Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach

We first visited the Florida Keys in 2009 — and it was love at first sight. The vibrant blue waters, laid-back island charm, and natural beauty captured our hearts in a way no other place had. That one trip sparked a dream: to not only put down roots here, but to create something we could share with others.

That dream became HappyintheKeys — a family-owned lifestyle brand and boutique collection of carefully curated, upscale vacation homes. What started with one home quickly grew into a small portfolio of unique, luxury residences designed for travelers who want more than just a place to stay — they want an experience.

Each of our properties reflects the spirit of the Keys: relaxing, welcoming, and full of coastal character. We take pride in thoughtful design, top-tier amenities, and the kind of attention to detail that turns a trip into a treasured memory. From the moment guests arrive, we want them to feel at home — and like they’ve discovered a slice of paradise they’ll never forget.

We're deeply involved in every home and every guest experience. When you stay at one of our HappyintheKeys properties, you’re not just booking a vacation rental — you’re joining a community of guests who return year after year for the comfort, quality, and care we’re known for.

We’re so glad you found us — and we can’t wait to share the Keys with you.

When we discovered this property, we immediately saw its potential — a rare, expansive lot with stunning water views, nestled at the end of a peaceful canal street. The land was perfect for creating unforgettable vacation experiences. But the home itself? Outdated, worn down, and in serious need of love.

So, we rolled up our sleeves and got to work. We stripped everything down to the studs and reimagined the entire space from the ground up. Every inch has been thoughtfully renovated to meet our highest standards — blending comfort, style, and functionality to create something truly special.

The result is Pirate Point: a fresh, modern retreat that honors the Keys' laid-back charm while delivering an elevated, luxurious experience. Whether you're gathering with family, reconnecting with friends, or simply escaping the everyday, this home is designed to help you unwind, recharge, and make memories that last a lifetime.

What makes Pirate Point truly stand out is its rare combination of privacy, space, and waterfront beauty — all wrapped in laid-back island luxury.

Tucked at the quiet end of a canal street, this property offers unmatched privacy and peace. With the home perched on a large corner lot surrounded by water on two sides, you're treated to expansive views of Coco Plum Bay and mangrove-lined canals — a constant connection to nature. Watch boats glide past from the windows and porches, or enjoy the soothing sway of palm trees from the hammocks at the corner of the grassy yard — a rare luxury in the Keys.

The outdoor space is a dream for both relaxation and recreation. There's plenty of decking and seating for sunbathing, dining, or sunset cocktails. The tiki hut with its cozy bench is a guest favorite — perfect for morning coffee, evening toasts, or watching dolphins and manatees pass by in the canal.

Families and groups love the thoughtful layout: large communal areas for gathering and celebration, plus quiet nooks where kids can play or adults can enjoy a moment of peace.

Fishing enthusiasts will love the extensive seawall — just grab a rod and cast off from your own backyard.

Pirate Point isn’t just a place to stay — it’s a destination. Whether you’re seeking fun-filled family adventures or peaceful tropical solitude, this home delivers a uniquely Florida Keys experience in every sense.