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
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
Property Registration Number DWE5105163
About the area
Holmes Beach
Holmes Beach is home to this apartment. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. 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
Anna Maria City Pier - 3 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive
Restaurants
Anna Maria Island Beach Cafe - 6 min drive
The Ugly Grouper - 4 min drive
The Sandbar Restaurant - 17 min walk
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 Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island?
As of 7 Apr, 2026, prices found for a 1-night stay for 2 adults at Gulfside 1Br/1Ba Captain's Quarters On Anna Maria Island on 1 May, 2026 start from S$244, 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 a 10-minute walk of Bradenton Beach and Palmetto Avenue Beach. Island Players and Anna Maria Island Museum and Historical Park 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 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 Jul, 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 Jun, 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 Jun, 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.
Unser Aufenthalt bei Barbara Kitchel war ganz einfach wunderschön! Die kleine Wohnung verfügt über viel Charme und ist in allerbester Lage!!! (50 m zum Strand) Es hat alles, was man braucht. Die Terrasse ist der absolute Hit- wunderschön!!! Wir haben unvergessliche Abendstunden da verbracht. Barbara Kitchel ist eine freundliche bemühte Gastgeberin. Vielen Dank für alles!
Daniela E.
Stayed 11 nights in Apr 2022
Response from VrboOwner on 28 May, 2022
Danke! Bitte, kommen sie wieder. Mit lieben aus Astro. Wir schreiben bald nach Astro's besuch mit die veterinarian.
Barbara und des hunden Astro und Hera
We had a great 1 week vacation at this property. It is located near the path to the beach and we enjoyed riding the bikes provided all over the island! When we called our host to tell her that the microwave had stopped working she purchased another one and replaced it in hours (even though we told her it wasn't necessary). Thanks for a great vacation!
My stay at captains quarters was absolutely wonderful! It was very peaceful! The accommodations was exactly what I wanted! A nice small unit that I required! The access to the beach was just a few minutes walk!! Thanks Barbara for your hospitality!
Wonderful property right on the beach. Had a great vacation. Barbara was a wonderful host. Thought we had a issue with refrigerator and Barbara attended to immediately. We definitely would stay again.
Pamela V.
Stayed 8 nights in Oct 2021
Response from VrboOwner on 23 Oct, 2021
So glad you enjoyed staying in Captain's Quarters and that you and your daughter had a relaxing week. We try to make our little place a quiet getaway despite being close to the more crowded motels and restaurants of downtown Holmes Beach. Please come again or if you visit nearby stop by and say hello.