooms, frolic in the pool with spa and sundeck, and outdoor kitchen, or create culinary delights in the gourmet kitchen with dual-zone wine cooler and Thermador gas range.

Wide open decks with retractable privacy and sun screens plus generously sized rooms enhance guest comfort and offer plenty of space for relaxing moments or celebratory events.

NOTICE:
There is a motion activated video security camera above the garage. The area under surveillance is exposed to the street with no expectation of privacy in this area.

PLEASE NOTE: This property is offered exclusively through VRBO/Home Away and its affiliated entities. Fraudulent bookings through any other service or website are invalid and subject to immediate cancellation without return of deposit.
THIS PROPERTY DOES NOT RENT ON OR THROUGH CRAIGSLIST.

Amenities at Dragonfly - Southern charm on the North end of Anna Maria Island

Non-smoking
No pets allowed

Map of Anna Maria Island, FL

city location on map

Ratings and reviews

9.9 / 10
Outstanding(195 Ratings)
10 / 10Outstanding·Jul 2026
Our family has stayed at rentals all over the country, the dragonfly was by far the best! The thoughtfulness of the owners is excellent. The house has literally everything for a fantastic beach getaway and activities for the kids! 10 out of 10!
10 / 10Outstanding·May 2026
Couldn’t have been a better stay!
10 / 10Outstanding·Feb 2026
Best house we have ever rented. Hosts thought of everything and provided it. We stayed here with our 2 and 4 year old grandkids and there were booster seats, toys, crib options, AND the downstairs play space was a life saver in the coldest week we have ever spent in FLA.
10 / 10Outstanding·Jan 2026
Dragonfly was in excellent condition, maintained spotlessly as usual. We had another memorable time there and appreciate the efforts by Goose and Gander Property Management to make sure we were happy with the house and amenities.

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Dragonfly - Southern charm on the North end of Anna Maria Island. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Dragonfly - Southern charm on the North end of Anna Maria Island pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Dragonfly - Southern charm on the North end of Anna Maria Island?

We found 2 amenities for this rental. This includes non-smoking, and no pets allowed.