Entire home

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

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

A residential area with houses, a swimming pool, and a beach in the background.
A large, multi-story house with a swimming pool, multiple balconies, and a covered patio area.
A two-story house with a balcony, surrounded by palm trees and a swimming pool.
An aerial view of a property with a swimming pool, a covered patio, and a staircase leading to an upper level.
An aerial view of a coastal property with a large house featuring a covered patio with outdoor furniture, a swimming pool, and a well-maintained garden.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Bean Point Beach

Popular amenities

  • Balcony or patio
  • Spa pool on site
  • Private pool
  • Toys
  • Outdoor barbecue
  • Air-conditioning

Explore the area

View map
Anna Maria, FL
  • Place, Bradenton Beach
    ‪1 min walk‬
  • Place, Bean Point Beach
    ‪2 min walk‬
  • Place, Anna Maria Beach
    ‪2 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪43 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Master Suite

1 King Bed

Northeast Bedroom

1 King Bed

Northwest Bedroom

1 Queen Bed

Southeast Bedroom

2 Single Bunk Beds

Southwest Bedroom

1 King Bed

3 bathrooms, 1 half bathroom

Eastern Guest Bath

Bathtub or shower · Toilet

Master Bath

Bathtub · Toilet · Shower only

Powder Room

Toilet

Western Bathroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

Similar properties

Ahhhh. Sunset from the master bedroom deck.
SPOIL YOURSELVES! DIRECT GULF FRONT, PRIVATE POOL, HOT TUB, 5 ENSUITES, SUNSETS!
Anna Maria
  • Ocean view
  • Pool
  • Spa pool
  • Kitchen
10.0 out of 10, Exceptional, (154 reviews)
SPOIL YOURSELVES! DIRECT GULF FRONT, PRIVATE POOL, HOT TUB, 5 ENSUITES, SUNSETS!

About the area

Anna Maria

Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Travelling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and ecotours nearby.
View more Holiday homes in Anna MariaOpens in a new window
Map
Anna Maria, FL

What's nearby

  • Bradenton Beach - 1 min walk - 0.1 km
  • Bean Point Beach - 2 min walk - 0.2 km
  • Anna Maria Beach - 2 min walk - 0.2 km
  • Bayfront Park - 7 min walk - 0.7 km
  • Anna Maria City Pier - 16 min walk - 1.4 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 35 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬3 min drive
  • ‪Anna Maria Island Beach Cafe - ‬10 min drive
  • ‪The Ugly Grouper - ‬8 min drive
  • ‪Ginny's & Jane E's - ‬3 min drive
  • ‪The Waterfront Restaurant - ‬17 min walk

Frequently asked questions

Does Dragonfly - Southern charm on the North end of Anna Maria Island have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Dragonfly - Southern charm on the North end of Anna Maria Island?

As of 3 Nov 2026, prices found for a 1-night stay for 2 adults at Dragonfly - Southern charm on the North end of Anna Maria Island on 10 Jan 2027 start from AU$9,373, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

How much is parking at Dragonfly - Southern charm on the North end of Anna Maria Island?

On-site parking is available at the property.

What time is check-in at Dragonfly - Southern charm on the North end of Anna Maria Island?

Check-in begins at 4:00 PM.

What time is check-out at Dragonfly - Southern charm on the North end of Anna Maria Island?

Checkout is at 10:00 AM.

Where is Dragonfly - Southern charm on the North end of Anna Maria Island located?

This family-friendly Anna Maria holiday home is located by the sea, steps away from Bradenton Beach, Bean Point Beach and Anna Maria Beach. Bay Boulevard Beach and Bayfront Park are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 193 out of 196 reviews
Rating 8 - Good. 2 out of 196 reviews
Rating 6 - Okay. 0 out of 196 reviews
Rating 4 - Poor. 1 out of 196 reviews
Rating 2 - Terrible. 0 out of 196 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house. Really clean. Well stocked. Definitely recommend this place!
Stayed 14 nights in Sep 2026
Response from VrboOwner on 22 Sept 2026
Thank you for taking the time to post a review following your recent day at Dragonfly. Guest recommendations of Dragonfly as a Vacation Rental Property to potential future guests mean a great deal to us. Thank you for that recommendation! We also appreciate you mentioning how beautiful, clean, and well stocked the home is. Hopefully there will be opportunities in the future for you to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing and stocked with everything you might need for the kitchen, bbq, and beach. Everything was super clean. Location was fantastic- right across from the beach. I would return in a heartbeat.
Stayed 6 nights in Aug 2026
Response from VrboOwner on 14 Aug 2026
Thank you for taking the time to post a review following your recent stay at Dragonfly. We appreciate you mentioning how well stocked the home was, as well as its proximity to the beach. The beach at Bean Point and others nearby are truly beautiful. We hope that many wonderful memories were made during your stay and that you will have opportunities in the future to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was my family’s best stay since we started coming to the island a decade ago. The communication and attention to detail is a cut above. Highly recommend this host and this property!
Stayed 7 nights in Jul 2026
Response from VrboOwner on 29 July 2026
Thanks so much for taking the time to post a review following your recent day at Dragonfly. We, and our property management team of Goose & Gander Boutique Property Management and Guest Care , always strive to provide our guests with an amazing vacation experience. We appreciate you having noticed and mentioning the attention to detail at the property. Having previously visited AMI on many occasions, we hope that you will have opportunities in the future to visit both the island and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect property for a large family. Lots of activities and items to enjoy simply at the house. The beach is a stones throw away and the peekaboo views from the home are great as well. The home is well stocked and was very clean.
Stayed 4 nights in Jul 2026
Response from VrboOwner on 29 July 2026
We appreciate your kind words following your recent stay at Dragonfly. It is nice that you found the property to be spacious and with many amenities to enjoy. It is also always nice to hear how clean and well stocked you found the property to be. The proximity to the beach is a highlight for many. Thank you for taking the time to post a review.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Couldn’t have been a better stay!
Stayed 7 nights in Apr 2026
Response from VrboOwner on 5 May 2026
Thank you for posting a review following your recent stay at Dragonfly. We are pleased to hear that you had an enjoyable stay and we hope that you will have opportunities in the future to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 6 nights in Jul 2026
Response from VrboOwner on 15 July 2026
We are thrilled that you enjoyed your recent stay at Dragonfly. We are glad that you found the provided amenities, toys, and activities for adults and children alike, to be plentiful and enjoyable. Thank you for taking the time to post a review and we hope that in the future you will have an opportunity to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Arguably one of the cleanest and best-stocked VRBO's we've ever been in. Comfortable in every room and space. Great layout. Great location near bean point. Super property for families. AC was fantastic. High end kitchen items indoors and out. The pool and hot tub were great. The garage is well stocked with toys and bikes and more. Parking was convenient for our big rental SUV and our golf cart. Communication was simple with the host. We would have a hard time going anywhere else if we return to AMI. This VRBO is a slam dunk if you're looking. It won't disappoint, and we're a bougie traveling family!
Stayed 7 nights in Aug 2026
Response from VrboOwner on 21 Aug 2026
My goodness, what a thorough and thoughtful review! You have touched on so many of the things that we strive to provide for our guests at Dragonfly. Our goal since day one has been to provide our guests with a property that they find clean, both inside and out, well stocked throughout, has plenty of games, toys, bikes, etc., and many other comforts of home. Our hope is that other than a trip to the grocery store or grocery delivery, our guests are able to immediately begin to relax and enjoy all the Dragonfly and AMI have to offer. We are very pleased that you enjoyed your stay and thank you for taking the time to post a review. We hope that you will indeed have opportunities in the future to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 10 nights in Jan 2026
Response from VrboOwner on 16 Feb 2026
We appreciate your glowing and thoughtful review following your recent stay at Dragonfly. It is great to hear that you found everything provided that you needed for your grandchildren. The downstairs area is a great place to enjoy yourselves in the midst of an unusually cool stretch of weather. Thank you for taking the time to post a review and we hope that you will have the opportunity to return to both AMI and Dragonfly again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 10 nights in Dec 2025
Response from VrboOwner on 15 Jan 2026
Thank you for taking the time to post a review following your recent stay at Dragonfly. We appreciate you mentioning the excellent condition of the property, and your overall fondness of the home and the provided amenities. It is very kind of you to mention our Property Management team as well. They are an integral part of Dragonfly’s success as a Vacation Rental Property. We are thankful for you having returned to Dragonfly and look forward to hosting you again in the future.
Verified review

10/10 Excellent

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

Anna Maria stay at the dragonfly

My immediate family stayed at the house and my siblings with their families rented other homes closer to downtown Anna Maria
Stayed 7 nights in Jun 2025
Response from VrboOwner on 8 July 2025
Betty, Thank you for taking the time to post a review following your recent day at Dragonfly. We hope that you and your entire family had a great time and made many wonderful memories. Hopefully there will be opportunities in the future for you to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

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

Fantastic house and location!

