ドックサイドデュオ-2つのサイドバイサイド2BR / 2BAウォーターフロントコンドミニアム

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.

We personally own and manage our vacation rentals, so 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!

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

In 2017, after touring several buildings, we purchased and renovated our first condo here, Dock of the Bay. Dockside won us over with its beautiful harbor setting and 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 couldn't pass up the opportunity. We purchased and renovated it, named it Dock Holiday, and suddenly had something pretty special: two complete waterfront condos side by side.

Today, guests can reserve both together as Dockside Duo—an ideal setup for two families, extended families, or four couples who want to vacation together while still having plenty of their own space and privacy.

And with so much of Clearwater Beach within walking distance, you can park the car—or skip the rental car altogether—and enjoy your vacation on foot.

What makes Dockside Duo truly unique is that you’re not simply renting a four-bedroom property—you’re getting TWO complete waterfront condos right next door to each other.

It’s an ideal setup for two families, extended families, or four couples who want to vacation together without giving up space and privacy. Between the two condos, you’ll enjoy four bedrooms, four full bathrooms, two full kitchens, two living rooms, two dining areas, two sleeper sofas, and two full-size washers and dryers.

The sleeping arrangements are especially comfortable for groups, with three KING bedrooms plus a fourth bedroom with TWO QUEEN beds, along with an additional twin bed and two sleeper sofas.

Both condos have been thoughtfully renovated and designed as comfortable, upscale coastal retreats. We’ve also tried to anticipate the little things that make group vacations easier, including well-stocked kitchens, beach wagons, chairs, umbrellas, coolers, and family-friendly extras.

Outside, enjoy the heated waterfront pool, sundeck, dock, gas grill, and picnic area overlooking the harbor. Watch the boats go by and keep an eye out for dolphins and manatees.

Best of all, you get a peaceful waterfront setting while being just a short walk from the beach, Pier 60, restaurants, shops, and entertainment.

Stay together, spread out, and enjoy the best of Clearwater Beach—all from two complete condos side by side.