Seaside Vacation Rentals

STAY IN Seaside

Son Worshipers

Sleeps 8 - Seaside

Madi Grayton

View All Homes On 30A

About Seaside

The Birthplace of New Urbanism. Why was The Truman Show filmed here? And why did Newsweek call Seaside “the most influential resort community since Versailles”?

Seaside put New Urbanism on the map, but life here is surprisingly normal. There’s a market, post office, bookstore, record shop, and art galleries… mixed with cozy cafes, 4-star restaurants, and locally-owned boutiques. And with a weekly farmers’ market, live outoor concerts, and starlit movie nights, the fun never slows.

Once you first lay eyes on this Gulf-front paradise, you’ll see why Seaside is truly in a league of its own. With nine unique beach pavilions (each designed by a different architect!), cobblestone streets, adorable cottages, and walkable, timeless neighborhoods, this dreamy spot feels both classic and current.

WANDER HERE, DINE THERE.

Smack dab in the middle of it all, Seaside feels like the unofficial headquarters of 30A. Sandwiched between WaterColor and Seagrove, there’s no denying it’s a prime spot for dining, snacking, shopping, and laid-back fun. With its walkable streets, everything’s within flip-flop reach, so come on over and feel the buzz.

PICKET FENCES.

Founded in the 1980s, Seaside was the birthplace of New Urbanism, designed as a walkable, close-knit community, that encourages neighborly interaction. Its colorful homes, picket fences, and iconic front porches are now recognized worldwide, even making an appearance in the film The Truman Show.

CATCH THE BUZZ.

This isn’t your typical coastal vibe. Sure, it’s laid-back, where slowing down and soaking it all in is the rule of the day. But there’s something more here. The dazzling neighborhood vibrates with live music, art festivals, and local gatherings all year long. And with a cozy bookstore, a cool record store, and Airstream Row, an adorable food truck hub, It’s more than just a coastal scene- it’s a little slice of beachside cool. You dig?

SCENERY, SERENITY, OH SO NICE.

Seaside has snagged the title of “No. 1 Beach in the World for Families” from Travel & Leisure Magazine, and it’s easy to see why. But the praise for Seaside doesn’t stop with its small-town charm and world-class accommodations. Its natural beauty is the real hero here (those sunsets from the beach!). With native plants thriving throughout, upscale living and gorgeous landscapes live hand in hand. Lovely.

Bud & Alley’s Pizza Bar + Trattoria

Italian

$$$$

Meltdown on 30A

American

$$$$

Great Southern Café

SeafoodSouthern

$$$$

Pickle’s Burger and Shake

American

$$$$

Amavida Coffee and Tea

American

$$$$

Black Bear Bread Co.

American

$$$$

The Shrimp Shack

Seafood

$$$$

Bud & Alley’s

AmericanSeafood

$$$$

Airstream Row

AmericanBbqFrench

$$$$

Dining near Seaside vacation rentals offers a range of gourmet restaurants, casual eateries, and charming cafes. Enjoy fresh seafood, farm-to-table dishes, and international cuisine at popular spots like Bud & Alley’s, Great Southern Cafe, and Amavida Coffee. Savor oceanfront dining with Gulf views or grab a quick bite at the vibrant food trucks on Airstream Row. For a romantic dinner or a family-friendly meal, Seaside provides!

Seaside BEACH ACCESSES

E. Ruskin Access

Private To Specific Community

Natchez Private Access

Private To Specific Community

Odessa Private Access

Private To Specific Community

Coleman Beach Pavilion Access

Private To Specific Community

Pensacola Private Access

Private To Specific Community

Seaside Pavilion Access

Private To Specific Community

Tupelo Access

Private To Specific Community

W. Ruskin Access

Private To Specific Community

Savannah Access

Private To Specific Community

EVENTS OF Seaside

Tue, June 9

Farmer's Market

Seaside

Markets & Shopping

The Seaside Farmers Market is held at the Seaside Amphitheater every Saturday from 9 AM to 1 PM, with additional Tuesday hours during June and July. Located near Airstream Row, the market features local growers and artisans providing healthy, environmentally conscious products such as fresh produce, specialty items, artisan cheeses, and breads. The event serves as a community hub offering cooking demonstrations, seed exchanges, and educational opportunities focused on sustainable living. Beyond the market, the area hosts a variety of family-friendly activities, including yoga, outdoor movies, and live performances throughout the year.

Wed, June 10

Live Music with DJ30A

Seaside

Live Music

Guests can enjoy an evening of music featuring DJ30A from 6 PM to 8 PM at the Amphitheater in Seaside, Florida. Attendees are encouraged to grab dinner from the local Airstreams or have a drink at a nearby establishment before settling in to enjoy the performance. This free outdoor event offers a lively atmosphere suitable for both dancing and relaxing.

Fri, June 12

Jared Herzog

Seaside

Live Music

Jared Herzog performs a live musical set from 4:00 PM to 7:00 PM.

Fri, June 12

Zack Miller

Seaside

Live Music

Zack Miller will be performing live from 4:00 PM to 7:00 PM.

Mon, June 15

Children’s Theater

Seaside

Arts & Culture

Emerald Coast Theatre Company presents a family-friendly version of William Shakespeare’s A Midsummer Night’s Dream at the SEASIDE® Amphitheater. This production offers a magical and humorous experience for audiences of all ages in Central Square. The performance is complimentary, funded by the Arts & Entertainment fee collected by the Merchants of Seaside.

Tue, June 16

Farmer's Market

Seaside

Markets & Shopping

The Seaside Farmers Market is held in the Seaside Amphitheater every Saturday from 9 AM to 1 PM, with additional Tuesday markets during the same hours from June through July 30. Located adjacent to Airstream Row, the market is surrounded by various shops and restaurants. This producer-focused market features local growers and artisans offering healthy, environmentally conscious products, including fresh produce, specialty items, artisan cheeses, and breads. Visitors can also enjoy cooking demonstrations, educational sessions on food preparation, and seed exchanges. Seaside serves as a family-friendly destination that hosts a variety of year-round activities, such as morning yoga, outdoor movies, children's theatre, and sunset concerts.

Wed, June 17

Live Music with DJ30A

Seaside

Live Music

Fri, June 19

Harrison Prentice

Seaside

Live Music

Harrison Prentice will perform a live musical set from 4:00 PM to 7:00 PM.

Fri, June 19

Jared Herzog

Seaside

Live Music

Jared Herzog will be performing live from 4:00 PM to 7:00 PM.

Mon, June 22

Children’s Theater

Seaside

Outdoor Activities

Emerald Coast Theatre Company presents a family-friendly adaptation of Shakespeare's A Midsummer Night’s Dream at the SEASIDE Amphitheater. This enchanting production brings magic, mischief, and romance to Central Square, offering a joyful experience for audiences of all ages. The performance is complimentary and supported by the Arts and Entertainment fee collected by the Merchants of Seaside.

Tue, June 23

Farmer's Market

Seaside

Markets & Shopping

The Seaside Farmers Market is held at the Seaside Amphitheater every Saturday from 9 AM to 1 PM, with Tuesday hours added from June through July. This producer-led market features local growers and artisans offering healthy, environmentally conscious food, produce, and handmade goods. Located near Airstream Row, the market provides a family-friendly atmosphere with educational demonstrations and community events that celebrate local ingredients and sustainable living.

Wed, June 24

Live Music with DJ30A

Seaside

Live Music

Seaside guests can enjoy an evening of music featuring DJ30A from 6 PM to 8 PM at the Amphitheater in Seaside, Florida. Attendees are encouraged to pick up dinner from the local Airstreams or visit nearby bars and restaurants for a drink before relaxing to the music. This complimentary event offers a lively atmosphere suitable for both dancing and unwinding.

Expect wonderful year-round events that draw curious visitors, including the Farmers Market every Monday and Saturday. Enjoy live music at Sounds of Seaside, and don’t miss the Seeing Red Wine Festival in the fall. Holiday events feature the Christmas Parade and New Year’s Eve fireworks. Art lovers can visit the First Friday Art Walk, and athletes can join the Half Marathon and 5K Run in the spring. These events make this adorable town a vibrant destination year-round.

Seaside STORIES

SEAGROVE VS. SEASIDE: WHICH 30A COMMUNITY FITS YOUR TRAVEL STYLE?

30A isn’t a one-size-fits-all coastline. Where you stay quietly sets the tone for the entire trip. Some communities lean quiet and residential. Others lean social and center-stage. Picking the right […]

Jan 27 Area Highlights

SLOW MORNINGS IN SEASIDE: COFFEE SHOPS, BOOK BROWSING, & GULF VIEWS

Mornings in Seaside have their own kind of magic. Streets stretch awake, sunlight spills like a soft brushstroke, and the smell of salt lingers in the breeze. A morning here […]

Dec 25 Area Highlights

EVENING VIBES: BEST SUNSETS, NIGHT WALKS, AND COASTAL STARS

When beach towels head home and the sky starts to blush, the coast finds a new kind of magic. Quieter. Softer. The kind that makes you talk slower and smile […]

Nov 03 Area Highlights

TREAT TRAIL: ICE CREAM, DONUTS & SWEET SHOPS IN SEASIDE

A SWEET STROLL THROUGH SEASIDE Seaside is already known for its delightful cottages, walkable streets, and beach-town charm. But if you’ve got a sweet tooth, it’s also home to one […]

Aug 20 Area Highlights

SEASIDE SMILES: YOUR GUIDE TO FAMILY-FRIENDLY FUN ON 30A

Sunshine, sugar-white sand, and a town where laughter fills the air like the scent of saltwater. Seaside, Florida, a gem on 30A’s crown, is calling your family’s name! More than […]

Mar 27 Area Highlights

EXPERIENCE SEASIDE: THE HEART OF 30A AND THE BIRTHPLACE OF NEW URBANISM

A GULF-FRONT GEM WITH GLOBAL FAME Seaside isn’t just another beach town, it’s a carefully crafted community that changed the way coastal towns are designed. With pastel cottages, white picket […]

Mar 07 Area Highlights

SEASIDE’S ANNUAL EVENTS. A YEAR-ROUND CELEBRATION!

Seaside. A beautiful beach town along 30A, it’s also a nonstop playground of fun, flavor, and festivities, January through December! From toe-tapping tunes to dachshund derbies, every season brings something […]

Jan 27 Area Highlights

KIDS, SAND, AND POOLS.

Morning is pure magic. A kid sprints full speed at the waves, a couple more are building a sand city that’s “not finished yet.” And look at you… all proud, […]

May 31 Plan Your Trip

30A BEACH CHAIR SERVICE: ABSOLUTELY DREAMY

Just say no. No balancing chairs with one arm while dragging a cooler with the other. No lugging fifty pounds of “beach essentials” through soft sand. And no umbrella that […]

May 26 Plan Your Trip

FOURTH OF JULY ON 30A, FLORIDA (2026 GUIDE)

The chaotic ‘sunrise’ parade in Grayton Beach smells like sunscreen before 8 am. And later on in Panama City Beach, the Gulf’s biggest fireworks are to blame for sore necks […]

May 11 Plan Your Trip

THE HIDDEN COSTS OF A 30A VACATION (AND HOW TO PLAN SMARTER)

“That $450-a-night beach house is perfect!” But when you click through to book, the total number is way higher than you expected. This catches a lot of people off guard. […]

Mar 20 Plan Your Trip

Nov 27 2024