Seaside Vacation Rentals

STAY IN Seaside

Good For You

Sleeps 9 - Seaside

Kaleb 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

AmericanSeafood

$$$$

Amavida Coffee and Tea

American

$$$$

The Shrimp Shack

Seafood

$$$$

Airstream Row

AmericanBbqFrench

$$$$

Bud & Alley’s Pizza Bar + Trattoria

Italian

$$$$

Pickle’s Burger and Shake

American

$$$$

Great Southern Café

SeafoodSouthern

$$$$

Meltdown on 30A

American

$$$$

Black Bear Bread Co.

American

$$$$

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

W. Ruskin Access

Private To Specific Community

Natchez Private Access

Private To Specific Community

Savannah Access

Private To Specific Community

Coleman Beach Pavilion Access

Private To Specific Community

Seaside Pavilion Access

Private To Specific Community

Pensacola Private Access

Private To Specific Community

Odessa Private Access

Private To Specific Community

E. Ruskin Access

Private To Specific Community

Tupelo Access

Private To Specific Community

EVENTS OF Seaside

Wed, May 13

Live Music with DJ30A

Seaside

Live Music

Guests are invited to the Seaside Amphitheater in Seaside, Florida, for an evening of music featuring DJ30A from 6:00 PM to 8:00 PM. Attendees can grab a meal from the local Airstreams or a beverage at a nearby establishment before settling in for the performance. This complimentary outdoor event offers a lively atmosphere suitable for both dancing and relaxation.

Fri, May 15

Harrison Prentice

Seaside

Live Music

Harrison Prentice is scheduled to perform a live set from 4:00 PM to 7:00 PM.

Fri, May 15

Kylie Miller

Seaside

Live Music

Kylie Miller is scheduled to perform a live set from 4:00 PM to 7:00 PM.

Fri, May 15

Central Square Cinema: Paper Bear

Seaside

Family Fun

Families are encouraged to bring blankets and chairs to the Seaside Lyceum Lawn for outdoor movies under the stars. Screenings begin at 8:00 PM throughout May, weather permitting. The schedule includes Kung Fu Panda 4 on May 1, Bedtime Stories on May 3, Despicable Me 4 on May 8, Cloudy With A Chance of Meatballs on May 10, Paper Bear on May 15 and 24, The Game Plan on May 17, Spirit on May 22, The Garfield Movie on May 29, and Ratatouille on May 31.

Sun, May 17

Central Square Cinema: The Game Plan

Seaside

Family Fun

Families are invited to gather at the Seaside Lyceum Lawn with blankets and chairs for an outdoor movie experience starting at 8:00 PM, contingent on the weather. The May film schedule features Kung Fu Panda 4 on the 1st, Bedtime Stories on the 3rd, Despicable Me 4 on the 8th, and Cloudy With A Chance of Meatballs on the 10th. Later in the month, attendees can enjoy Paper Bear on the 15th and 24th, The Game Plan on the 17th, Spirit on the 22nd, The Garfield Movie on the 29th, and Ratatouille on the 31st. Movie reviews are available online to help families determine which screenings are appropriate for their needs.

Mon, May 18

Children’s Theater

Seaside

Arts & Culture

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 a complimentary event provided by the Merchants of Seaside through the Arts and Entertainment fee.

Wed, May 20

Live Music with DJ30A

Seaside

Live Music

DJ30A provides a musical performance from 6PM to 8PM at the Seaside Amphitheater in Florida. Guests are encouraged to grab food from the local Airstreams or drinks from nearby establishments before settling in for the evening. This free outdoor event offers a vibrant atmosphere suitable for both dancing and relaxation.

Fri, May 22

Emily Bass

Seaside

Live Music

Emily Bass will perform a live set from 4:00 PM to 7:00 PM.

Fri, May 22

Pre/Post Dinner Vibes – Live Music!

Seaside

Live Music

Attendees can experience a live performance by Jared Herzog between the hours of 4:00 PM and 7:00 PM.

Fri, May 22

Central Square Cinema: Spirit

Seaside

Family Fun

Families are invited to gather at the Seaside Lyceum Lawn for outdoor movie screenings under the stars. Starting at 8:00 PM, weather permitting, attendees can enjoy a variety of films throughout May, including Kung Fu Panda 4, Bedtime Stories, Despicable Me 4, Cloudy With A Chance of Meatballs, Paper Bear, The Game Plan, Spirit, The Garfield Movie, and Ratatouille. Guests are encouraged to bring blankets and chairs for a comfortable viewing experience.

Sun, May 24

Central Square Cinema: Paper Bear

Seaside

Family Fun

Mon, May 25

Children’s Theater

Seaside

Arts & Culture

Wed, May 27

Art Walk

Seaside

Live Music

Local merchants host a variety of artists, authors, and creatives as the community gathers to celebrate Art Month in Walton County. This initiative connects local businesses and organizations with the public to honor the visual, performing, and literary arts.

Wed, May 27

Live Music with DJ30A

Seaside

Live Music

Guests are invited to enjoy an evening of music featuring DJ30A from 6:00 PM to 8:00 PM at the Amphitheater in Seaside, Florida. Attendees can grab dinner from the Airstreams or visit a nearby restaurant for a drink before settling in to listen to the performance. This complimentary outdoor event provides a lively atmosphere suitable for both dancing and relaxation.

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

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

EASTER ON 30A: A PERFECT FAMILY GETAWAY

Easter on 30A is one of the most beautiful times of the year. Spring is in full swing, the Gulf is warming up, and the entire area comes alive with […]

Mar 17 Plan Your Trip

THE ONLY TIP NECESSARY FOR PLANNING A 30A VACATION?

Sure, planning a 30A summer vacation sounds easy. Then the options start multiplying. One house has a private pool. Another is closer to the beach. Someone insists on Seaside. Someone […]

Mar 16 Plan Your Trip

Nov 27 2024