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

Family-friendly holiday home in Anna Maria with a hot tub

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

Fridge, microwave, oven, stovetop
Exterior
Beach nearby, sun-loungers, beach towels
Fridge, microwave, oven, stovetop
Smart TV, fireplace, DVD player, ping pong
Located across from famous Bean Point Beach, Dragonfly is a tranquil retreat with glimpses of sparkling turquoise waters from upper floor bedrooms. Unwind in the pool with spa and sundeck or enjoy al fresco dining in the outdoor kitchen.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 8268 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace

Add dates for prices

About this property

Entire place

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

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.
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.

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Golf
  • Heated pool
  • Kayak
  • Table tennis
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing 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

  • Bicycles
  • Garden
  • Housekeeping (on request)
  • Unit size: 2,884 square feet

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  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, Exceptional, 235 reviews
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items and take out the rubbish
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.

Rules

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

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Well-behaved children are always 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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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 recommended for transport to and from this property

Property is also known as

Dragonfly ern Charm Anna ia's
Dragonfly Southern Charm on Anna Maria's Famous North Shore
Discounts April MAY Rates Reduced!
Dragonfly Southern Charm on Anna Maria's Famous North Shore

About the area

Map
Anna Maria, FL

What's nearby

  • Anna Maria Beach - 2 min walk - 0.2 km
  • Bean Point Beach - 3 min walk - 0.3 km
  • Anna Maria City Pier - 16 min walk - 1.4 km
  • Anna Maria Island Museum and Historical Park - 18 min walk - 1.6 km
  • Bradenton Beach - 5 min drive - 3.4 km

Getting around

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

Restaurants

  • ‪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
  • ‪North Shore Cafe - ‬16 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.

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

No, pets are not allowed at this 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, just steps away from Bean Point Beach and Anna Maria Beach. Palmetto Avenue Beach and Bayfront Park are also within 10 minutes.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 184 out of 187 reviews
Rating 8 - Good. 2 out of 187 reviews
Rating 6 - Okay. 0 out of 187 reviews
Rating 4 - Poor. 1 out of 187 reviews
Rating 2 - Terrible. 0 out of 187 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Verified traveller

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

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

10/10 Excellent

TAMMIE R., LUTZ

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

10/10 Excellent

Sallie F., Bradenton, Florida

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

Great fun despite the rain

Even though there were a lot of rainy days, we loved the house and all the amenities. Beautifully furnished with so much to do, we enjoyed every day. The owners are lovely people and make sure everything is taken care of.
Stayed 7 nights in Aug 2019

10/10 Excellent

Martha M.

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

Perfect!

Had a fabulous time at Dragonfly! The house, pool and proximity to the beach was absolutely perfect! Very nicely appointed house! Hope to come back next year!
Stayed 5 nights in Apr 2021

10/10 Excellent

Verified traveller

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

Great time!

We had an awesome time at Dragonfly! It is a perfect house for hanging out with family. Close to the beach, close to the restaurants, etc. And the house itself has everything you need: great kitchen, outdoor space, pool and hot tub, beach equipment, ping-pong, multiple refrigerators / freezers, laundry, etc. Amazing place. And great and timely service too.
Stayed 9 nights in Dec 2019

10/10 Excellent

Susan L., USA

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

Heaven on earth

There are no words to describe this home. It’s perfection. It’s our second stay here and I’ve already rented it for 2021.
Stayed 9 nights in Mar 2020

10/10 Excellent

Sarah W.

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

Another Perfect Stay at Dragonfly!

Our family had a fantastic week at Dragonfly - our 5th year! House is lovely and has every possible amenity you could need. We love Bean Point Beach and you can not beat Dragonfly's location for beach access. Pool and hot tub, plus bikes, ping pong, foosball and putting green kept all occupied happily during our non-beach time. Property managers are wonderful and so helpful and communicative. We have made such wonderful memories here and hope to return next year!
Stayed 7 nights in Oct 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Katie C.

Outstanding location for a family vacation!

I had the pleasure of staying at the Dragonfly with friends and family from 3 generations for a week-long vacation. The house is beautifully decorated and equipped with everything you need to have a great time, whether you are 5 years old or 75 years old! We enjoyed the house so much that we ended up rarely leaving. The kitchen had every cooking tool we needed; the supply of games, pool toys, bikes etc. kept everyone happily occupied; and maintenance issues were addressed quickly and professionally by the property manager.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Tony P.

