About Us

A family-owned collection of homes in Florida, Cape Cod, New Hampshire, and Costa Rica.

Get to Know Us

Our Story

Welcome to our Lucky vacation homes website. Lucky is our family nickname as our last name is Truluck-Williams and we truly feel Lucky in Life! This all came about as a result of us buying vacation homes in places that we love to stay, beginning back in 2004 with a cottage in Wolfeboro, NH on Lake Winnipesaukee and now encompasses three additional locations in Provincetown, Massachusetts; Sarasota, Florida and a beautiful pool home in Guanacaste, Costa Rica! Everything is family owned and operated! There’s me, Lucky (aka Dee), Jason, our two sons Storm and Ryne, and our little dog Sasha (10lbs of terror)! Also two grand daughters that you may meet too! We have so much fun meeting our guests. Sometimes just over the phone, or over a glass of wine, or dinner, or even a fun boat ride! Always happy to share all the local insight and best things to see wherever you are staying. Just ask away!

How We Live

Life on the Road

During the course of a year we stay at all of our places, having fun, doing renovations, upgrades, maintenance and reminiscing of all the fond memories of each place. We are truly Lucky in every sense of the word! You’ll typically find us in Venice and Sarasota , FL for the winter months, then Provincetown, MA on the tip of Cape Cod for the summer, at our lake house on Lake Winnipesaukee in the fall and then beautiful Costa Rica at different times throughout the year. Oh and we always take the annual trip to our native home in Wales where we stay with our other family in their vacation homes. Our life motto: Life’s short, Live long!

Paradise Found

Your Dream Beach Vacation Starts Here

Sarasota, Florida

Eight homes in Southside Village, a walk from twenty restaurants and bars and a short drive from the white sand of Siesta Key and Lido Key.

Provincetown, Massachusetts

Three rooms at the Dune Shack, five minutes on foot from Commercial Street and the nightlife, with Race Point and Herring Cove beaches beyond the dunes.

Wolfeboro, New Hampshire

A three bedroom waterfront cottage on Lake Winnipesaukee, with five kayaks, two canoes, a paddleboard and a sunfish sailboat waiting at the dock.

Junquillal, Costa Rica

A gated hideaway at Coco Loco Azul, with lush tropical gardens, an LED infinity pool and a wide sun deck a short hop from the Pacific coast.

What Sets Us Apart

Why Guests Come Back

Family-Owned Care

We own and stay in every home ourselves. The details matter to us because we're the ones who notice them.

Continuous renovations and upgrades
Personal attention to every detail
Real owners who know each property

Local Expertise

We know each destination from the inside. Ask us where to eat, what to skip, and what's worth the drive.

Insider tips for each destination
Genuine recommendations from experience
Happy to help over phone or in person

Four Distinct Locations

Four locations, each one chosen because we love it. Guests tend to come back to the same place year after year.

Lake Winnipesaukee, New Hampshire
Cape Cod, Massachusetts
Sarasota, Florida