Large Homes Curated for Connection

A Shore Thing was made for together time — shared meals, poolside afternoons, and sunset views from the rooftop deck. Whether you’re reuniting with family or vacationing with friends, this home welcomes gathering with ease and care in every detail.

Step into Three Little Birds — a bright, joyful island home designed for gathering, connecting, and letting the days unfold naturally. With Gulf views, a private heated pool and spa, and spacious living areas made for shared laughter, this home captures the spirit of Anna Maria Island living.

A Wave From It All — a single-level island home crafted for connection and carefree living. Tucked on the quiet north end of Anna Maria Island, this pet-friendly retreat offers open living spaces, a private backyard oasis, and all the comforts you need to gather with family and friends.

At Mariner’s Crossing, every space is designed for connection — morning coffee shared on a balcony, kids’ laughter echoing from the pool, family dinners that stretch into evening stories. Here, the moments between adventure and rest become the ones you’ll remember most.

Every corner of this home is designed to bring people together. Write your vacation story at Sunsets on Carissa, where every sunset calls you back to what matters most — time together.

With its inviting design, central location, and easy access to the island’s most beloved beaches, Sol Mate offers the perfect setting to gather, reconnect, and write your next chapter on Anna Maria Island.

Cozy Cabana West offers the kind of calm that stays with you — where the pace slows, the light softens, and your story begins to feel a little more like home; slow mornings and quiet evenings meet the rhythm of island life.

Step into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike paths, and the soft hum of island life—this pet-friendly home blends vintage character with thoughtful updates

At Tern Key, every detail — from the soft ripple of the water to the glow of the evening sky — was designed to inspire connection and creativity. Whether you’re here to gather, celebrate, or simply breathe in the island air, this home offers the space and intention to make it meaningful.

Where connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island living. Nestled along a peaceful canal with direct access to the Bay and Gulf, this home blends modern elegance with warm hospitality

Family Tides — Where gathering comes naturally and every generation finds its place in the sun. Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers space to spread out, come together, and share the kind of moments that become family legend — poolside laughter, sunset toasts on the rooftop, late-night stories told under the stars.

Experience Bateman’s — where thoughtful design and waterfront living come together. Set along a quiet canal on Anna Maria Island’s north end, this modern coastal home blends refined interiors with inviting outdoor spaces made for gathering, relaxing, and enjoying the island’s natural beauty.

Where Connection Feels Like Home 🌴

Spread out blankets and unpack local eats as the sky fades to gold. Watch the colors shift, share stories, and let the sound of the waves carry your laughter.

Try: Poppo’s Taqueria (212C Pine Avenue, Anna Maria) for handheld tacos and bowls made with fresh, local ingredients, or The Feast  (5406 Marina Drive, Holmes Beach) for easy takeout options like flatbreads, charcuterie, and a great wine list.

Where:

Bean Point (north end of Anna Maria Island — at the intersection of North Bay Blvd. and North Shore Dr.)offers a peaceful, tucked-away stretch of sand where you can watch the sun melt into the Gulf with fewer crowds.

Coquina Beach (south end of the island, 2650 Gulf Dr. S., Bradenton Beach) features wide sands, amenities like picnic tables and restrooms, and a lively atmosphere with local vendors and music nearby.

Trade beach sandals for putters and spend the evening in friendly competition under twinkling lights. The Fish Hole Mini Golf is one of Anna Maria Island’s most charming spots to gather — surrounded by tropical landscaping, koi ponds, and the easy laughter that comes with a little lighthearted rivalry. It’s the perfect mix of nostalgia and island fun, whether you’re playing with kids, friends, or just those who feel like family.

Try: Cool off afterward with homemade ice cream or shaved ice from Two Scoops just around the corner — a local favorite for post-game treats.

Where: The Fish Hole Mini Golf, 115 Bridge Street, Bradenton Beach, located near the historic Bridge Street Pier. There’s plenty of shopping, dining, and live music nearby — making it easy to turn one game into a whole evening out together.

Whether you love to cook together or prefer to sit back and be served, the island makes it easy to enjoy food as connection.

Try: Chef Mike offers private, in-home dining experiences tailored to your taste and schedule. From coastal-inspired small plates to multi-course dinners, he brings restaurant-quality cuisine right to your vacation home — no grocery run required. 

Or Visit: The Island Fresh Market (5604 Marina Drive, Holmes Beach) for local seafood, produce, and ready-to-grill favorites. It’s the perfect stop for snapper, shrimp, or freshly prepared sides to enjoy by the pool.

Light the candles, pour something chilled, and let the conversation stretch long into the night — because the best meals aren’t just about the food; they’re about the moments you make around the table.

Ease into the day the island way — toes in the sand, coffee in hand, and little hands shaping towers between tides. These are the slow, golden mornings that make time feel endless. 

Try: North Shore Café (304 Pine Avenue, Anna Maria) — a cozy, open-air café loved for its cold brew, smoothies, avocado toast, and warm island hospitality. Grab your coffee and breakfast to go, or linger in the garden before heading to the beach.

Where:

Bean Point (north end of Anna Maria Island — where North Bay Blvd. meets North Shore Dr.) offers a peaceful, scenic stretch of sand with stunning views of the Gulf meeting Tampa Bay — perfect for a quiet morning of sandcastles and serenity.

White Avenue Beach Access (between 80th and 81st Streets in Holmes Beach) is a tucked-away gem with gentle waves, easy parking, and space for little ones to play without crowds.

Bring buckets, laughter, and no agenda — just the joy of starting the day with salt on your skin and memories already in the making.

Pack the cooler, grab your crew, and head out for a day on the water — where laughter carries on the breeze and every wave feels like an invitation to explore. Drift past dolphins, drop anchor at a sandbar, or simply float under the sun and let the island show you her quieter side. These are the days that turn into the stories everyone remembers.

Try: Anna Maria Charters with Captain Laura — known for her warm hospitality, local knowledge, and family-friendly approach to exploring the island by water. From dolphin cruises and sandbar picnics to sunset charters, Captain Laura crafts each trip to match your group’s pace and personality.

Bring your favorite snacks, sunscreen, and sense of adventure — the rest is handled by the sea, the sunshine, and a captain who knows just where to find the magic.

When the table is set and laughter drifts through the air, the Gatherer comes alive —  not to plan, but to share.

On Anna Maria Island, connection feels effortless — it happens between tides and twilight, across porches and pool decks, wherever warmth and welcome meet. Every shared meal, every sunset toast, every burst of laughter becomes part of a memory stitched together by the people who make it matter most.

Maybe tomorrow tells a different kind of story — and that’s the beauty of this place. 🌅

Today you’re the Gatherer, surrounded by those who make life full… but perhaps next time you’ll be: