PLAYGROUND’s Picks: Best Family Staycations

Tradewinds Island Resort, St. Pete

In the midst of this back-to-school craziness, Labor Day weekend is the perfect window to whisk your family away on a much-needed staycation! Orlando is rife with staycation hotspots, and there are even more gems lying in wait just a short drive from your doorstep. This year, the PLAYGROUND team is sharing their favorite Labor Day staycation spots with you!

Four Seasons Resort Orlando

Four Seasons Resort Orlando

Our ad team was unanimous: Four Seasons Resort Orlando at Disney World has some oh-so-exciting offerings, not to mention a delicious discount for locals!

“Every Labor Day, my family and I take a staycation at the Four Seasons Resort in Disney! We skip the parks altogether and just enjoy the gorgeous resort, pool, slides, kids club, lazy river, amazing restaurants and great service! They also offer a Florida resident rate during that time, so it makes it that much more enjoyable! We love this tradition and look forward to it every year! It’s a great way to kiss summer goodbye and say hello to the new school year!”   – Jessica Ventura, Advertising Manager


“We are planning to go back to Four Seasons. They offer a Florida resident discount, and the kids think it’s fun to staycation. They have a great pool, water slides, adult pool and lazy river… also, we can see Disney fireworks from the room!”   – Emily Weiss, Advertising Assistant

The Ritz Carlton, Amelia Island

Ritz Carlton Amelia Island

“Our family loves the Ritz Carlton Amelia Island. They always have great poolside activities for the kids, such as making terrariums, jewelry or other crafts. Each night, the staff leads a shark tooth hunt and will string your found teeth on a necklace. We also love the s’mores on the beach. Adults can enjoy a kid-free dinner, while the kids have a blast in the Kid’s Club. The Kid’s Club will feed them and engage them in activities for a set number of hours. Club level guests get this service free! Honestly, there’s so much to do and such great food that we never have to leave the resort.”   – Tracey Velt, Content Editor

St. Pete Beach

Guy Harvey Outpost

The pristine shoreline of St. Petersburg is another PLAYGROUND team fave! Between the relaxing resorts and aquatic activities, our publisher, Heather, and our online editor, Cortney, can’t get enough of this place.

“About two hours southwest of Orlando, St. Pete Beach has tons of oceanfront beach resorts to choose from, and many of them offer beachfront patios with live music- that’s the magic staycation ingredient for me. My family likes Bongos at the Grand Plaza Hotel (we even hosted our breezy, low-key wedding reception there!), but you can walk the strip of beach from Grand Plaza Hotel to the laid-back, surfer-style Postcard Inn and find plenty of live music and things to do along the way.

Almost every day, the TradeWinds Island Resort sets up an enormous inflatable slide on the beach and a water park in the Gulf (the kids make it look easy to climb on that thing; but trust me, it isn’t!). On our next staycation in St. Pete Beach, we’re going to try Swim with the Fishes at the Guy Harvey Outpost, where we’ll snorkel in a giant fish tank. This experience is for ages 8 and up, and it’s a cool way for younger kids to try out snorkeling for the first time.

We love this strip along St. Pete Beach because it’s the perfect combination of excitement for the kids and relaxation for the adults—the kids get their parasailing and paddleboards; I get my margaritas and live music. Perfect combination!”   – Cortney Thekan, Online Editor

Tradewinds Island Resort

“I recommend hitting St. Pete Beach to stay at TradeWinds Island Resort. It’s my favorite resort for families in that area. The water activities are a step above the other resorts with seven pools plus great sea play too — a ginormous inflatable water slide in the Gulf and a really cool inflatable surfing challenge. You can even sign up for “Tank Immersion” experience where families can go snorkel in an enormous fish tank. There are so many unique activities at this resort, I can’t imagine how you couldn’t have a good time.

PLAY Tip: Request a ground floor beach side suite with a patio near the pool. It allows for easier access for older kids to come and go while mom can easily keep an eye out from your room.

Bonus: Downtown St. Pete is the newest hot spot in Florida. Explore the plethora of restaurants, shops and museums in downtown. It’s like a little South Beach (Miami) but much closer to home.”   – Heather Reneau, Publisher


Have you found a new favorite staycation staple for your family? Tell us so on Facebook, and use #playorlando on your Instagram pictures to share the action with us!

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