Steps from Beach and Local Hotspots! Stay at Sunny Side Down!
Sunny Side Down by Anna Maria Vacations Duplex in Bradenton Beach, Florida VRC16-000153 / DWE5105831
Welcome to Sunny Side Down, a colorful and cozy duplex perfect for families or small groups seeking a tranquil beach escape! Located just three minutes from the white sandy beaches and a short trolley ride to Bradenton Beach shops, restaurants, and attractions, this two-bedroom, two-bath duplex offers a harmonious blend of comfort and convenience. Enjoy relaxing on your outdoor balcony before heading to the beach, with the included beach chairs, nearby water adventures, or the free island trolley for easy access to island fun!
Highlights • 3-minute walk to Cortez Beach • 2 Bedroom / 2 Bath • 1 King, 2 Twin Beds • Near trolley stop • Beach chairs and cart • In-unit washer and dryer • Dog friendly • Located near Bridge Street shops, dining, and attractions • 2 Parking Spaces
Spend sunny days lounging on the deck, soaking in the Florida sun, or taking your beach gear to the nearby shoreline. The outdoor area is perfect for relaxing or outdoor meals. The trolley stop, just steps away, makes it easy to hop on and explore all the island’s hotspots, including Bradenton Beach’s famous shops and waterfront eateries. When you’re ready for adventure, rent watercraft, fish, or simply enjoy the island’s natural beauty.
Inside, the bright, open layout radiates coastal charm with a welcoming atmosphere. Lounge comfortably in the cozy seating area, perfect for relaxing with family or friends. The fully equipped kitchen features island seating and a dining table for four, ideal for meals, conversations, and island-inspired fun. Large windows flood the space with natural light and fresh breezes that bring Florida’s outdoor beauty inside.
Retreat to the primary bedroom with a king-sized bed, a TV, and an ensuite bathroom with a shower/tub combo, offering a peaceful sanctuary for restful nights. The second bedroom, with two twin beds, is perfect for children or guests. The hall bathroom is similarly equipped with a shower and tub combo, providing guest comfort and privacy.
Room Details • Primary Bedroom (2nd floor): King bed, ensuite with shower-tub combo • Second Bedroom (2nd floor): Two twin beds
Book Sunny Side Down today and enjoy a tranquil, fun-filled beach vacation in beautiful Bradenton Beach. Whether exploring local hotspots, or strolling to the beach, this cozy duplex promises lifelong memories!
- Please note that there are nearby construction projects.
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details.
No cable, just smart TVs with streaming Apps.
2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.
This home is managed by Anna Maria Vacations, an Anna Maria Island property management company.
We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details.
Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
"St.Thomas" Villa: 2 Min Walk to Beach : Beach Gear: Tranquil Courtyard: 2BR/2BA
Bradenton Beach
"St.Thomas" Villa: 2 Min Walk to Beach : Beach Gear: Tranquil Courtyard: 2BR/2BA
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 and a deadlock
About the area
Bradenton Beach
Located in Bradenton Beach, this holiday home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Coquina Beach. Fish Hole Adventure Golf and Florida Maritime Museum at Cortez are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and ecotours nearby.
Historic Bridge Street Pier - 3 min drive - 2.1 km
Cortez Beach - 4 min drive - 2.4 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive
Restaurants
Anna Maria Oyster Bar on the Pier - 3 min drive
Daquiri Deck Bradenton Beach - 3 min drive
Anna Maria Island Beach Cafe - 4 min drive
Circle K - 20 min walk
Beach House Waterfront Restaurant - 18 min walk
Frequently asked questions
Is Steps from Beach and Local Hotspots! Stay at Sunny Side Down! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Steps from Beach and Local Hotspots! Stay at Sunny Side Down!?
As of 29 Sept 2026, prices found for a 1-night stay for 2 adults at Steps from Beach and Local Hotspots! Stay at Sunny Side Down! on 25 Oct 2026 start from AU$1,114, 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 Steps from Beach and Local Hotspots! Stay at Sunny Side Down!?
On-site parking is available at the property.
What time is check-in at Steps from Beach and Local Hotspots! Stay at Sunny Side Down!?
Check-in begins at 4:00 PM.
What time is check-out at Steps from Beach and Local Hotspots! Stay at Sunny Side Down!?
Checkout is at 10:00 AM.
Where is Steps from Beach and Local Hotspots! Stay at Sunny Side Down! located?
Situated by the sea, this holiday home is within a 5-minute walk of Anna Maria Sound and Bradenton Beach. Aluna Wellness Center & Spa and Bradenton Beach Marina are also within 1 mile (2 km).
Reviews
8.8
Excellent
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Amazing stat. Loved the unit and how close tot he beach it was. The host was awesome and very responsive. Will stay again!
Stayed 2 nights in Jun 2026
Response from VrboOwner on 11 June 2026
Having the beach so close makes every day on the island a little easier, Denisse. We're glad Sunny Side Down by Anna Maria Vacations was such a hit and that you enjoyed both the home and its great location. It's great knowing our team helped make your stay smooth and enjoyable with responsive communication along the way. Thank you for staying with us, and we’d love to welcome you back for another beach getaway soon!
Place was adorable and perfect for our stay. We were walking distance from beach and close to everything we wanted to do.
Stayed 2 nights in Dec 2025
Response from VrboOwner on 22 Dec 2025
Hi, Karen, thank you for staying with Anna Maria Vacations at Sunny Side Down and for sharing your experience. We are so happy to hear you found the home adorable and perfect for your stay and enjoyed being within walking distance to the beach and close to everything you wanted to do. We would love to welcome you back to Sunny Side Down for another Anna Maria Island getaway!!
Hi, Andrea, thank you for staying with Anna Maria Vacations at Sunny Side Down! We’re glad you enjoyed the great location. It’s a perfect spot for soaking up island vibes and getting around with ease. We’d love to host you again for another Anna Maria Island escape!!
Great location! Easy walk to beach. We had a couple of challenges upon check in but the property management team resolved very quickly. Had a wonderful time with family. Would definitely stay again!
Stayed 3 nights in Mar 2026
Response from VrboOwner on 17 Mar 2026
So glad to hear you had a wonderful family stay at Sunny Side Down by Anna Maria Vacations, Karen! Being just an easy walk to the beach really makes those days extra relaxing. We appreciate your patience with the check-in hiccups and are happy our team was able to get everything sorted quickly for you. Thanks so much for staying with us and we’d love to have you back for another easy, beachside getaway!
The location was close to the beach and restaurants. The house was clean and the host was responsive.
Stayed 2 nights in Nov 2025
Response from VrboOwner on 21 Nov 2025
Hi, Jeannine, thank you for staying with us at Sunny Side Down. We’re so glad you enjoyed the clean home, the responsive service, and the great location close to both the beach and local restaurants. It’s a perfect spot for easy island living. We hope to welcome you back soon with Anna Maria Vacations!!
House was fine, grill did not work, beach chairs went missing. communication was great with property management
Stayed 5 nights in Mar 2026
Response from VrboOwner on 14 Apr 2026
Thank you for staying with us at Sunny Side Down by Anna Maria Vacations and for sharing your feedback, Nora. We’re glad to hear communication with our team was a positive part of your stay. We’re sorry for the inconvenience with the grill and the missing beach chairs. Your notes have been shared with our team so these items can be checked and addressed for future guests. We appreciate you staying with us and hope to welcome you back again.
Everything was as pictured...No complaints from us.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 26 Dec 2025
Hi, Bryan, thank you for staying with Anna Maria Vacations and for sharing your feedback on Sunny Side Down. We’re so glad everything was exactly as pictured and that you had a smooth, no complaints stay. That’s always the goal. We’d love to welcome you back for another easy, relaxing island getaway next time!!