Fabulous!

This is a beautiful home! Attention was paid to every little detail. Jeffrie is an absolute pleasure to deal with. We will definitely be back! Thank you Jeffrie!
Stayed 5 nights in Apr 2017

10/10 Excellent

Heather M., Knightdale, United States

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

Wonderful Vacay!

This home is everything our family and friends could have asked for this week. The owner and property manager are responsive to questions and have thought of everything. Pack your suitcase and you will be ready! The walk to the beach wasn’t too bad but, if you have younger kids it could be. Can’t wait until next year!!
Stayed 7 nights in Jul 2020

10/10 Excellent

Tim L., Columbus, Ohio

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

AMI's Finest

Our family had a truly magnificent time at Dragonfly. The owners have equipped their home with many well thought-out amenities which resulted in hours of enjoyment during our stay. The Dragonfly home, the pool, the location, the town, the hosts (Dan and Goose) were all top notch. It was a wonderful week from start to finish. A big "thank you" to all who helped make that happen.
Stayed 7 nights in Jun 2023

10/10 Excellent

Stasha J.

Truly fantastic

The house is impeccable and it really had everything our family needed for our 5 day stay. The kitchen is perfect for cooking and has all updated appliances. The property is across the street from the beach, and it’s not a bad walk at all for the kiddos either. The pool is heated and the jacuzzi is awesome for cooler days and evening dips. It is truly the best vacation rental we have ever visited and we love going back every year. Thanks to Jeffrie for his unparalleled hospitality!!!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Eva C.

The house and amenities were fantastic and exceeded our expectations!

The gourmet kitchen was fully stocked and all bathrooms were beautifully appointed. The family enjoyed playing ping pong, corn holes and swimming in the pool. The beach was just a short walk and wagons provided made transporting toddlers & provisions much easier. Our older kids has lots of fun with the provided boogie boards. Everything was in perfect shape except for the beach umbrella. I would highly recommend this property to anyone with a large active family.
Stayed 5 nights in Jul 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Stephanie f.

Absolutely AMAZING!

We had such a wonderful experience at the dragonfly. From the first interaction with the homeowner to the last, we couldn't have been more impressed. Traveling with 4 small children we had numerous questions and concerns. Every question was met with a quick answer and opportunity to make our stay more accomadating. We have never experienced such professionalism With regards to the property. There was no stone left unturned. It was beautiful and we couldn't believe how much time and thought went into making our stay one to remember. All the rooms had such beautiful furniture and decorations. . The outdoor space and pool area were equally breathtaking. We could not have been more pleased Dragonfly thank you for making our family vacation one filled with memories for a lifetime. We hope to continue our memories there again in the future.
Stayed 6 nights in May 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Mitch S., Belle Vernon

AMAZING property!! Spacious, modern, comfortable

Dragonfly exceeded our expectations in every way! The house was immaculate and was very well maintained. The WOW factor was everywhere from the gourmet kitchen with high end appliances to the many amenities found in every room and throughout the house and the property. We ate in every night because we didn't want to leave the property and that included a dinner prepared by a private chef and then the fishing catch that my family members caught and then prepared after a morning of shallow water and deep sea fishing. The ocean was a 6 minute walk even with us pulling a beach wagon loaded with sand toys, chairs, umbrellas, etc. The swimming pool was perfect to relax in and around while others played ping pong and bocce. I will definitely recommend this to everyone I know who wants a first class vacation experience. My entire family was impressed and so was my wife and I. If I could rate it higher than a five star plus I certainly would!!!!!

10/10 Excellent

Marcy R., Rossburg, OH

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

Everything you could think of and more!!

