Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island
Delightful private fully furnished one bedroom apartment on second floor of old Florida house located less than 100 feet from access to the white sand beach on the Gulf of Mexico. The spacious master bedroom is light and airy with windows allowing a peak at the Gulf of Mexico. There is a separate dressing area connected to the bedroom with a dressing table and two closets. The living room is paneled in old cypress with exceptional light from five windows, which overlook a natural landscape and provide a partial view of the water. The galley style kitchen is small but well-equipped and accesses a small pantry. The bathroom has a tiled shower and charming vintage washbasin. A bistro table on the deck outside the living room is ideal for outdoor dining while viewing the surrounding lush landscape and Gulf waters. Amenities include flat screen wall HD TV, oriental rugs over beautiful oak hardwood floors in the bedroom, WiFi, central heat and air, sunscreen shades in the living room and bedroom, a bedroom ceiling fan. You will enjoy the convenience of your own washer and dryer. A carport will protect your car from the Florida sun, and bikes may be provided on request to cycle around the island. Linens, kitchen ware, a coffee maker, iron and ironing board and a vacuum are provided. The furniture combines wicker and light solid wood pieces arranged for casual comfort. The living room sofa is long enough to accommodate an occasional overnight guest. A cushioned corner window seat in the living room is surrounded by windows on two sides. Anna Maria Island has wonderful shops and unique boutiques. There are restaurants for all tastes ranging from coffee bars to 5-star restaurants, all within easy distance driving, walking or biking. Captain's Quarters is in a home located in a residential neighborhood. All guests are asked to be good neighbors and maintain noise to a respectful level during day and night. Excessive and/or unreasonable noise can deprive neighbors of peaceful enjoyment of their property.
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The host requires you to complete the following before checking out:
Strip any used beds
Turn off the lights and return the keys
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Property Registration Number DWE5105163
Property # 491497vb
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Holmes Beach
Holmes Beach is home to this apartment. The area's natural beauty can be seen at Bean Point Beach and Bradenton Beach. Looking to enjoy an event or a game while in town? See what's going on at LECOM Park, or consider a night out at Tarpon Bay Grill and Tiki Bar. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling.
Anna Maria Island Museum and Historical Park - 2 min drive - 1.8 km
Bean Point Beach - 3 min drive - 2.4 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive
Restaurants
Anna Maria Island Beach Cafe - 6 min drive
The Sandbar Restaurant - 17 min walk
The Ugly Grouper - 4 min drive
The Waterfront Restaurant - 4 min drive
Ginny's & Jane E's - 14 min walk
Frequently asked questions
Is Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Captain's Quarters: Gulf views?
As of 7 July 2026, prices found for a 1-night stay for 2 adults at Captain's Quarters: Gulf views on 9 Oct 2026 start from AU$366, 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.
How much is parking at Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island?
On-site parking is available at the property.
What time is check-in at Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island?
Check-in begins at 4:00 PM.
What time is check-out at Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island?
Checkout is at 10:00 AM.
Where is Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island located?
Situated in Holmes Beach, this apartment building is within 2 miles (3 km) of Bradenton Beach, Bean Point Beach and Anna Maria Beach. Palmetto Avenue Beach and Island Players are also within 1 mile (2 km).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Barbara’s home continues to bring us back to AMI every year. The location to the beach, the cozy feeling, and the price can’t be beat. She has always been welcoming and offered many local suggestions to make the most of our visit. We always leave looking forward to our next visit. I would have zero hesitation recommending a stay with Barbara.
Dade R.
Stayed 8 nights in May 2026
Verified
6/10 Okay
Grace D.
17 Apr 2026
Liked: Check-in, communication, location
Very cute and perfect for two. Kitchen was very small though with some items broken and laundry is located outside. We enjoyed eating outside on the deck.
Wonderful!!! our host Barbara was amazing, always available if needed! Apartment was amazing! Perfect for two! Porch for outside dining. Kitchen is quaint, we had an amazing time. Steps to an amazing beach! Stayed a week and will definitely be coming back!Thank you Barbara for sharing your special home with us!
Barbara was an excellent host going above and beyond to make sure no details were missed. We felt welcomed and appreciated the whole time. She was also able to make recommendations on activities and restaurants that we feel were perfect to make the most of our stay.
Location was perfect, Barb was a perfect host, weather was great, the Room was clean with a 1950’s style with a lot of character similar to cottages in Michigan ..loved it our style
Loved the charming, quaint property. The location is perfect. Lots of windows let the light in and allow guests to enjoy the outdoors even on cool or wet days.
Relaxing week at Captain's Quarters for my wife and I. Convenient location for us with easy beach access and a short walk or bike to local restaurants and shops. We really enjoyed the second floor apartment and the outside deck. It was just right for us. Barbara is a great host. She's very easy to work with and she tries to make your stay comfortable and enjoyable. We would definitely return to this property in the future.
