Welcome to Decked Out!
On Anna Maria Island (Anna Maria, FL)
Where design meets ease and every detail invites you to slow down and savor the island rhythm.
Tucked just off Pine Avenue in the heart of Anna Maria, this artfully styled home blends the comfort of modern living with the character of the coast. Step inside and feel the calm — sunlight through French doors, the quiet hum of island life, and thoughtful touches that make it feel like it was created just for you.
Perfect for: couples who value design and downtime, small families seeking connection, or friends drawn to beautiful, meaningful spaces.
Highlights
- Central Anna Maria location — walkable to Pine Avenue shops and cafés
- Stylish open-concept living, dining, and kitchen space with Smart TV
- 2 bedrooms / 2 bathrooms including king suite with Sleep Number mattress
- Front and back decks for sunrise coffee or evening wine
- Private backyard with heated pool, cabana, and bar area
- Modern kitchen with granite countertops and stainless-steel appliances
- Washer/dryer, Smart TVs, and high-speed Wi-Fi
Interior Spaces
The interiors of Decked Out are inspired by clean lines, warm textures, and intentional comfort — a blend of Pottery Barn charm and island ease.
- King Suite: A tranquil retreat featuring a Sleep Number king bed, TV, and en-suite bath with a walk-in shower. French doors open to the front balcony — perfect for morning light or golden-hour sunsets.
- Queen Bedroom: Peaceful and welcoming with soft tones, a TV, and easy access to the shared bath featuring a shower/tub combination.
- Living Area: Light-filled with cozy seating, Smart TV, and seamless access to both front and back decks through French doors.
- Dining & Kitchen: A space where meals feel like moments. Granite counters, solid wood cabinetry, and stainless-steel appliances complement seating for four at the dining table and two at the breakfast island.
Every design choice — from the layered textures to the curated furnishings — has been selected with the Creator in mind: one who finds beauty in balance and inspiration in simplicity.
Layout Overview
- Elevated single-level home with front and rear decks
- Open living, dining, and kitchen concept
- Two bedrooms: one king with en-suite, one queen
- Two full bathrooms
- In-home laundry conveniently tucked in the pantry closet
The layout invites connection yet offers privacy — ideal for couples traveling together or a small family retreating to recharge.
Outdoor Living
- Out back, you'll find your private poolside sanctuary — lush, inviting, and designed for relaxed gatherings.
- Heated private pool (82–85°F; weather dependent)
- Brand-new cabana with outdoor bar and seating
- Gas grill for al fresco meals
- Loungers and shaded areas for sun or serenity
The fenced backyard feels like its own story: morning dips, lazy afternoons under the cabana, laughter over a shared meal as the string lights glow.
At the front, a second deck with seating offers another peaceful corner to enjoy the island breeze — proof that good design extends beyond the walls.
Kitchen & Dining
- Cooking here feels effortless — whether you're preparing a fresh catch or blending smoothies before a beach day.
- Full-size appliances: stove, oven, refrigerator with water & ice, dishwasher, and microwave
- Small appliances: coffeemaker (12-cup), blender, toaster
- Thoughtful extras: garbage disposal, quality cookware, and dishware
- Dining table for four plus breakfast island seating for two
Everything you need is within reach — a space built not just for function but for the joy of creating and sharing.
Additional Amenities
- Central A/C & heat
- Smart TVs & Wi-Fi
- Linens and towels provided
- Hair dryer, iron, and ironing board
- Washer and dryer in-unit
- Beach gear credit through VayKLife Gear — select chairs, umbrella, bikes, and more for delivery before arrival
Once Upon A Beach's local team ensures your experience is seamless — from arrival details to personalized recommendations.
Parking
- Driveway parking for 2 vehicles
- No garage access
At Decked Out, every space tells a story — one of ease, light, and intention.
Here, design becomes part of your memory.
The morning coffee. The laughter by the pool. The way the sunlight shifts across the deck as another island day unfolds.
Write Your Vacation Story.
Policies
NO SMOKING. NO PETS.
Booking & Fee Policy
Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.
Optional Services (subject to approval)
Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.
Reservations & Guest Requirements
Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.
Quiet Hours
10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.
Cleaning & Linens
Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.
Golf Cart Rentals
Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.
Pool & Spa
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.
Property Security
Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.
Payments & Cancellation Policy
Policies updated October 6, 2025 — see full Terms & Conditions for details.
Payment Schedule
Deposit
- Reservations up to 20 days: 50% of total amount due at time of booking.
Remaining Balance
- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.
Cancellation Policy
For Reservations of 20 Days or Less
- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.
- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.
- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.
- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.
Travel Insurance
CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.
Additional Terms
No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.
City of Anna Maria Vacation Rental License: VR16-000136
Max Occupancy: 4 Guests | Max Vehicles: 2
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