This was a fantastic vacation and this home was perfect for our entire family. We had reserved this about 2 years ago and during that time we lost two family members unexpectedly. So this was a wonderful family time to enjoy and appreciate all we have and come together with our kids and grandkids. This home had EVERYTHING, and I mean EVERYTHING we could need and more. There were sand toys, chairs, umbrellas, kayaks, beach wagons, cooler, bikes, helmets, games of all kinds and wonderful indoor and outdoor gathering areas that our family made full use of. The home was beautifully decorated and the amenities were all there. Really you only needed to pack your clothes (and swim wear). Nice location and easy access to beach and nearby piers. It was extremely hot while we were there and stormed a few times, but there were plenty of games for us to enjoy inside or on the porches. The property managers checked on us first day and also after one of the storms. We were given a bottle of wine and a gift certificate for the nearby ice cream store...very nice welcome gifts. Thank you. Our family is already talking about booking this home again.
Stayed 7 nights in Jul 2022
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Patricia P., Coral Springs, Florida

Perfect Family Time Vacation

Our family vacation at Dragonfly was wonderful from the moment we arrived. With my kids living in different areas, a family vacation is more to get them to spend some time together. For me, it was heaven, to have everyone under one roof for a week. Jeffrie’s home is absolutely gorgeous and very comfortable. It’s not a typical “beach house rental”. It’s a home that one is very proud of and so well taken care of. The detail of the decorating was impeccable. Jeffrie or Josh were accessible by phone or email with any concerns before or during our stay. We had an amazing time and absolutely loved everything about Dragonfly. Everything exceeded our expectations. From the fabulous pool area and all it's amenities, the amazing gourmet kitchen, a cook’s dream, to the spacious living area, the comfort of the beds, linens, plenty of towels, and the color scheme were all part of the experience. The kitchen was stocked with a wine cooler, great pots and pans and utensils, and it being a part of the living area, made cooking for my family lots of fun, because everyone was gathered around, critiquing as I prepped for our meals. We enjoyed family dinners together every night at a beautiful dining room table, using the lovely table linens. However, we did BBQ for the 4th and the BBQ was also top shelf. Dragonfly is in a wonderful location, close to beach, shops, and restaurants and apparently, Island Coffee makes the best espressos, according to my husband and sons. Also, do NOT miss The Donut Experiment. You get to make your own donut with awesome toppings. Riding bikes around the Island was a great way to see all the nooks and crannies the Island has to offer. The beach is beautiful and the sunsets don't get any better than Florida’s west coast, especially in this part of Anna Maria Island. We tried to get down to see the sunsets every evening. We were there during the week of July 4th , so we were able to watch the fireworks display from the beach and there were a few going on around the Island. The only down side to this vacation was a week was too short. We are actually looking to book Dragonfly again next year and extend our time. They say a home tells a story and is a reflection of who you are and a collection of what you love, as well as style, which reflects your personality. Jeffrie, your home speaks volumes of the person you are! Thank you for sharing your beautiful home with my family. Until next time! Live, Love, Laugh! Pat

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

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

10/10 Excellent

Ray G.

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

AMI star

We have rented several houses on AMI and this was by far the best. The location to the beach and the house itself are just great. But the attention to detail of what renters might need in a beach house was top notch. The bikes, the beach toys and equipment and the kitchen supplies, the games, the towels and pool equipment made our stay so easy and luxurious. This property is so great for kids with the putting area, the spa tub, the ping pong table and lots of other yard games and balls. We had great check-in help and when we needed help with the pool temp we had immediate response from the management team. Really, there’s not one negative thing to say. Thank you for this lovely stay.
Stayed 7 nights in Mar 2025

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

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

10/10 Excellent

steve c.

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

Annual Visit to AMI

Me and my family have been staying in December at AMI about 7 years consecutively with 4 of those at Dragonfly. We all had a great time again this year. The house is in excellent condition with all the nice amenities as usual. We enjoyed the usual activities at AMI. We spent lots of time at the beach and walking to the shops and restaurants. The property managers Goose and Dan were great to work with as usual. They were very responsive always especially when we needed the combinations to the bike locks :). Its a great house, location, and great support system.
Stayed 10 nights in Dec 2024

8/10 Good

Kerry T.

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

Family return to Anna Maria

Wonderful house, beautifully kitted out, equipped with everything you might need! The property managers were extremely helpful and responsive. The only very small negative is that because of the location of the house and the amount of development work currently underway, it was occasionally noisy around the pool area during the day - although this wouldn’t put us off returning to the property.
Stayed 7 nights in Aug 2024