Great house, great pool, Bean Point is the best beach in the world!
Stayed 7 nights in Jul 2024
Response from VrboOwner on 31 July 2024
We appreciate your kind words following your recent stay at Dragonfly. The beach at Bean Point is indeed second to none. Thank you so much for taking the time to post a review and we hope that you will have opportunities in the future to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location of this home for beach access and amenities was excellent. Quiet, peaceful and beautiful home. The pool is a plus with children and adds to the entire beach experience. The walk down the block to amazing sunsets with my family are memories we will have.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 1 Sept 2025
We appreciate you mentioning several of the things, from the provided amenities, to the pool, and location of our home, that made your recent stay at Dragonfly so enjoyable. It is always nice to hear our guests mention great memories having been made during their stay. Thank you for taking the time to post a review and we hope that you and your family will have future opportunities to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

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

Family Vacation 2025

Dragonfly is a very well kept property in a very convenient location. Can’t wait to visit again
Stayed 7 nights in Feb 2025
Response from VrboOwner on 28 Feb 2025
Tammi, Thanks so much for the kind comments regarding both Dragonfly and its location. Thank you for taking the time to post a review and we do hope that you will have opportunities to visit both AMI and Dragonfly again in the future.
Verified review

10/10 Excellent

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

Fabulous house and amenities

Our stay was great. The property had everything we needed for a wonderful family vacation and exceeded our expectations. We would certainly stay there again.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 12 July 2024
Nancy, Thank you so much for taking the time to post a review following your recent stay at Dragonfly. It is always nice to hear that our guests had an enjoyable stay and that, in this case, your expectations were exceeded. We hope that you will have opportunities in the future to visit both AMI and Dragonfly again.
Archival

10/10 Excellent

A royal vacation at the Dragonfly.

The Dragonfly thought of everything to make our stay wonderful. A beautiful property made us feel like royalty!!!
Stayed 5 nights in Sep 2017
Response from VrboOwner on 30 Mar 2020
Thank you so much for your kind words, Janet. We endeavored to remodel and furnish Dragonfly in a way that would be welcoming and comfortable for all of our guests, and it's rewarding to know that you feel we achieved such lofty standards. We hope you'll return again and again!
Verified review

10/10 Excellent

Wonderful Vacation Home

This home was beautifully decorated & equipped with everything you need for your stay. It is a short walk to the beach. Our family especially enjoyed the pool & big porch & patio areas.
Stayed 5 nights in Sep 2018
Response from VrboOwner on 30 Mar 2020
Thank you, Leesa, for selecting Dragonfly, and for leaving kind words regarding your recent stay. The primary reason we invested in this property is its location immediately across the street from one of the prettiest beaches in Florida, Bean Point, and we're delighted this decision worked out so well for your family. We hope to see you again in the future!
Verified review

10/10 Excellent

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

Anna Maria July 25

a really excellent find, house in a great location, every toy you need all available.Any problems sorted by a very attentive manager.thoroughly recommended
Stayed 7 nights in Jul 2025
Response from VrboOwner on 6 Aug 2025
We appreciate your kind words regarding Dragonfly’s location and the toys that are provided for our guests to enjoy. It is kind of you to mention our Property Manager. The entire team at Goose & Gander Boutique Property Management and Guest Care are an integral part of Dragonfly being a successful vacation rental property. Thank you taking the time to post a review and we hope that there will be opportunities in the future for you to visit both AMI & Dragonfly again. .
Verified review

10/10 Excellent

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

Dragonfly

We stayed at the Drafonfly for a full week. We couldn’t have been happier with the location, accommodations, cleanliness and presentation of the entire property. The site management Dan & Goose were always available and extremely nice! We highly recommend and will stay again!
Stayed 8 nights in Feb 2025
Response from VrboOwner on 20 Feb 2025
Jenny, We appreciate you taking the time to post a review following your recent stay at Dragonfly. Thank you for mentioning a number of things that made your stay enjoyable, as well as for mentioning our Property Managers, Goose and Dan. They and their team are very instrumental in Dragonfly being a successful vacation rental property. Their attention to detail and ensuring that all guests have a great experience, from the time of their booking, through their departure, is outstanding. We hope that many fond memories were made during your stay and that you will indeed visit both AMI and Dragonfly again in the future.
Verified review

10/10 Excellent

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

Perfect Place

We loved every minute of our stay at Dragonfly. We couldn’t have asked for more comfortable or more beautiful accommodations. It’s our new favorite!
Stayed 7 nights in May 2024
Response from VrboOwner on 20 May 2024
Debbie, Thank you so much for taking the time to post a review following your recent stay at Dragonfly. We are so glad to hear that you enjoyed Dragonfly and the accommodations, and we hope that many wonderful memories were made during your stay. We are pleased that Dragonfly is your new favorite and we hope that you will have opportunities to visit again in the future.
Verified review

10/10 Excellent

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

AWESOME

This place is everything is shows and more, our family enjoyed staying here and will be coming back to this property again!
Stayed 5 nights in Dec 2021
Response from VrboOwner on 16 Jan 2022
Nicholas, thank you for taking the time to post a review regarding your recent stay at Dragonfly. We are thrilled to hear that you and your family enjoyed yourselves and we look forward to hosting you all again in the future.
Verified review

10/10 Excellent

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

Perfect Family & Friends Getaway

This was the perfect hours for our 3 families to come visit AMI. We had adults and kids under 3 and the house set up was perfect. The owners thought of every detail for amenities, we can't wait to visit again!
Stayed 3 nights in Oct 2020
Response from VrboOwner on 10 Oct 2020
Laurel, we are so pleased that you enjoyed your recent stay at Dragonfly. It is also great to hear that you found both the home and provided amenities to be a great fit for you and the rest of your party. Thank you for taking the time to post a review and we certainly hope that you will have an opportunity to visit both AMI and Dragonfly again in the future.
Verified review

10/10 Excellent

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

Love the place, it is.special in so many ways, well equipped with many recreational l alternatives.

Terrific, loved it. Definitely a 5 star fun rental!!
Stayed 7 nights in Nov 2023
Response from VrboOwner on 1 Dec 2023
Wayne, Thank you so much for taking the time to post a review following your recent stay at Dragonfly. We always enjoy and appreciate hearing that Dragonfly is a special place to so many of our guests. We certainly hope that many wonderful memories were made during your stay, and that you will have an opportunity in the future to visit both AMI and Dragonfly again.
Verified review

10/10 Excellent

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

It’s the most amazing rental we’ve ever experienced. It is definitely our home away from home.

It’s always the best vacation EVER! See you next June!!!
Stayed 8 nights in Jul 2021
Response from VrboOwner on 11 Aug 2021
Tammie, it is so nice to hear Dragonfly and AMI referred to as both the “best vacation ever” and “your home away from home”. It sounds as if you had a wonderful time and we are so pleased that you will be visiting again next June. Thank you for taking the time to post a review.
Verified review

10/10 Excellent

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

Excellent Property

Anyone with small children to adults will love this property. The proximity to the beach was perfect. The rental company was amazing! We had such a good time, we have already booked for next year!
Stayed 7 nights in Jul 2022
Response from VrboOwner on 12 Aug 2022
Lynn, We are very pleased that you found Dragonfly to be a great fit for all ages, as well as mentioning its close proximity to the beach at Bean Point. We hear from many guests about their pleasure in dealing with our property management team of Goose & Gander Boutique Property Management. They take the extra steps to ensure that all of our guests needs are met from the time the property is booked and throughout their stay. Thank you for taking the time to post a review and we look forward to hosting you again next year.
Verified review

10/10 Excellent

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

absolutely the perfect beach house!

This is, by far, the best beach house we have ever rented. It is perfect in every way. A fabulous property - so very clean and comfortable. Every luxury your family needs for a perfect vacation.
Stayed 5 nights in Jan 2021
Response from VrboOwner on 14 Jan 2021
John, we appreciate your kind words regarding your recent stay at Dragonfly. We strive to provide our guests with a clean property, both inside and out, and to have plenty to choose from in terms of “things to do”. It is great to hear that your expectations were met. Thank you for taking the time to post a review and we certainly hope that in the future you will have more opportunities to visit both AMI and Dragonfly.
Tell us how we can improve our siteShare feedback