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

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A large, multi-story house with a swimming pool, multiple balconies, and a covered patio area.
A beach with clear turquoise water and white sand.
A two-story house with a swimming pool and outdoor seating.
A spacious living room with a fireplace, comfortable seating, a dining area, and a kitchen in the background.
A modern kitchen with white cabinetry, a stainless steel range hood, and a large island with bar stools.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 82884 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • 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.)
    ‪43 min drive‬

Room options

About the neighborhood

Anna Maria

This vacation home is adjacent to popular attractions such as Bradenton Beach and Bean Point Beach. The vacation home includes a private pool, a kitchen, and a fireplace.
View more Vacation Homes in Anna MariaOpens in a new window

What's nearby

  • Bradenton Beach - 1 min walk - 0.1 miles
  • Bean Point Beach - 2 min walk - 0.1 miles
  • Anna Maria Beach - 2 min walk - 0.1 miles
  • Bayfront Park - 7 min walk - 0.4 miles
  • Anna Maria City Pier - 16 min walk - 0.9 miles

Getting around

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

Restaurants

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

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. Occupancy regulated by the City of Anna Maria is eight persons regardless of age.

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.
The vacation home is air-conditioned and features a kitchen, 3.5 bathrooms, and a balcony or patio, and there's space to spread out with 5 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a fireplace. Housekeeping is available on request.

Similar properties

A hotel room with a bed, a sofa, a desk, a TV, a wardrobe, and a balcony with a view of palm trees and the beach.
Tropic Isle at Anna Maria Island Inn
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  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
9.0 out of 10, Wonderful, 740 reviews
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Oct 29 - Oct 30
Total with taxes and fees
Tropic Isle at Anna Maria Island Inn

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 transportation

  • Car recommended
  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bed sheets provided

Bathroom

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

Living spaces

  • Dining table
  • Fireplace

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

  • Smoking not allowed

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
  • Snorkeling 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)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

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 available
Minimum check-in age: 25

Check-out

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

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 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.

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

  • This property doesn't allow pets

Children and extra beds

  • 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
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

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

What is there to do near this vacation home?

This vacation home is located in Anna Maria, just steps from Bradenton Beach and Bean Point Beach, and within a short 1-minute walk of Anna Maria Beach. You'll also find Bayfront Park and Island Players less than a mile away.

Will I be able to park at Dragonfly - Southern charm on the North end of Anna Maria Island?

Yes, there is a garage.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

Is Dragonfly - Southern charm on the North end of Anna Maria Island good for couples?

There are many amenities for couples at this vacation home, including a private pool and a fireplace in each house, and some feature ocean view.

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

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does Dragonfly - Southern charm on the North end of Anna Maria Island have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Sarasota-Bradenton Intl. Airport (SRQ), which is 20.8 mi away (35 minutes by car). Another top airport is St. Petersburg, FL (SPG-Albert Whitted), which is around 17.1 mi away.

Can I book a room with a balcony at Dragonfly - Southern charm on the North end of Anna Maria Island?

Yes, every house at Dragonfly - Southern charm on the North end of Anna Maria Island comes with a patio and some offer ocean views.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 193 out of 196 reviews
Rating 8 - Good. 2 out of 196 reviews
Rating 6 - Okay. 0 out of 196 reviews
Rating 4 - Poor. 1 out of 196 reviews
Rating 2 - Terrible. 0 out of 196 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was my family’s best stay since we started coming to the island a decade ago. The communication and attention to detail is a cut above. Highly recommend this host and this property!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect property for a large family. Lots of activities and items to enjoy simply at the house. The beach is a stones throw away and the peekaboo views from the home are great as well. The home is well stocked and was very clean.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Couldn’t have been a better stay!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family has stayed at rentals all over the country, the dragonfly was by far the best! The thoughtfulness of the owners is excellent. The house has literally everything for a fantastic beach getaway and activities for the kids! 10 out of 10!
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best house we have ever rented. Hosts thought of everything and provided it. We stayed here with our 2 and 4 year old grandkids and there were booster seats, toys, crib options, AND the downstairs play space was a life saver in the coldest week we have ever spent in FLA.
Stayed 10 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dragonfly was in excellent condition, maintained spotlessly as usual. We had another memorable time there and appreciate the efforts by Goose and Gander Property Management to make sure we were happy with the house and amenities.
Stayed 10 nights in Dec 2025
Verified review

10/10 Excellent

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

Anna Maria stay at the dragonfly

My immediate family stayed at the house and my siblings with their families rented other homes closer to downtown Anna Maria
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location of this home for beach access and amenities was excellent. Quiet, peaceful and beautiful home. The pool is a plus with children and adds to the entire beach experience. The walk down the block to amazing sunsets with my family are memories we will have.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

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

Fantastic house and location!

Great house, great pool, Bean Point is the best beach in the world!
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

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

Family Vacation 2025

Dragonfly is a very well kept property in a very convenient location. Can’t wait to visit again
Stayed 7 nights in Feb 2025
Verified review

10/10 Excellent

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

Fabulous house and amenities

Our stay was great. The property had everything we needed for a wonderful family vacation and exceeded our expectations. We would certainly stay there again.
Stayed 7 nights in Jul 2024
Archival

10/10 Excellent

A royal vacation at the Dragonfly.

The Dragonfly thought of everything to make our stay wonderful. A beautiful property made us feel like royalty!!!
Stayed 5 nights in Sep 2017
Verified review

10/10 Excellent

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

Anna Maria July 25

a really excellent find, house in a great location, every toy you need all available.Any problems sorted by a very attentive manager.thoroughly recommended
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Wonderful Vacation Home

This home was beautifully decorated & equipped with everything you need for your stay. It is a short walk to the beach. Our family especially enjoyed the pool & big porch & patio areas.
Stayed 5 nights in Sep 2018
Verified review

10/10 Excellent

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

Dragonfly

We stayed at the Drafonfly for a full week. We couldn’t have been happier with the location, accommodations, cleanliness and presentation of the entire property. The site management Dan & Goose were always available and extremely nice! We highly recommend and will stay again!
Stayed 8 nights in Feb 2025
Verified review

10/10 Excellent

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

Perfect Place

We loved every minute of our stay at Dragonfly. We couldn’t have asked for more comfortable or more beautiful accommodations. It’s our new favorite!
Stayed 7 nights in May 2024
Verified review

10/10 Excellent

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

AWESOME

This place is everything is shows and more, our family enjoyed staying here and will be coming back to this property again!
Stayed 5 nights in Dec 2021
Verified review

10/10 Excellent

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

Perfect Family & Friends Getaway

This was the perfect hours for our 3 families to come visit AMI. We had adults and kids under 3 and the house set up was perfect. The owners thought of every detail for amenities, we can't wait to visit again!
Stayed 3 nights in Oct 2020
Verified review

10/10 Excellent

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

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

Terrific, loved it. Definitely a 5 star fun rental!!
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

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

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

It’s always the best vacation EVER! See you next June!!!
Stayed 8 nights in Jul 2021
Verified review

10/10 Excellent

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

Excellent Property

Anyone with small children to adults will love this property. The proximity to the beach was perfect. The rental company was amazing! We had such a good time, we have already booked for next year!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

absolutely the perfect beach house!

This is, by far, the best beach house we have ever rented. It is perfect in every way. A fabulous property - so very clean and comfortable. Every luxury your family needs for a perfect vacation.
Stayed 5 nights in Jan 2021
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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