Home in Anna Maria, Florida

🌅 Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | Tripletail Welcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay. Perfectly located just one block from Pine Avenue and the City Pier, this beautifully appointed 4-bedroom, 4-bath home offers the best of island living. Spend your mornings watching dolphins glide across the bay, your afternoons poolside, and your evenings soaking in the hot tub as the sky turns shades of pink and gold. 🏡 Comfortable Coastal Layout Designed for both gathering and privacy, Tripletail’s layout is ideal for families and couples traveling together: Main Level: King bedroom with waterfront access Second king bedroom Fully equipped kitchen, dining area, and family room with water views Upper Level: Two additional king bedrooms, each with private bathrooms Cozy sitting area perfect for reading, games, or relaxing after beach days With four king bedrooms and four bathrooms, every guest enjoys space, comfort, and convenience. ☀️ Waterfront Outdoor Living The magic of Tripletail truly unfolds outdoors: Private heated front-yard pool — perfect for relaxing on breezy or windy beach days Waterfront hot tub for sunset relaxation Spacious back deck with dolphin and boat-watching views Beach access just steps from the home Whether you’re sipping coffee at sunrise or unwinding with a cocktail at dusk, the bayfront setting provides a peaceful and picturesque backdrop. 🚲 Adventure & Island Exploring Your stay includes amenities designed for both land and sea adventures: Adult bikes for cruising charming island streets Paddle boards and kayak for exploring calm bay waters And with Pine Avenue just around the corner, you’re moments from boutique shopping, cafés, dining, and the historic City Pier. 🚗 Complimentary Golf Cart Included For effortless island transportation, Tripletail includes a complimentary 6-passenger street-legal golf cart with your reservation. Golf Cart Qualifications: Drivers must: Be age 25+ Sign a golf cart waiver Provide a valid North American driver’s license Provide proof of auto insurance International Guests: While we cannot provide a golf cart directly, we’re happy to connect you with our preferred partners offering exclusive guest discounts: Beach N Rides and Rentals The Coconut Rentals (premium gas golf carts) 💫 Why Guests Love Tripletail ✔ Bayfront hot tub + heated front-yard pool for flexible outdoor living ✔ Walkable to Pine Avenue, City Pier, shops & dining ✔ Four king bedrooms with private bathrooms ✔ Dolphin sightings right from your deck ✔ Included golf cart and adventure gear for easy island living Tripletail blends tranquility, walkability, and waterfront beauty — creating a stay guests return to year after year. 📌 Good to Know Amenity & Equipment Waiver required for all guests 18+ Pets welcome with pre-approval, fee, signed waiver & vaccination proof 24/7 guest support available for a seamless stay ✨ Hosted by Serendipity Vacation Rentals We look forward to welcoming you to your waterfront retreat at Tripletail.