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Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel

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Private kitchen
Exterior detail
Terrace/patio
Property grounds
Terrace/patio

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Parking available
  • Air conditioning
  • Dryer
  • Washer
  • Outdoor space
  • Kitchen

Explore the area

Map
Anna Maria, FL
  • Anna Maria Beach
    ‪2 min walk‬
  • Bean Point Beach
    ‪7 min walk‬
  • Anna Maria City Pier
    ‪11 min walk‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪38 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

2nd Bedroom

1 Queen Bed

Master Bedroom

1 Queen Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Hair dryer

Spaces

Porch or lanai
Kitchen
Garden
Dining area

About this property

Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel

The Barefoot Gypsy is an enchanted cottage tucked in the north end of Anna Maria Island in the City of Anna Maria, .Florida, mere steps to the white powder sands of Tampa Bay leading to Bean Point and the Gulf of Mexico.

For a taste of Old Florida Charm, meander a few steps to the Rod & Reel Pier, built in 1947. This is a favorite of locals and visitors alike to see dolphins, manatee, and an abundance of shore birds. If you are looking for a special place to dine on local fare, you won't be disappointed.

:Beautifully decorated, the cottage features two large bedrooms with queen beds in each room. Also, a large hall bath with a separate shower and tub, a half bath off the master bedroom, and an updated fully equipped kitchen are creatively appointed. The original terrazzo floors are flawless! There is also a bonus room with work space/art space and a full sized washer and dryer. Four bikes, beach wagon, beach chairs, beach umbrella, and beach towels, and a propane grill are also provided.

The living room, dining room, and kitchen along with a vaulted ceiling are covered with reclaimed wood from an original cottage on Bean Point. Just outside the front door, a delightful porch area is the perfect place to grill up your fresh catch or to sip coffee or wine and simply watch beach goers stroll by. .

The Barefoot Gypsy will be a home to revisit through the years for rest and relaxation and especially to take a step back in time and experience the charm of a true beach cottage.

I welcome you to the cottage and hope you will feel the warmth and charm I share with you. Welcome! "The Barefoot Gypsy"

Property manager

Glenna Walton

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

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

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Quiet time on the island is from 10pm to 8am and is strictly enforced by law enforcement. Violations will result in fines and eviction from property.
No lights (except red) allowed on beach at night during turtle nesting season (May1-Oct 31). This includes flash photography and flashlights.
Bicycles, pets, and golf carts are not allowed on the beach. Remove all umbrellas, chairs, etc. from beach and fill in holes upon departure.

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 are no carbon monoxide detectors or gas appliances 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 not required for transport to and from this property

About the area

Anna Maria

Located in Anna Maria, this cottage is near the beach. The area's natural beauty can be seen at Anna Maria Beach and Bean Point Beach. AMI Paddleboard Adventures and Fish Hole Adventure Golf are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Anna Maria, FL

What's nearby

  • Anna Maria Beach - 2 min walk - 0.3 km
  • Bean Point Beach - 7 min walk - 0.6 km
  • Bradenton Beach - 8 min walk - 0.7 km
  • Anna Maria City Pier - 11 min walk - 1.0 km
  • Anna Maria Island Museum and Historical Park - 15 min walk - 1.3 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 38 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬9 min drive
  • ‪Rod & Reel Pier - ‬1 min walk
  • ‪Two Scoops - ‬11 min walk
  • ‪Sandbar Seafood & Spirits - ‬3 min drive
  • ‪The Waterfront Restaurant - ‬12 min walk

Frequently asked questions

Is Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel?

Check-in begins at 4:00 PM.

What time is check-out at Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel?

Checkout is at 10:00 AM.

Where is Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel located?

Situated by the sea, this cottage is within a 10-minute walk of Anna Maria Beach and Bean Point Beach. Bayfront Park and Bradenton Beach 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. 35 out of 35 reviews
Rating 8 - Good. 0 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Tina B.

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

First time on the Gulf

Great house, great location, great weather!
Stayed 5 nights in Mar 2025

10/10 Excellent

Sarah F.

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

Amazingly Cute Cottage

The Barefoot Gypsy is a gem. It is super cute and recently fully remodeled post hurricanes. It is totally adorable with great finishes and is also super clean. The location is excellent and the managers were very friendly and helpful. I could not recommend it more.
Stayed 3 nights in Feb 2025

10/10 Excellent

Jeffrey F.

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

Anna Maria cottage

Great cottage with all the amenities. Loved that is was close to the beach and kept very clean. Also had beach supplies available. Loved our stay.
Stayed 6 nights in May 2024

10/10 Excellent

Regena R.

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

Cute place! Very cozy and relaxing place to stay!

We all Love the little cottage! Had everything you would need to go and enjoy the beach! Cottage was supplied with everything you need in a home from bathrooms, kitchen and grilling equipment! This is a 5 star cottage! Will definitely stay here again! Loved It!!!❤️❤️❤️
Stayed 3 nights in May 2024

10/10 Excellent

Tina H.

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

Anniversary Trip

Everything about this cottage was absolutely perfect! We Loved it !
Stayed 6 nights in Jun 2023

10/10 Excellent

Tracy S.

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

Perfect

Loved our stay. Everything was perfect.
Stayed 4 nights in Jul 2023

10/10 Excellent

Scott B.

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

Another delightful visit

This was our second time at this location. Very comfortable and peaceful. Lots of amenities and very responsive management. Excellent location. A short stroll to a nice big white-sand beach. Very few people on the beach, too. Rod and Reel Pier right across the street. The perfect place for an island get-away!
Stayed 5 nights in Dec 2023

10/10 Excellent

Erin R.

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

Lovely Cottage

My mom and I had a wonderful stay at the cottage! Close to the beach, clean, and cozy with lovely ambiance. It had brand new furniture that we enjoyed settling in on at the end of our fun days out on the beach or shopping. Plenty of gear to get to and from the beach with ease. We hope to be back!!
Stayed 4 nights in May 2023

10/10 Excellent

Donald C.

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

AMI- Barefoot Gypsy

Cozy, clean and conveniently located! Plus has all of the extra amenities that one would need. The bottle of wine upon our arrival also a very nice touch! This was our second visit to AMI and again chose the Barefoot Gypsy.
Stayed 7 nights in Feb 2023

10/10 Excellent

Margaret W.

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

Perfect location

My husband and I and our two 5 yo thoroughly enjoyed our stay at Barefoot Gypsy. The location is perfect! It's right across the street from the beach and pier. It's set away from the shops so there isn't a crowd but close enough to shops and restaurants that it's not an inconvenience either. The house itself is stocked with everything you need and even additional small conveniences that we much appreciated. The bonus room was a fun play space for the kids. We would stay there again without hesitation!
Stayed 4 nights in Jul 2023

10/10 Excellent

Mira D., Apollo Beach , FL

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

I am not a writer

Excellent
Stayed 4 nights in Apr 2023

10/10 Excellent

Kathi W., Nashville, TN

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

Barefoot Gypsy exceeded our expectations/hopes

We loved our stay at the Barefoot Gypsy. The property is a well-kept, cozy home just steps away from the beach. The courtyard was ideal for reading in the shade. The living area was comfy. The kitchen was the best equipped I've had compared to other rentals. The bathrooms were clean and functioned well. Dan and Goose (property managers) were super responsive in answering our questions and quickly attending to a minor issue. Having beach chairs, an umbrella, and bikes at our disposal added greatly to our enjoyment of our time there. Bean Point is a great location where one can enjoy the Bay and the Gulf. We will be back.
Stayed 6 nights in Mar 2023

10/10 Excellent

Connie H.

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

Wonderful Getaway

My husband and I truly enjoyed our stay at Barefoot Gypsy! Most charming and immaculate is the best way to describe her. The property seemed larger than pictured which was a bonus. We did not cook during our10 day stay but the kitchen was well stocked with anything we would need. We loved sitting on the front patio with lighting in the early evening. Late evening mid-March was quite chilly so we headed indoors and made good use of the pillows on the sofa and chairs. There was plenty of seating for two but not very comfortable. We enjoyed the convenient Rod and Reel Pier/Restaurant being a two minute walk from the cottage. It is a great place with good food and atmosphere. I would like to mention to anyone looking for a "real" beach vacation the beaches with closest proximity (across the street) to Barefoot Gypsy may not be exactly what you are looking for i.e. a nice sandy beach. Bayfront Park, with decent parking (or 12 min. walk), might be a better option. Keep in mind you are on the Tampa Bay side of Anna Maria Island and there is quite a difference compared to the Gulf side. Bean Point Beach is another option but we did not have the opportunity to visit. While at Bean Point we attended an excellent performance at Island Players Theater, only a 5min. drive from the cottage. There are many eatery options in this area as well. If time permits we highly recommend a day trip to Sarasota to the Mote Aquarium and the Discover Sarasota Trolley Tour. We thoroughly enjoyed this relaxing 10 day getaway at The Barefoot Gypsy in Bean Point where we were able to do as much or as little as we liked.
Stayed 10 nights in Mar 2023

10/10 Excellent

Scott B.

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

Relaxing get-away

The Barefoot Gypsy was a perfect get-away home -- lovely, very clean, comfortable, and close to the beach and restaurants. The home had everything we needed for our stay. We will definitely come back to this charming, aesthetically pleasing home!
Stayed 5 nights in Dec 2022

10/10 Excellent

Kaelli K.

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

Great beach cottage!

We truly enjoyed our stay. The cottage was fully stocked with everything we could have needed even tho we brought some of the things just in case! Very clean and homey!
Stayed 4 nights in Jun 2022

10/10 Excellent

Juan B.

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

Long weekend getaway

Great location for easy access to both piers to go fishing. Beautiful sunset views within walking distance at Bean Point. Great place for a weekend away!
Stayed 3 nights in May 2022

10/10 Excellent

Ryan S.

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

Absolutely wonderful!

Clean, perfect, cozy. Felt like home. Everything was absolutely wonderful and perfect. Would highly recommend and would definitely stay here again!
Stayed 5 nights in May 2022

10/10 Excellent

Mira D.

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

I like it .

Excellent
Stayed 5 nights in Apr 2022

10/10 Excellent

Sara L.

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

Lovely!

This property is lovely! It is clean and updated and has so much to offer! Well and generously stocked - made our stay so easy. Location is great and it is such a quiet and cute neighborhood!
Stayed 4 nights in Apr 2022

10/10 Excellent

Kathy L.

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

Splendid in every way!

The Barefoot Gypsy is perfectly situated on the northern end of Anna Maria Island within moderately easy walking distance to restaurants, shops and the beach at Bean Point. We found the cottage very clean and well stocked with all the essentials for cooking and beaching. We felt perfectly at home the moment we stepped through the front door. The cottage has great charm and sets up for easy living. We felt like we were staying in a real home not some minimally furnished condo. An extensive guide to the area and the cottage itself are provided and the labeling on the light switches was greatly appreciated. Pictures are very accurate and the space seems larger than its actual square footage. Great experience working with the property managers and the owner. It was our first time to this area of Florida and we found the people very friendly. A nice sense of community here. Will definitely return again and am so pleased to have found this property.
Stayed 14 nights in Feb 2022

10/10 Excellent

Donald C.

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

Loved Barefoot Gypsy and AM Island

This was out first visit to Anna Maria Island and our stay at this home was great! Clean, comfortable, well supplied with just about anything one would need and great location on the north end. The owner(Glenna) and the property management company(Dan from Goose and Gander) were very responsive and helpful. Our plan is to return next year.
Stayed 4 nights in Feb 2022

10/10 Excellent

Mike/Bobi B., Plymouth

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

BEST AMI COTTAGE!!

Everything about this adorable cottage was prefect!!! Location, cleanliness, communication, 4 bikes, beach chairs, down to the wine and chocolates left for our arrival! We loved our stay so much… and we can’t wait to stay again at the Barefoot Gypsy!!!
Stayed 7 nights in Dec 2021

10/10 Excellent

Cheryl B.

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

Cozy Cottage

We really enjoyed our stay! We just loved it. Very cozy and was in walking distance of the Rod & Reel pier. Enjoyed watching the sunrise over the bay. The home has everything you need to enjoy your stay on Anna Maria Island. I would definitely stay here again.
Stayed 3 nights in Nov 2021

10/10 Excellent

Tricia W., Norwalk, Ia

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

Wonderful cottage in a great location

This cottage is very well maintained and matches the description. The owners have supplied their guests with all beach supplies that you will need. The cottage is across the street from the bay side and a short walk to the gulf side of the island. We spent more time at the gulf because the beach is bigger. We rented a golf cart and it was very helpful. We hope that the next time we visit this property will be available.
Stayed 4 nights in Jul 2021

10/10 Excellent

Becky D.

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

Perfect Cottage

We really enjoyed our stay! The house was perfect for our family. Kitchen was very well stocked. The location is fantastic!
Stayed 4 nights in Jun 2021

About the host

Hosted by Glenna Walton

Host profile image
My first visit to Anna Maria Island was almost twenty years ago. I knew upon arrival I would want to be connected to her forever.

Why they chose this property

During those years it was a very quiet community ~ the white sand beaches ~ riding my cruiser bike ~ exploring each neighborhood and getting to know the locals. I needed nothing more. Today it is much the same ~ beautiful white sand beaches ~ quiet neighborhoods ~ cruising through the neighborhoods ~ maybe a few more restaurants ~ but the magic and charm will never change.

My hope is that you will find the charm I found many years ago. Welcome to Anna Maria Island ~ please take care of our special island ~ leave her just the way you found her ~ we share the magic with you.

What makes this property unique

The amazing location of The Barefoot Gypsy on North Shore Drive is steps to Tampa Bay beaches and two short blocks from the incomparable natural beauty of Bean Point. These waters are bustling with wildlife on land, in the sea, and in the air. If you love dolphins, manatees, shore birds, sea turtles, and an abundance of fish, you will be thrilled!

The beaches boast amazing views ~ not only of the gorgeous blue/green clear waters - but also of Egmont Key, the Sunshine Skyway, Fort DeSoto Park and on most days the skyline of St. Petersburg. The shops and restaurants of Pine Avenue and Gulf Drive are also within walking distance of The Barefoot Gypsy.

Languages:

English