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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

The large private pool area is THE place to be on a sunny day!
Gorgeous evening view! (photo taken prior to turf & putting green installation).
Cornhole game spotted from above!
Aerial of patio space (Photo taken prior to turf and putting green installation)
The pool area is a great place to relax after sunset.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms3+ bathroomsSleeps 8

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer

Explore the area

View in a 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.)
    ‪35 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 Twin 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

About this property

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

Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in Anna Maria, Florida.

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
Well-behaved children are always welcome
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items and take out the trash
Turn off the lights and lock the doors
HONOR THE 10AM CHECK OUT TIME The housekeeping staff arrives at 10am to prepare the house for the next guests. ON DEMAND SERVICES Make sure you have logged out of all apps on the TVs (if applicable).
GARBAGE & LEFTOVER FOOD: You may leave unused food/drinks in the kitchen. Please discard all restaurant leftovers. LINENS: It is not necessary to strip the sheets from the beds or wash towels.
RETURN ITEMS TO THEIR PLACE: Return all furniture and décor that was moved during your stay to its original locations, including outdoor furniture. This is a private home. Thank you for your respect!
Failure to complete these may result in a negative review from the host.
The signed Rental Agreement ("RA") must be returned to Manager within 7 days of receipt. Rental is subject to cancellation until the RA is received.
In the event the language in the Rental Agreement ("RA") conflicts with the language found on this website, the language of the RA shall control
Violation of Occupancy or Noise restrictions by city ordinance and the Dragonfly RA shall be considered a default subject to eviction without refund

Important information

You need to know

Property # 961328
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

About the neighborhood

Anna Maria

Located in Anna Maria, this vacation home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Traveling 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/biking trails and cycling nearby.
View more Vacation 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-Bradenton Intl. Airport (SRQ) - 35 min drive

Restaurants

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

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 May 10, 2026, prices found for a 1-night stay for 2 adults at Dragonfly - Southern charm on the North end of Anna Maria Island on Aug 26, 2026 start from $1,146, 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?

Onsite 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?

Check-out is at 10:00 AM.

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

This family-friendly Anna Maria vacation home is located by the sea, steps from Bradenton Beach, Bean Point Beach, and Anna Maria Beach. Palmetto Avenue Beach and Bayfront Park are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 187 out of 190 reviews
Rating 8 - Good. 2 out of 190 reviews
Rating 6 - Okay. 0 out of 190 reviews
Rating 4 - Poor. 1 out of 190 reviews
Rating 2 - Terrible. 0 out of 190 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Joseph B.

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 May 5, 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

10/10 Excellent

Carol B.

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 Feb 16, 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

10/10 Excellent

steve c.

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 Jan 15, 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

10/10 Excellent

elena g.

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 Sep 1, 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

10/10 Excellent

betty Q.

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 Jul 8, 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

10/10 Excellent

Nick Rowe

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 Aug 6, 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

10/10 Excellent

Tammi H.

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 Feb 28, 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

10/10 Excellent

Verified traveler

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

Incredible Home!

This is our second time back to the Dragonfly! It simply can’t be beat. They provide everything you need to enjoy the pool and beach. Tons of chairs, towels, toys, etc. We have never been to a rental that is so well stocked and so well taken care of. The home is beautiful and the location is perfect. We will be back!
Stayed 7 nights in Jun 2025
Response from VrboOwner on Jul 23, 2025
We appreciate you mentioning how well the home is stocked and the convenient location. Our wish is that our guests do not have to pack many of the things needed for a great beach vacation and, besides a trip to the grocery store, that they can begin to enjoy themselves immediately upon arrival.
Verified

10/10 Excellent

gt a.

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 Jul 31, 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

10/10 Excellent

Nancy C.

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 Jul 12, 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.
Verified

10/10 Excellent

Jenny P.

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 Feb 20, 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

10/10 Excellent

Susan L.

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

Perfection

This is our 7th year renting Dragonfly for three weeks and we’ll be back till we die. It is fabulous. I cannot recommend this property enough.
Stayed 22 nights in Mar 2025
Response from VrboOwner on Apr 16, 2025
Sue, We are incredibly grateful for your continued patronage to Dragonfly. We hope that you and your family had an amazing stay with lots of wonderful memories made. Thank you for taking the time to post a review and we look forward to you returning next year. Take care!
Archival

10/10 Excellent

Janet G.

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 Mar 30, 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

10/10 Excellent

Debbie K.

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 May 20, 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

10/10 Excellent

Leesa R.

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 Mar 30, 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

10/10 Excellent

Wayne C.

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 Dec 1, 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

10/10 Excellent

Nicholas W.

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 Jan 16, 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

10/10 Excellent

Laurel W.

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 Oct 10, 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

10/10 Excellent

TAMMIE R.

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 Aug 11, 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

10/10 Excellent

Lynn G.

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 Aug 12, 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

10/10 Excellent

John N.

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 Jan 14, 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.
Verified

10/10 Excellent

Stephanie H.

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

Wonderful as always

This is our third visit to the property. The layout, amenities and proximity to the beach are perfect for a large family. We will be staying again next year.
Stayed 7 nights in Nov 2019
Response from VrboOwner on May 13, 2020
Stephanie, we are pleased that you found Dragonfly to be the perfect home for you and your family, and we look forward to you visiting again next year. Thank you for taking the time to post a review.
Verified

10/10 Excellent

Laura W.

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

Amazing property - everything you need!

We loved staying at Dragonfly. The property has everything you could possibly need, both inside and out. We loved the pool, hot tub, and being a short walk from the beach. The new putting green was fun for all ages. We can't wait to visit again!
Stayed 7 nights in Dec 2022
Response from VrboOwner on Dec 14, 2022
Laura, Thank you for having taken the time to post a review following your recent stay at Dragonfly. We strive to provide our guests with an abundance of things to do during their stay. Thus, they can choose to be as active as they wish to be, or simply relax. Thank you for referencing a few of the things that you enjoyed during your stay. Hopefully there will indeed be opportunities in the future for you to visit both AMI and Dragonfly again.
Verified

10/10 Excellent

Gretchen N.

Beautiful house, comfortable bedrooms, awesome pool and decks, exceptional kitchen

The special amenities-bikes, chairs, umbrellas, floats and sand toys and sand wagon were especially appreciated.
Stayed 7 nights in Jun 2018
Response from VrboOwner on Mar 30, 2020
Thank you, Gretchen, for your kind words about Dragonfly. We love this home, and are honored that you enjoyed it so much you're returning next year. Rest assured, our entire team will work hard to make your next Anna Maria vacation even better than the first!
Verified

10/10 Excellent

Susan L.

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

Heaven

We have been renting this property for six years now and I’ve already booked it for 2025. The hosts are like family, the property is spectacular and the property managers are perfect.
Stayed 16 nights in Mar 2024
Response from VrboOwner on Apr 10, 2024
Sue, Thank you so much for taking the time to post a review following your recent stay at Dragonfly. Your comments warm our hearts and are much appreciated. We always look forward to you and your family visiting and hope that you have made many lifelong memories along the way. Take care and be well!

About the host

Hosted by Dan & Goose Pekarek of Goose & Gander Boutique Property Management & Guest Care

Host profile image

Why they chose this property

This home was built in an extraordinary location: across North Shore Drive from one of the most famous beaches in Florida - Bean Point. Rooms are large and comfortable, and the property offers privacy as well as plenty of room to play. Extensive renovations have created a delightful environment to experience all of the best aspects of the Florida beach lifestyle.

What makes this property unique

A coveted location on North Shore Drive across from Bean Point is the key attraction of this property. A new swimming pool with sundeck and spa, a Thermador gourmet kitchen, and an oversized deck and covered patio are additional assets that make Dragonfly an exceptional venue for family gatherings, weddings, and the creation of priceless memories.

Languages:

English

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