See all properties
Entire home

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 82884 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View in a map
Anna Maria, FL
  • Place, Bean Point Beach
    ‪2 min walk‬
  • Place, Anna Maria Beach
    ‪2 min walk‬
  • Place, Bayfront Park
    ‪7 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 Single 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.
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.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

The beach? The pool? Spoil yourselves and have both!
Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!
  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
10.0 out of 10, Exceptional, (141 reviews)
Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!

House Rules

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

Children

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

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

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.
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

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

We should mention

A car is recommended for transport to and from this property

About the area

Anna Maria

Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Travelling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Anna MariaOpens in a new window
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
  • ‪Anna Maria Island Beach Cafe - ‬10 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 5 Mar, 2026, prices found for a 1-night stay for 2 adults at Dragonfly - Southern charm on the North end of Anna Maria Island on 9 Dec, 2026 start from S$1,585, 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 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 186 out of 189 reviews
Rating 8 - Good. 2 out of 189 reviews
Rating 6 - Okay. 0 out of 189 reviews
Rating 4 - Poor. 1 out of 189 reviews
Rating 2 - Terrible. 0 out of 189 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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
This review was submitted before 2018 and can't be 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

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

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

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

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

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
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Victoria J.

Perfect location, excellent decor, very roomy. Every potential need has been anticipated.

We were so pleased we have booked again for next year. Every possible need has been anticipated. Kudos to Jeffries!
Stayed 6 nights in Jul 2017

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

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals