Seaside Vacation Rentals

STAY IN Seaside

Good For You

Sleeps 9 - Seaside

Madi Grayton

View All Homes On 30A

About Seaside

Walkable before walkable was cool. Construction began in Seaside in 1981, helping launch the New Urbanism movement with a simple idea: build a town where people actually want to walk, gather, and know their neighbors. Then The Truman Show came along and turned Seaside into a movie set, too. 40-plus years later, people are still walking.

THE CENTER OF THE UNIVERSE. SORT OF.

Seaside’s social life revolves around Central Square, where you’ll find cafés, shops, galleries, and longtime favorites like Sundog Books and Central Square Records. Grab a coffee. Browse a few shelves. Find something you didn’t know you needed. You came for coffee. You left with a book, a record, and no idea what time it is.

NINE PLUS NINE EQUALS AWESOME

Nine beach pavilions line Seaside’s Gulf front, designed by nine different architects. They’re not just ways to get from town to sand. They’re part of what makes the shoreline instantly recognizable. Even the walk to the beach has style.

PARK IT. FOR REAL.

Seaside sits between WaterColor and Seagrove, but you may not need to leave. Walk from breakfast to the beach. Wander into a shop. Grab something cold. Head back toward the Gulf. Give your car a vacation.

FRONT PORCH. FRONT-ROW SEAT.

Front porches face the streets, cottages sit close together, and brick-paved streets connect it all. The result is a neighborhood designed for people to see and be seen. Now have a seat. People-watching in Seaside? A legitimate vacation activity.

Airstream Row

AmericanBbqFrench

$$$$

Black Bear Bread Co.

American

$$$$

Great Southern Café

SeafoodSouthern

$$$$

Pickle’s Burger and Shake

American

$$$$

Bud & Alley’s Pizza Bar + Trattoria

Italian

$$$$

Meltdown on 30A

American

$$$$

Bud & Alley’s

AmericanSeafood

$$$$

The Shrimp Shack

Seafood

$$$$

Amavida Coffee and Tea

American

$$$$

Coffee at Amavida. Something warm from Black Bear Bread Co. Seaside restaurants make it easy to turn a quick bite into another reason to linger. Try Southern cooking at Great Southern Café, grab a grilled cheese from The Meltdown on Airstream Row, or settle in for seafood and Gulf views at Bud & Alley’s. Still hungry? There’s wood-fired pizza at Bud & Alley’s Pizza Bar + Trattoria. Dinner plans, sorted.

Seaside BEACH ACCESSES

W. Ruskin Access

Private To Specific Community

Odessa Private Access

Private To Specific Community

Coleman Beach Pavilion Access

Private To Specific Community

Seaside Pavilion Access

Private To Specific Community

E. Ruskin Access

Private To Specific Community

Natchez Private Access

Private To Specific Community

Savannah Access

Private To Specific Community

Tupelo Access

Private To Specific Community

Pensacola Private Access

Private To Specific Community

EVENTS OF Seaside

Sat, October 10

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place rain or shine in the Seaside Amphitheater, located adjacent to Airstream Row, local shops, and dining spots. Operating Saturdays from 9 AM to 1 PM, with additional Tuesday hours from June through July 30, the market brings together local growers and craftspeople offering healthy, environmentally conscious goods. Visitors can explore fresh produce, artisan cheeses, specialty breads, cooking demonstrations, and seed exchanges, alongside educational opportunities focused on sustainable food preparation and gardening. Beyond the weekly market, the community offers a variety of year-round, family-friendly events, including outdoor movies, morning yoga, children's theater, concerts, and holiday celebrations.

Sat, October 10

Fall Children’s Theater Show

Seaside

Family Fun

Dragons Love Tacos follows the story of a boy and his dog who discover the rules and unexpected outcomes of feeding dragons. This family-friendly production, performed by seven actors from the Emerald Coast Theatre Company, takes place on Saturdays from September 19 through October 17 at 5 PM at the Seaside Amphitheater. The event is free to the public, courtesy of the Arts & Entertainment fee collected by the Merchants of Seaside.

Tue, October 13

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market is held rain or shine at the Seaside Amphitheater on Saturdays from 9 AM to 1 PM year-round, as well as Tuesdays from 9 AM to 1 PM from June through July 30. Located adjacent to Airstream Row, the area offers access to numerous shops, dining spots, and seating areas. The market features local growers and craftspeople providing healthy, eco-friendly products, fresh produce, artisan cheeses, specialty items, and breads. It also offers cooking demonstrations, seed exchanges, and educational opportunities about food cultivation. Overall, Seaside acts as a family-friendly, year-round destination hosting events like morning yoga, outdoor movies, children's theater, and sunset concerts.

Tue, October 13

Paella with Chef Joyce

Seaside

Food & Drink

Orders for the paella begin at 6:00 PM CST, with service starting at 7:00 PM CST on a first-come, first-served basis. Plates are priced at $30 each, with the option to add soft shell crab for an additional $5. Chef Joyce originally learned her paella recipe in Spain and has since refined it with local panhandle flair, substituting traditional sausage with chorizo for an extra spicy kick. North Beach Social guests can order at the counter to receive a ticket and pick up their meal at the paella stand when service opens, while Farm & Fire guests can order at their table or the bar for tableside delivery.

