DECKED OUT - Stunning Luxury Home! Huge Sunny Private Pool, Block to Pine 8 Min Walk to Beach

neighborhood of Anna Maria Vacation Rentals
  • Sleeps 4
  • 2 Bedrooms
  • 2 Bathrooms
  • 1250 sqft.


Welcome to Decked Out!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.A gorgeous home filled with luxurious furnishings, high-end touches, and smart home technology! The home is picture perfect from a Pottery Barn or Restoration Hardware magazine and couldn't be in a more perfect location! Located just a block to Pine Avenue shops, the free island trolley stop, Waterfront Restaurant, and close to the bay side beach and park. But because the island is narrow the gulf side beach is only a 6-8 minute walk directly down the opposite end of the street! This is one of the most sought after areas of the island to stay and for good reason as the bay is perfect f...

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  • Balcony
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Outdoor Furniture
  • Porch / Veranda
  • Books
  • Satellite / Cable
  • Stereo
  • Toys
  • TV
  • Air Conditioning
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Internet
  • Living Room
  • Parking
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Pool
  • Private Pool
  • Children welcome
  • Luxury
  • Activities / Restaurants Guide
  • Beach Umbrellas
  • Cooking Utensils
  • Dining Area
  • Freezer
  • Keyless Entry System
  • Lanai / Gazebo
  • Outdoor Gas Grill
  • Terrace / Balcony

Location Info

This little town at the northern tip of Anna Maria Island—full-time population 1,800—is beloved for its beachy ambiance, but it isn’t stuck in time. In the last decade, investors have snapped up many humble 1960s-era concrete-block residences and built multi-story mega vacation rental homes in their place. Now, nearly 70 percent of homeowners are rental owners. That means a constant turnover of weeklong visitors, who bicycle or ride their golf carts to scenic Pine Avenue to shop, dine and stroll to the Anna Maria City Pier and the Rod ’N Reel Pier, with their knockout views of the Sunshine Skyway bridge. Venerable institutions like the Island Players community theater, a weekly farmers market, and the Studio at Gulf and Pine art gallery, which its variety of hands-on art classes, help create a sense of community.


Nightly rates range from $255.00 to $750.00


About Owner

We are Mike & Nikki Kaleta with Once Upon A Beach Vacation Rentals & Property Management, full-time island residents, and a husband and wife team who solely own and operate our boutique luxury vacation rental agency on Anna Maria Island, Florida. We currently manage 30+ throughout the island on behalf of our owners. We relocated here in 2016 after we fell in love with the small town feel of this beach island paradise and built our small business from the ground up with the passion to share this beloved island with others. It is our utmost goal to make every one of our guests instantly feel at home as a 'true local' in one of our unique, pristine, meticulously designed and luxurious accommodations. From small beachside bungalows to sprawling...

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Check-In Time : Flexible
Check-Out Time : Flexible
  • Suitable for Children

General Policies


Max Occupancy: 4

Max Cars: 2
City of Anna Maria: VR16-000136

The information provided online, though deemed accurate is not guaranteed. It is subject to errors, omissions, change of price or withdrawal without notice.

House Rules

Registered Guest must provide copy of ID, be at least 25 years of age and be present throughout entire stay.  *Beach Gear Equipment (Provided by VayKLife Gear): Assorted beach gear items may be onsite but not guaranteed. Every reservation now includes a credit towards personalized beach gear rental included with your stay (chairs, cart, umbrella, bikes, coolers, games, and so much more). Simply make selections prior to your stay and we will have at your home for you!Standard occupancy is 2 persons per every standard bedroom, an additional occupant fee of $25 per person/per night will be assessed for each occupant over this up to max occupancy, if applicable.Quiet Hours 10p-8a. You are vacationing in a residential area. Please be a goo...

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Terms & Conditions

Cancellation Policy

CANCELLATION POLICY: Please review the details of our Cancellation Policy page or Terms & Conditions at booking. We encourage you to review as OUR POLICIES HAVE CHANGED as of MARCH 25, 2023. We continue to offer refunds of deposits for cancellations (for stays of 28 days or less) made greater than 60 days to arrival, however all cancellations are now subject to a non-refundable booking admin fee. We continue to offer our US Citizens guests (with exception to residents of NY and HI) the option of purchasing CSA Travel Insurance directly with us. We strongly encourage all guests to purchase Travel Insurance in the event of any unforeseen eventualities. Refunds or credits are not provided for COVID-19 related cancellations, weather...

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(Based on 17 reviews)
- 01/01/2022 -

Visit in January

"It was great! Clean, great location and easy to work with the owners!"

- 01/01/2022 -

Perfect getaway!

"The property was very nice! Backyard is like an oasis. Location was great! Easy walking distance to beach and Pine street. We would stay again!"

Host Reply
Thank you so much, Kathy! We love Decked Out's backyard too! We'd love to host you again in the future and thank you for choosing Once Upon A Beach!
- 01/01/2022 -

Boutique Oasis

"What a wonderful stay!! Perfect location, a close walk to cocktails and dining options, Pine Street and, to the beautiful beach! The home was very clean, has a well stocked kitchen, new appliances, and a lovely outside pool and gazebo area. An absolute MUST for us to return and stay again at this wonderful property on beautiful AMI !"

Host Reply
Thank you, Bonnie! We thoroughly loved having you and your guests! We are so happy to hear how much you enjoyed Decked Out. We'd love to host you again in the future and thank you for choosing Once Upon A Beach!
- 12/01/2021 -


"Very late with are review, we stayed during the Christmas break WoW loved the island loved the accommodation it’s the only holiday we take in the year and it’s mid February and family still missing it worth every penny/dollar. Accomadation was great if you young kids take them there great family time pool was great after a hot day at the beach. To many great things to say about the accommodation. To list the island to is great"

- 12/01/2021 -

Great location

"As close to the ocean as you can get without paying waterfront prices. Clean, modern, well-equipped home with a well landscaped pool area. The heated pool is a plus (not all homes on the island have heat for their pools). SHORT walk to shops, with the Waterfront restaurant being steps away. Will definitely rent again."

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