Alan C.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 1 May 2025
It is always a pleasure to have guests enjoy Captain's Quarters and the unique environment of Anna Maria Island's white sand beach. It would be an honor to have you visit again in the future perhaps during turtle season when there is opportunity to see the little hatchings hurry toward the Gulf at night guided only by star or moonlight reflected on the water surface. You were our Shell Drive (original name for our street) upstairs guests for only a short time but long enough for us to appreciate why we love to share our small beach home with visitors from colder states.
This was the perfect spot for our Mom/Daughter beach trip! The upstairs rental unit had the feel of a classic Old Florida beach bungalow. It felt like home by the end of our stay. The kitchen is tiny but we made it work for our needs. The beach access is just steps away, and the sunsets on AMI were the best I'd ever seen! Barbara is a wonderful host!
Tammy R.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 17 July 2024
Thanks Tammy. We would love to have you visit again in the future.
We had an amazing stay in Barbara’s quaint, Florida home. You are a short walk from the beach, able to easily come and go for walks, breakfast, or lunch. The ease of beach access makes this property an easy choice. Barbara was so kind and helpful during our stay. She made sure everything was taken care of, provided details, and made sure to give us the BEST food recommendations. She is a fantastic host. If you’re looking for a beach getaway, this is a great place to be.
Dade R.
Stayed 8 nights in Jun 2024
Response from VrboOwner on 20 June 2024
Thank you so much for being such perfect guests. We would love to have you visit again, Please give me a call anytime if you would like any news such as real time hurricane, red tide or construction information. We may be moving next year but can always provide recommendations and contacts with trusted locals. Have a safe and enjoyable summer.
Sincerely,
Barbara (with minor input from Asro, Hera and Terra)
Beautiful peaceful & quiet. Just what I was looking for.
The apartment is decorated so Beautiful.
Barbara is a wonderful host a very charming person.
I am blessed to have found such a place. I was truly in Paradise enshrouded in palm trees. The terrace is Amazing, and I loved eating there. The area is perfect close to everything. The beach a few steps away.
Small but charming apartment with lovely greenery surrounding and a small view of the Gulf. Short walk to beach. Nice bedroom with windows all around, and kitchen although quite small was adequate for us to prepare almost all meals. Barbara was lovely and very accomodating. Also loved having the bikes to go to Bean Point for sunset and to the courts for tennis and pickleball
patricia p.
Stayed 9 nights in Apr 2021
Response from VrboOwner on 24 Apr 2021
Thank you. You were lovely guests and I would love seeing you again.
This cozy upstairs cottage is just as it appears in the pictures. We found it to be very clean and comfortable, and a very short walk to the beautiful beach. All of the windows in the living area and bedroom reminded us that we were in a tropical paradise from sunup to sundown. The kitchen is tiny, but very workable. We cooked most of our meals in, but still enjoyed several local restaurants. Barbara is an excellent host, and we plan to return.
We loved this place. It has such old Florida charm. The bedroom is huge with tons of windows. We were able to hear the surf from bed ! The kitchen is small so we ate out a lot, but I was ok with that. The proximity to the beach is wonderful. It takes maybe a minute or two from the driveway to the beach. The host was wonderful and very helpful with any questions we had. I would definitely go back.
We enjoyed our stay at Captains quarters. It is an older property, as described in the listing, with character! We were surprised at how spacious the bedroom and living rooms were. We have stayed at several other places on AMI and have felt like we were cramped in the tiny bedrooms. Captains quarters was comfortable for us. The location is excellent. It took us about a minute to walk to the beach. It is also central to everything on the island. We enjoy breakfast at Genny and Jane e’s. We were able to walk there from Barbara’s place. We would stay there again! Barbara was also helpful and available as needed. We had a great vacation!
The home is nestled behind a row of bushes and flowers as a hidden quarter. The stairway is beside an outdoor shower. The furnishings are quaint. The deck provides a wonderful space. The view of the gulf is only found in certain areas due to the growth of palms.
The bedroom is light while the rest of the home is darker.
We don’t cook, but used the small fridge and really enjoyed the Keurig!
The walk to the beach is right next to the property. Our car stayed cool being parked under carport!
For two people who don’t do any cooking while on vacation and had no guests gave adequate space! The deck was my favorite space💗
Shannon L.
Stayed 7 nights in May 2021
Response from VrboOwner on 11 June 2021
Thanks for your comments. I always feel good when my guests tell me how much they enjoyed Captain's Quarters. The deck is definitely a popular hang out especially in early morning to enjoy the quiet and a cup of joe. Our family has enjoyed this place since its purchase in 1942 (!) so it does have some history. I am sure the "Captain" would be happy now to have his hideaway so appreciated. Take care and come again sometime for another visit.
Barbara is a lovely hostess, with a beautiful Floridian home, just a few yards from Holmes Beach. We absolutely loved our stay "On the Roof". Listen to the James Taylor tune. The terrace is wonderful, we drank coffee in the morning and sipped wine at night. You can see the Gulf from the bedroom window and the terrace. The second story of Barbara's home is cozy, with character and charm. Can't wait to go back. We'll remember this vacation forever ❤️
Contact free stay and the communication with owner was very prompt. She also accommodated our late arrival time. Location is excellent. It was easy to get to any place on the island via bicycle or the free trolley. We visited several beaches during our stay.