The Court
The Court is Seaside’s only boutique hotel. The Court, formally known as the Motorcourt, has been remodeled from top to bottom with stunning exteriors and beautifully decorated with Serena &…
An Experience for Every Season
Your perfect escape is closer than you think. This season, Seaside welcomes you to slow down and savor a simple, beautiful life. Come with friends for sun-soaked gatherings, make it romantic for a postcard-worthy escape, or bring the whole family for memories that linger long after the sun sets. However you arrive, you’ll discover a sense of ease and a reminder that the best moments are the simplest ones. Trade city life for southern living, deep dish for coastal delights, and the lakefront for white sand and turquoise waters—all in Seaside, Florida.
Welcome, Chicago!
From the Windy City to the Gulf Coast, Seaside invites you to experience an escape where simplicity wins, memories last and your story is waiting to be written. Perched along Florida’s Scenic Highway 30A, this is the birthplace of New Urbanism—a town planned for walking, biking, and connecting. Think pastel cottages, brick-paved streets, and a town square straight out of a movie set, all layered with a 45 year history defining the art of living.
Seaside set the tone for coastal living on 30A, as the first of its kind with intentional design, community, and charm across the coast.
The town feels instantly familiar yet refreshingly different. It’s the kind of place where you can enjoy luxury at your leisure. Rent a bike and hop between towns, admire the pristine nature and rare dune lakes, or simply plant yourself on beaches that consistently rank among the world’s best. If you love weekend escapes by the water, 30A is the natural upgrade. The sand is so pure, thanks to its quartz composition washed down from the Appalachians over millennia, that it’s even known to squeak under bare feet.
Seaside is quaint and effortlessly stylish in a way that feels warm and welcoming — perfect for Chicagoans who want to unplug without losing that sense of community.
Luxury at Your Leisure
Dine
Dine
In Seaside your favorite restaurant is always just a walk away.
Stroll to any of the local restaurants, eat fresh seafood by the Gulf, and take in the flavors and soothing rhythm of life.
Shop
Shop
Shopping in Seaside blends coastal charm with curated style, offering everything from locally owned boutiques and beach-ready fashions to whimsical gifts and timeless treasures, all within a walkable, picturesque town square.
Play
Play
Immerse yourself in the lively atmosphere of Seaside, where the bustling energy of our community events transforms ordinary moments into cherished memories.
Stay
Stay
Enjoy a weekend getaway at our boutique hotel. Or stay for the week with your families and friends in one of the charming cottages and homes offered by our rental partners.
What to Expect: Midwest Meets Gulf Coast
Picture-perfect Weather: Winters are mild, springs are breezy, and summers linger warm and golden.
Laid-Back Luxury: World-class design with a refreshingly casual vibe. Shorts, sundresses, or linen feels right everywhere.
Community Spirit: Festivals, concerts, and family gatherings are the heartbeat of Seaside. Think Midwest warmth with a splash of sun and salt air.
Culinary Coast Meets Chicago Taste
Chicagoans know food, and Seaside delivers. From shrimp straight off the boat to fine dining with Gulf views, the town has earned its reputation as a culinary hub. The highlight? The Seeing Red Wine Festival, now over 30 years strong and named one of Fodor’s “Top 10 Can’t Miss Fall Wine Festivals.” Pair that with farmers markets, seasonal culinary delights, and airstream food trucks, and you’ll never go hungry.
The only thing better than the food is the view
A Year-Round Calendar of Events
Seaside doesn’t take a season off.
Spring: Outdoor movies, children’s theater, and concerts under the stars.
Summer: Fireworks, festivals, and bustling markets.
Fall: The legendary Seeing Red Wine Festival and the iconic Halloweener Derby.
Holidays: The town transforms with parades, Santa sightings, and a coastal spin on winter wonderland.
Getting Here: Easier Than You Think
Flights: United, American, and Southwest all offer nonstops from O’Hare (ORD) and Midway (MDW) to Northwest Florida Beaches International Airport (ECP)—just 30 miles from Seaside. Additionally, Destin-Ft Walton Beach (VPS) is ~40 miles away and Pensacola (PNS) is ~75 miles.
Time: In under three hours, you can trade the Magnificent Mile for miles of sugar-white sand.
On the Ground: Rental cars and private shuttles make the short ride simple.
Pro tip: pack light, live simply.
Stay Awhile
Seaside offers accommodations for every kind of traveler, whether you want Gulf-front luxury, a quaint cottage or a cozy room for 2. Staying in Seaside brings a one-of-a-kind experience that lets you live like a local, just steps from the water.
Homeowner’s Collection
Homeowner’s Collection Vacation Rentals is Seaside, Florida’s largest vacation rental company, with over 190 private homes in its portfolio. Established in 2012, we are owned by our participating cottage homeowners…
Beaches
The beaches of SEASIDE® are where the sugar-white sand meets the crystal-clear waters of the Gulf. Nestled along Florida’s famed Emerald Coast, our shoreline is known for its natural beauty,…
Plan Your Escape
Chicago → Seaside
Nonstop flights in under 3 hours
30 minutes from the airport
Ready to make Seaside your second city escape?
Book Your Stay
Explore Weddings & Group Options
Join Us for Seeing Red Wine Festival
Stay Connected.
Follow @seasidefl on Instagram.
