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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 - Dragonfly - Southern charm on the North end of Anna Maria Island (Anna Maria)
Smart TV, fireplace, DVD player, ping pong - Dragonfly - Southern charm on the North end of Anna Maria Island (Anna Maria)
Exterior - Dragonfly - Southern charm on the North end of Anna Maria Island (Anna Maria)
Beach nearby, sun-loungers, beach towels - Dragonfly - Southern charm on the North end of Anna Maria Island (Anna Maria)
Fridge, microwave, oven, stovetop - Dragonfly - Southern charm on the North end of Anna Maria Island (Anna Maria)
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

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer

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

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
Information provided by the property may be translated using automated translation tools

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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

  • 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
  • Anna Maria Island Museum and Historical Park - 18 min walk - 1.6 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.

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, 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

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

10

Location

Reviews

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

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

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

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

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

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

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

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

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

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
This review was submitted before 2018 and has not been verified.

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Stephanie H., Minneapolis, MN

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

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

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

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

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