ドックホリデー-ビューティフルウォーターフロント2BR / 2BAコンドミニアム

We fell in love with Clearwater Beach the same way many of our guests do—one vacation at a time!

Gary and I are originally from the Midwest, and once our kids headed off to college, we knew we wanted to escape the cold winters. After several visits to Clearwater Beach, we rented a condo here for a month in 2012. We loved it so much that one month became three the next year, then five the year after that. By then, we knew Clearwater Beach was where we wanted to be.

We eventually bought a home on North Clearwater Beach and now spend most of the year here.

Today, we personally own and manage Clearwater Beach Escapes, our small collection of waterfront vacation rentals. When you stay with us, you're communicating directly with the owners—not a large property management company. Because we live right here on the island, we're happy to share our favorite restaurants, activities, and local tips, and we're nearby if you need us.

We hope you'll fall in love with Clearwater Beach just as we did!

Kit & Gary

We chose Dockside because it offers the best of both worlds—a peaceful waterfront setting and an incredibly walkable Clearwater Beach location.

In 2017, we purchased and renovated our first condo here, Dock of the Bay, after touring several buildings in Clearwater Beach. Dockside won us over with its beautiful harbor setting and unbeatable location—just a five-minute walk to the sugar-white sand, with Pier 60, restaurants, shops, the marina, activities, and entertainment all within easy walking distance.

Guests loved Dock of the Bay, so when the condo right next door became available in 2019, we jumped at the opportunity. We purchased it, completed another major renovation, and Dock Holiday was born.

We love that guests can enjoy the quieter harbor side of Clearwater Beach while still being close enough to walk almost everywhere. You can park the car—or skip the rental car altogether—and enjoy your vacation on foot.

And because Dock Holiday and Dock of the Bay are side by side, larger families and groups can also reserve both together as Dockside Duo.

What makes Dock Holiday special is the combination of an upscale, thoughtfully designed condo, flexible sleeping arrangements, and a peaceful waterfront setting in the heart of Clearwater Beach.

After purchasing the condo in 2019, we completed a major renovation with the help of a professional carpenter and interior designer, creating a comfortable, upscale coastal retreat. With one KING bedroom and a second bedroom with TWO QUEEN beds, Dock Holiday is especially well suited for families, couples, and friends traveling together.

Step outside and the waterfront experience continues. The heated pool, sundeck, picnic area, and dock all overlook the harbor. Enjoy beautiful sunrises, watch the boats pass by, and keep an eye out for dolphins and manatees.

We’ve also tried to anticipate the little things that make a beach vacation easier—from a well-stocked kitchen and comfortable beds to beach chairs, umbrellas, a cooler, and a beach wagon ready for the short walk to the sand.

Best of all, you can enjoy a peaceful harbor setting while being just a short walk from the beach, Pier 60, restaurants, shops, and everything Clearwater Beach has to offer.