Welcome to The Cottage on Pine!
On Anna Maria Island (Anna Maria, FL)
Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.
The Space
Step inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmosphere that feels both uplifting and serene. Located directly on Pine Avenue, this home offers the best of both worlds — walkable access to shops and cafés, and a peaceful retreat just beyond the gate.
Perfect for: Couples, small families, or friends seeking peaceful simplicity, walkable charm, and restorative island living.
Highlights
- Located on charming Pine Avenue, steps to boutiques, cafés, and beaches
- Private fenced backyard with heated pool, loungers, dining area, and outdoor shower
- Pet-friendly with prior approval and paid pet fee (up to two pets under 65 lbs)
- Open-concept living and dining area for gathering and connection
- Covered front porch perfect for morning coffee or evening reflection
- Professionally designed interiors blending modern comfort with coastal charm
Interior
- Living Area: Bright and welcoming with comfortable seating, Roku-equipped TV, and soft natural lighting that makes every moment feel unhurried.
- Dining Area: A table set for shared meals and conversation, perfectly placed between the living room and kitchen.
Bedrooms:
- King Bedroom: Features a king bed, TV, dresser, and French doors leading directly to the backyard and pool.
- Twin Bedroom: Two twin beds, TV, and ample storage — ideal for children or additional guests.
- Bathroom: Full bath with modern finishes, plush towels, and thoughtfully chosen amenities.
Each space reflects a sense of quiet care, from the crisp linens to the coastal textures and natural light that fills the home.
Layout Overview
Single-Level Living:
- Open-concept kitchen, dining, and living area
- One king bedroom and one twin bedroom
- Full bath
- Front porch and private fenced backyard with pool
This layout makes the home easily accessible for all ages and perfect for those who prefer simplicity and flow.
Outdoor Living
Step into your own private sanctuary.
The fenced backyard features a heated pool, loungers for sunbathing, and a shaded dining area for enjoying meals al fresco. An outdoor shower offers the perfect rinse after a beach day, while the grill invites slow, easy evenings spent under the island sky.
At the front, a covered porch with comfortable seating provides another peaceful perch — the ideal spot to enjoy Pine Avenue’s morning quiet or an evening breeze with your favorite drink in hand.
Kitchen & Dining
The kitchen blends charm and functionality, with premium Café appliances and everything you need to prepare fresh meals or quick snacks.
- Stove, oven, and microwave
- Refrigerator and freezer
- 12-cup coffeemaker, Keurig, blender, and toaster
- Fully stocked kitchenware for cooking and serving
Whether you’re creating a full breakfast before a beach day or reheating leftovers from one of Pine Avenue’s local eateries, this space makes it easy to feel at home.
Additional Amenities
- Washer and dryer (off covered porch)
- A/C and heat for year-round comfort
- Cable TV and wireless internet
- Hair dryer, iron, and ironing board
- Professionally laundered linens and towels
- Beach gear rental credit for items like chairs, umbrellas, and bikes
Parking
- Private driveway with space for 1–2 vehicles.
- Please note: The home is located behind another property that serves as our Once Upon A Beach office. All areas designated for guest use — including the private driveway, entrance, fenced backyard, and pool — are completely separate and exclusively yours, ensuring peace and privacy.
Write your vacation story at The Cottage on Pine — where calm meets connection, and every moment feels like coming home.
Policies
Policies updated October 6, 2025 — see full Terms & Conditions for details.
🔗 Cancellation Policy & Trip Insurance
🔗 Terms & Conditions
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.
- No Smoking
- Pets: Welcome with prior approval; maximum of two pets under 65 lbs each.
- Minimum Stay: Requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
- Primary guest must be 25+ and remain on-site for the duration of the stay
- Quiet Hours: 10 PM – 8 AM — please respect our island community
- Pool: Heated to 82–85°F year-round; temperature may vary with weather.
- Beach Gear: A rental credit is included with your stay; select items before arrival for delivery. Some gear may be on-site but is not guaranteed.
- Cleaning & Linens: Professionally cleaned between stays with starter supplies provided. Mid-stay cleans required for stays over 28 days.
- Golf Carts: Reserve through Once Upon A Beach Carts for an exclusive guest discount.
- Security: Exterior cameras monitor entry points and equipment for safety and occupancy compliance. Cameras do not face private areas.
- Accessibility: Single-level home; stairs not required.
Please Note
This home is conveniently located behind another property, which also serves as our office. Rest assured, all areas designated for this property—such as the private driveway, entrance, fenced-in backyard, and pool—are completely separate and exclusively for your use, ensuring a peaceful and private stay.
Max Occupancy: 5 Guests | Max Vehicles: 2
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
- Wifi
- Bed Linens
- Cable/satellite TV
- Dryer
- Hair Dryer
- Hangers
- Heating
- Internet
- Internet Access
- Iron
- Iron Board
- Linens
- Linens provided
- Living Room
- Parking
- Private Entrance
- Safety Card
- Self Check-In
- Smartlock
- Towels
- Towels provided
- TV
- Washer
- Bay
- Botanical Garden
- Coin Laundry
- Health Beauty Spa
- Marina
- Museums
- Playground
- Theme Parks
- Water Parks
- Zoo
- Not Necessary
- 24Hr Check-In
- All towels and bedding washed in hot water that's at least 60ºC
- Cleaning Disinfection
- Enhanced Cleaning Practices
- High-touch surfaces cleaned with disinfectant
- Self Check In / Check Out
- Emergency Exit Route
- Emergency Fire Contact
- Emergency Medical Contact
- Emergency Police Contact
- DVD player
- Laptop Friendly
- Satellite or Cable
- Television
- Newly Listed
- BBQ
- Coffee Maker
- Cooking Basics
- Dining Area
- Dining table
- Dishes Utensils
- Dishwasher
- Freezer
- Fridge
- Kettle
- Kitchen
- Microwave
- Oven
- Refrigerator
- Stove
- Toaster
- Wine glasses
- Antiquing
- Bird Watching
- Boating
- Bowling
- Eco Tourism
- Gambling
- Horse riding nearby
- Horseback Riding
- Miniature Golf
- Outlet Shopping
- Shopping
- Water Sports
- Wildlife Viewing
- ATM Bank
- Fitness Center
- Groceries
- Hospital
- Laundromat
- Beach
- Beach or lakeside relaxation
- Near Ocean
- Beach Access
- Garden Or Backyard
- Grill
- Outdoor seating
- Patio
- Private yard
- Heated Outdoor Pool Private
- Heated Pool
- Private Pool
- Carbon Monoxide Detector
- Deadbolt Lock
- Fire Extinguisher
- First Aid Kit
- Outdoor Lighting
- Smoke Detector
- Basketball Court
- Deepsea Fishing
- Fishing
- Fishing Bay
- Fishing Fly
- Fishing nearby
- Fishing Surf
- Golf
- Golf course within 30 min drive
- Jet Skiing
- Parasailing
- Pier Fishing
- Sailing
- Scuba or Snorkeling
- Skiing Water
- Snorkeling
- Snorkeling / Diving
- Surfing
- Swimming
- Tennis
- Tennis courts nearby
- Tubing Water
- Watersports nearby
- Wind Surfing
- Air Conditioning
- Central heating
- Children Welcome
- Free Parking
- Hot Water
- Minimum Age Limit
- Pets allowed
- Pets Considered
- Single Level Home
- Smoking Not Allowed
- Family
- Luxury
Want to know specifics? Ask anything about this specific property that you would like to know...
Example: "Is the balcony screened in?" or "Is there a toaster oven?"