Overall, this property was adequate. Great location, but the rental “facilities” were not great. Specifically, there was a lack of seating (sofa was small), the support frame for one of the twin beds in one room was broken/did not provide needed support, the beach equipment was in poor shape (umbrella unusable, one beach chair broken), and there was not much of a patio to sit outside on.
Stayed 6 nights in Mar 2026
Response from VrboOwner on 8 Apr 2026
Thank you for sharing your feedback on Sunny Side Down, Doug. We’re glad you enjoyed the location; it’s definitely one of the highlights of this home. We’re sorry to hear some of the features didn’t meet expectations. Our maintenance team did inspect the beds and did not find any broken supports, but we appreciate you bringing this to our attention and will continue to keep a close eye on it. We’ve also shared your notes about the seating and beach equipment with our team so we can look into improvements. Thanks again for staying with us and for your helpful feedback.
Verified review
8/10 Good
Shelly C.
3 Apr 2025
Liked: Cleanliness, check-in, communication
1st Visit to Anna Maria Island
We were visiting for the first time. The house wss clean and it was an easy walk to the beach. We enjoyed our stay very much.
Stayed 4 nights in Mar 2025
Response from VrboOwner on 7 Apr 2025
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
Verified review
6/10 Okay
Mary E.
2 Mar 2026
Liked: Check-in, communication, listing accuracy
Windows weren’t cleanWalls needed a fresh coat of paintNo bedside tables
It was the first time for me. Everything was perfect. Location, communication, house in great condition and clean. I would do it again. Thank you
Stayed 5 nights in Dec 2025
Response from VrboOwner on 16 Dec 2025
Hi, Steve, thank you for staying with Anna Maria Vacations at Sunny Side Down. We love hearing that your first time was such a great experience and that the location, communication, and clean, well kept home all came together perfectly. That is exactly what we hope for every guest, and we would be happy to welcome you back anytime!!
This beach house was everything we hoped for and more! The space was clean and felt like a true home away from home. The kitchen was well-stocked, the beds were comfortable, and the bathrooms are spacious. The location couldn’t have been better—a very short walk to the beach. The hosts were incredibly kind and responsive, making the entire stay seamless from start to finish. We made so many great memories here and can’t wait to come back. Highly recommend!
Stayed 6 nights in Jun 2025
Response from VrboOwner on 18 July 2025
Hi, Alexis, thank you so much for your kind review! We are absolutely delighted to hear that you had such a wonderful experience at our beach house. It brings us great joy to know that the space, amenities, and location met all of your expectations. We truly appreciate your lovely feedback and look forward to hosting you again in the future. Your recommendation means a lot to us.
Thank you,
Anna Maria Vacations
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
Close to everything you could want to do, this was our first trip back after the devastation, nice to see and experience everyones spirits still up. Will be back soon. The one major thing I would make known are the laundry room code..we did not have access to the room for laundry or beach items, we had the door opened for us when we went to get the beach items the door was locked again
The house was so close to the beach and had all the beach ammenaties for us to use! The decore inside was a bit dated and dark. The beds were comfy. The downside was we were surrounded by early morning construction in rebuilding houses (I understand completely it has to get done, just a bummer to wake up to loud noises everyday). Also, the house directly behind us that the deck overlooks has a swimming pool that is being built but looks like a swamp and has lots of mosquitos so sitting on the deck wasnt an option.
Stayed 5 nights in May 2025
Verified review
6/10 Okay
Lindy C.
