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Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

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Sunny Side Down - Anna Maria Vacations
Sunny Side Down - Anna Maria Vacations
Sunny Side Down - Anna Maria Vacations
Sunny Side Down - Anna Maria Vacations
Sunny Side Down - Anna Maria Vacations

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6837 sq ft

Popular amenities

  • Parking available
  • Air conditioning
  • Pet-friendly
  • Dryer
  • Washer
  • Free WiFi

Explore the area

View in a map
Bradenton Beach, FL
  • Historic Bridge Street Pier
    ‪3 min drive‬
  • Cortez Beach
    ‪3 min drive‬
  • Coquina Beach
    ‪5 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Common Room

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Balcony

About this property

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

Sunny Side Down by Anna Maria Vacations
Bradenton Beach Beachside Retreat with Trolley and Beach Access
VRC16-000153

Welcome to Sunny Side Down, a colorful and cozy vacation rental perfect for families or small groups seeking a tranquil beach escape! Located just three minutes from Holmes Beach’s 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 in your outdoor oasis with beach gear, nearby water adventures, and easy access to island fun!

Highlights
• 3-minute walk to Cortez Beach
• 2 Bedroom / 2 Bath
• 1 King, 2 Twin Beds
• Trolley stops just minutes away
• Beach chairs and cart included
• Private washer and dryer
• Dog friendly (with prior approval and additional pet fee)
• Located near attractions like the Anna Maria City Pier, Bridge Street, and Pine Avenue
• 2 Parking Spaces

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

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 dining alfresco. The trolley stop, just steps away, makes it easy to hop on and explore all the island’s hotspots, including Bradenton Beach’s famous Pier, shops, and waterfront eateries. When you’re ready for adventure, rent watercraft, fish, or simply enjoy the island’s natural beauty.

Book Sunny Side Down today and enjoy a tranquil, fun-filled beach vacation in beautiful Bradenton Beach. Whether relaxing poolside, exploring local hotspots, or strolling to the beach, this cozy duplex promises lifelong memories!


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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.

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.

Property manager

Anna Maria Vacations
Premier Host

Languages

English

Add dates for prices

Amenities

Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
Parking available

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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

Pets allowed
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Smoking

Smoking is not permitted

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 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 Coquina Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Bradenton Beach, FL

What's nearby

  • Bradenton Beach Marina - 19 min walk - 1.6 km
  • Historic Bridge Street Pier - 3 min drive - 1.8 km
  • Cortez Beach - 3 min drive - 2.1 km
  • Manatee Public Beach - 4 min drive - 2.8 km
  • Coquina Beach - 5 min drive - 3.8 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive

Restaurants

  • ‪Anna Maria Oyster Bar on the Pier - ‬3 min drive
  • ‪Beach House Waterfront Restaurant - ‬18 min walk
  • ‪Daquiri Deck Bradenton Beach - ‬3 min drive
  • ‪Wicked Cantina - ‬14 min walk
  • ‪Tide Tables - ‬3 min drive

Frequently asked questions

Is Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!?

Check-in begins at 4:00 PM.

What time is check-out at Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!?

Checkout is at 10:00 AM.

Where is Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down! located?

Situated by the sea, this holiday home is steps away from Anna Maria Sound and Aluna Wellness Center & Spa. Bradenton Beach and Bradenton Beach Marina are also within 1 mile (2 km).

Reviews

9.8

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. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

8.0/10

Eco-friendliness

10/10

Check-in

10/10

Communication

9.0/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Esmeralda A.

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

Overnight Stay

Booked because of location close to the beach. Ended up loving the location, home & area. Will definitely be returning for a longer stay soon!
Stayed 1 night in Apr 2025

8/10 Good

Shelly C.

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

10/10 Excellent

Alexis A.

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

Perfect beach getaway

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

10/10 Excellent

Paul G.

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

nice

it was amazing. love the a/c. lol
Stayed 7 nights in May 2025

10/10 Excellent

Joanne V.

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

Great Location

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

10/10 Excellent

nilla k.

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

Perfect Location

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
Stayed 4 nights in Feb 2025

10/10 Excellent

Deborah E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Apr 2025

10/10 Excellent

Mchael D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Mar 2025

About the host

Hosted by Anna Maria Vacations

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests