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

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Fridge, microwave, oven, stovetop
Smart TV, fireplace, DVD player, ping pong
Beach nearby, sun-loungers, beach towels
Fridge, microwave, oven, stovetop
Exterior

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 8268 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace

Explore the area

View map
Anna Maria, FL
  • Anna Maria Beach
    ‪2 min walk‬
  • Bean Point Beach
    ‪3 min walk‬
  • Bradenton Beach
    ‪6 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪42 min drive‬

Room options

About the area

Anna Maria

A family-friendly stay in Anna Maria awaits you at this holiday home. Within steps you'll find popular attractions like Bean Point Beach and Anna Maria Beach. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .You can enjoy Smart televisions with a DVD player, and home features free WiFi, 3.5 bathrooms and a fireplace. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A balcony or patio, a living room and a fenced private garden are also available. Housekeeping is available on request. .This smoke-free holiday home offers a garden and barbecues. Added amenities include a hot tub and laundry facilities. .Attractions within a 30-minute drive of this Anna Maria holiday home include Coquina Beach and IMG Academy.
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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 - 6 min drive - 3.4 km

Getting around

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

Restaurants

  • ‪The Sandbar Restaurant - ‬3 min drive
  • ‪Hurricane Hanks - ‬8 min drive
  • ‪The Waterfront Restaurant - ‬17 min walk
  • ‪Ginny's & Jane E's - ‬3 min drive
  • ‪Harry's Grill - ‬20 min walk

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.

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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

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

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

Frequently asked questions

Are there any beaches close to Dragonfly - Southern charm on the North end of Anna Maria Island?

Yep, Dragonfly - Southern charm on the North end of Anna Maria Island is a short 1-minute walk from Bean Point Beach. Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find water sports equipment and motor boats.

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

Dragonfly - Southern charm on the North end of Anna Maria Island has a heated pool and a pool.

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

This property features a heated pool, as well as a private pool and a fireplace.

What makes Dragonfly - Southern charm on the North end of Anna Maria Island a romantic place to stay?

1 hot tub, private pools, and fireplaces all help set the scene for a sizzling getaway at Dragonfly - Southern charm on the North end of Anna Maria Island.

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

You bet! With amenities such as a playground and laundry facilities, as well as highchairs and children's dinnerware, it's no surprise that Dragonfly - Southern charm on the North end of Anna Maria Island is a winner with our family travellers.

Is there a private hot tub at Dragonfly - Southern charm on the North end of Anna Maria Island?

Yep, there is a hot tub.

Is there a free airport shuttle available at Dragonfly - Southern charm on the North end of Anna Maria Island?

No, Dragonfly - Southern charm on the North end of Anna Maria Island does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Dragonfly - Southern charm on the North end of Anna Maria Island?

No, pets are not allowed.

Reviews

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

10

Exceptional

10/10

Cleanliness
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

Reviews

10/10 Excellent

elena g.

Liked: Cleanliness
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

10/10 Excellent

Nick Rowe

Liked: Cleanliness

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

10/10 Excellent

Verified traveller

Liked: Cleanliness

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

betty Q.

Liked: Cleanliness

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., USA

Liked: Cleanliness

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

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

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

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

Paul R.

Liked: Cleanliness
Stayed 5 nights in Dec 2024

10/10 Excellent

steve c.

Liked: Cleanliness

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

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

10/10 Excellent

gt a.

Liked: Cleanliness

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

Nancy C.

Liked: Cleanliness

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

10/10 Excellent

Holly F., Pennsylvania

Liked: Cleanliness

Paradise Awaits at Dragonfly!

We just returned home from a truly amazing vacation at Dragonfly. From the moment we arrived, we could tell that this property was the perfect choice for our family. The beautiful house was spotless, the condition of the property was impeccable, and it was very evident that much thought went into how to make a guest welcomed and valued. We found the 'extras' that were provided to be special and allowed our family to relax and focus on the special time we had there together. We especially enjoyed the amazing pool area, grilling at the outdoor kitchen area, the fantastic bikes, and all the added touches that often are not offered at a rental home. All amenities were in tip-top shape, giving us so much to do and enjoy during our vacation. We have stayed on AMI several times over many years, and this home and property exceeded all others. The property managers, Goose and Dan, were highly attentive and very personable; they responded quickly to any communication we had with them, both before and during our stay. We look forward to being able to visit Dragonfly again for another glorious getaway! Thank you for sharing your beautiful home with us!
Stayed 7 nights in Jun 2024

10/10 Excellent

Debbie K.

Liked: Cleanliness

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

10/10 Excellent

Jeannine S.

Liked: Cleanliness

Oasis

I have stayed at several properties at AMI. This by far exceeded all of them. The home and amenities are top notch. Items are labeled and extremely organized. Little things like kleenex, condiments and surplus of trash bags were included. We truly only needed to concern ourselves with food and beverages. Homes like this should be the norm!!!
Stayed 7 nights in Apr 2024

10/10 Excellent

Susan L., USA

Liked: Cleanliness

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

10/10 Excellent

Debbie H., Geneva, Illinois

Liked: Cleanliness

Best Family Vacation

We had an amazing time at Dragonfly. The house, location, and property manager was absolutely perfect. The house had everything from bikes to old bay seasoning. The management team thought of everything. We hope to be back soon. Such a wonderful family vacation. Thank you!
Stayed 4 nights in Jan 2024

10/10 Excellent

steve c.

Liked: Cleanliness

AMI Dragonfly

Dragonfly is an excellent residence, nice furniture, well equipped, great floor plan, good location, very well managed and maintained. No complaints
Stayed 13 nights in Dec 2023

10/10 Excellent

Tami H.

Liked: Cleanliness

A Treasure on Anna Maria Island

Dragonfly is the perfect beach home for a family vacation! Everything from the fabulous pool with all the toys, the putting green, bikes for all, and game room were planned with fun in mind! The kitchen was incredibly stocked with all the necessities, and all the bedrooms were roomy and extremely comfortable. And it is just steps away from the most beautiful stretch of beach on the island! The description was accurate, but we were still pleasantly surprised by this lovely home. Our family loved our time at Dragonfly and the warm welcome upon arrival. We will definitely come again! Best vacation home for a lovely stay at the beach.
Stayed 4 nights in Dec 2023

10/10 Excellent

Wayne C.

Liked: Cleanliness

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

10/10 Excellent

Sarah W.

Liked: Cleanliness

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

10/10 Excellent

Lynn G.

Liked: Cleanliness

Great Rental

This is our second year in a row staying at Dragonfly. The house is beautiful and the management team is exceptional! They are so friendly and approachable! It’s refreshing to have actual people to talk with instead of answering machines as we had with other rentals in the past. They reached out to welcome us and responded immediately to any questions and concerns we had.
Stayed 7 nights in Jul 2023

10/10 Excellent

Tim L., Columbus, Ohio

Liked: Cleanliness

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

Ina G., Medina, Ohio

Liked: Cleanliness

Beautiful!

Our family loved our stay. The house was very well appointed and comfortable.We enjoyed the quick access to the beach and the heated pool. The gourmet kitchen was an absolute delight. The house, deck and other outdoor spaces had an abundance of comfy furniture and plenty of tables which we appreciated. Another wonderful amenity was the rolling screens for the upper deck, they made it possible for us to be comfortable when the sun was on the west side of the house. We would definitely stay here again
Stayed 7 nights in May 2023