10 Apr 2026
Liked: Communication, location
This property was just okay. The best thing about it was the location/proximity and ease of getting to the beach. The lowest you can turn AC is 72, so it was hot for sleeping as well as during day when we were inside. One shower was almost unusable due to low pressure. Twin beds were very uncomfortable. Couch is the only sitting area in living room and it is very uncomfortable as well. Laundry accommodations were in first floor storage area- which is shared and I don’t feel this is communicated well in the description. We had Unit B and your deck area is facing another house and “alley” walking area. The picture of deck in gallery is Unit A.My biggest concern was employees (I assume) from rental management came in with out any notice to us from the company. One lady came in without even knocking. With teenage girls with us, this was scary to them. I also messaged for more towels and they were never delivered to us.So overall just ok, we enjoyed the island, but we will not rent this again.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 24 Apr 2026
Thank you for sharing your feedback on Sunny Side Down by Anna Maria Vacations, Lindy. We’re glad you enjoyed the location and easy beach access as it’s one of the best parts of the home. We’re sorry to hear some aspects of the stay didn’t meet expectations. Your notes about the A/C, seating, beds, and layout have been shared with our team for review. Regarding your concern about entry, we understand how that could feel unsettling. Our team does not enter occupied homes without notice unless there is an urgent situation, but we will certainly look into this further. For the towels, we received your request on the 3rd and they were delivered the same day, with a follow-up from our team to confirm. We appreciate you bringing these items to our attention and for staying with us.
Very clean and great location. Cons.. couch was unusable because it was so worn down. I’m not a heavy person but had to use bed pillows on the couch just to sit. The ceiling fan was almost un-usable. Severely off balance and had a loud tick that we had to turn it off or on low. Dishwasher did not clean. We had to get soap to hand wash only. Yes we did pre-rinse before using it. Honestly not a big deal for us as we had 4 adults to wash dishes :) The bottom shelf on the fridge was broken on one side and there were 2 door shelves that were missing. We had to use the master shower only because the spare shower was broken - only a dribble came out. Watch out for the light hanging in the corner.. really looks like it would fall out at any time. The upside it was a great location, very clean and the kitchen was beyond well stocked with everything you’d need to cook..
Stayed 4 nights in Nov 2025
Response from VrboOwner on 2 Dec 2025
Thank you for sharing your feedback! We’re so glad to hear you enjoyed the cleanliness, location, and well-stocked kitchen—that’s wonderful to know. We truly appreciate your detailed comments about the furniture and maintenance items. We’ve already scheduled an inspection to address the couch, ceiling fan, dishwasher, fridge shelves, and the spare shower to ensure everything meets our standards. Your input helps us improve, and we’re committed to making these updates promptly. We’re delighted you had a great stay overall and hope to welcome you back soon for an even better experience!
Verified review
6/10 Okay
Deborah C.
8 Dec 2025
Liked: Cleanliness
Disliked: Listing accuracy
Not misleading by being honest about listing. Listed as a beach home, & its a condo with 2 units. Listed making people believe you are able to enjoy the deck in the picture facing the beach, when instead, you are facing contractors busy drilling & pounding on a new condo. Not able to enjoy sitting on the deck at all, much less while looking at the ocean/beach. The place was clean, & was up about 20 steps to get in, which was not the biggest problem. The contractors also teased my dog, & caused her to bark more just coming out to go anywhere or go try to enjoy the beach, which was difficult. I feel like it was a grab to finish getting funds for my visit to fill the calendar, not my interest as a consumer. I wanted to just relax, sit on the deck, drink coffee, & look at the ocean, but that didn't happen. Not too impressed with no clear transparency regarding the condo, which is called a home on the listing. Nobody wants to come to the beach to listen to contractors drill, much less be looking directly at them if you go out to try to enjoy the deck on the rental.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 26 Dec 2025
Hi, Deborah, thank you for sharing your feedback. We are truly sorry that nearby construction on a neighboring property impacted your stay and prevented you from enjoying the deck as you had hoped. While this activity was outside of our control, we understand how disruptive it can be during a beach vacation and sincerely apologize for the inconvenience. The listing does describe the home as a duplex and notes it's a 3-minute walk to the beach. We understand how important clear expectations are when planning a stay and truly appreciate your feedback, which helps us continue refining our listing details for future guests. We are glad to hear the home itself was clean. Our guest services team completed a welcome call shortly after arrival, but we did not receive any communication or concerns during the stay. Had we been made aware, we would have been happy to assist in real time. We appreciate your feedback and wish you all the best moving forward.