Wed, October 14

Sounds of Seaside: Max McCann

Seaside

Live Music

Attendees can bring blankets and chairs to enjoy an afternoon of live local music at the Seaside Amphitheater. The October concert lineup includes performances by Roman Street on October 7, Max McCann on October 14, and BOUKOU GROOVE on October 28, with the schedule for October 21 to be determined.

Thu, October 15

Paella with Chef Joyce

Seaside

Food & Drink

Orders begin at 6:00 PM CST, followed by service at 7:00 PM CST on a first-come, first-served basis. Plates are priced at $30 each, with an option to add soft-shell crab for $5. Inspired by her time in Spain, Chef Joyce adapted her famous paella recipe to incorporate local panhandle flair, featuring spicy chorizo instead of standard sausage. Guests at North Beach Social can purchase paella tickets at the counter and pick up their food at the paella stand when service starts, while Farm & Fire guests can place orders at their table or the bar for tableside delivery.

Fri, October 16

Jared Herzog

Seaside

Live Music

Guests can catch Jared Herzog performing live from 4:00 PM to 7:00 PM.

Fri, October 16

Zack Miller

Seaside

Live Music

Audiences can attend a live performance by Zack Miller between 4:00 PM and 7:00 PM.

Sat, October 17

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place rain or shine at the Seaside Amphitheater on Saturdays from 9 AM to 1 PM, with additional Tuesday market hours offered from June through July 30. Situated adjacent to Airstream Row, shops, and dining, this producer-focused market features local growers and artisans offering eco-friendly produce, specialty items, artisan cheeses, and breads. Visitors can participate in cooking demonstrations, seed exchanges, and educational sessions on food preparation. Additionally, Seaside serves as a year-round, family-friendly destination offering various community events such as morning yoga, outdoor movies, children's theatre, and sunset concerts.

Sat, October 17

Fall Children’s Theater Show

Seaside

Family Fun

Dragons Love Tacos follows a boy and his dog as they discover the amusing ups and downs of feeding dragons. The family-friendly adventure features seven performers from the Emerald Coast Theatre Company and takes place on Saturdays from September 19 through October 17 at 5 PM at the Seaside Amphitheater. This complimentary event is sponsored by the Merchants of Seaside through the Arts & Entertainment fee.

Tue, October 20

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market is held rain or shine at the Seaside Amphitheater every Saturday from 9:00 AM to 1:00 PM, with additional Tuesday hours from June through July 30. Located adjacent to Airstream Row and nearby shops and restaurants, this producer-focused market showcases local growers and artisans offering healthy, eco-friendly products, specialty foods, and educational opportunities. Beyond the market, Seaside serves as a family-friendly destination offering year-round community events and activities.

Tue, October 20

Paella with Chef Joyce

Seaside

Food & Drink

Paella orders begin at 6:00 PM CST, with service starting at 7:00 PM CST on a first-come, first-served basis. Plates are available for $30 each, with an option to add soft shell crab for an additional $5. Chef Joyce refined her famous paella recipe during her time in Spain, adding a local panhandle touch by using chorizo for an extra spicy kick. Customers at North Beach Social can order at the counter to receive a ticket and retrieve their meals at the paella stand, while Farm & Fire guests can place orders at their table or the bar for tableside delivery.

Wed, October 21

Sounds of Seaside: Max McCann

Seaside

Live Music

Attendees are encouraged to bring blankets and chairs to enjoy an afternoon of live performances by local musicians at the Seaside Amphitheater. The schedule for October includes Roman Street on October 7, Max McCann on October 14, an artist to be determined on October 21, and BOUKOU GROOVE on October 28.

Thu, October 22

Paella with Chef Joyce

Seaside

Food & Drink

Orders for the paella event begin at 6:00 PM CST, with service starting at 7:00 PM CST on a first-come, first-served basis. Plates are priced at $30 each, with the option to add soft shell crab for an additional $5. Chef Joyce's famous recipe was inspired by her time in Spain and enhanced with panhandle flair, featuring chorizo for an extra spicy kick. North Beach Social guests can order at the counter to receive a ticket and collect their plate at the paella stand once service begins, while Farm & Fire guests can order at their table or the bar for tableside delivery.

Fri, October 23

Harrison Prentice

Seaside

Live Music

Harrison Prentice will be performing live from 4:00 PM to 7:00 PM.

Fri, October 23

Keylan Smith

Seaside

Live Music

Keylan Smith will perform live from 4:00 PM to 7:00 PM.

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

WHY SEASIDE IS A GREAT PLACE TO STAY FOR THE 30A SONGWRITERS FESTIVAL

Got the 30A Songwriters Festival on your January calendar? Staying in Seaside puts you right in the thick of it. For 2027, Friday’s kickoff headline set hits the SEASIDE® Amphitheater […]

Sep 14 Area Highlights

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

30A SONGWRITERS FESTIVAL 2027: DATES, ARTISTS, VENUES, TICKETS & WHERE TO STAY

January on 30A is usually the quieter side of the beach. Then Songwriters Festival weekend arrives. For four days, restaurants become listening rooms, town halls turn into stages, patios fill […]

Sep 09 Plan Your Trip

30A AFTER THE KIDS GO BACK TO SCHOOL: WHO COMES NEXT?

The backpacks are packed. The buses are rolling. And 30A? It doesn’t slow down, it just changes the invitation list. Once summer family season winds down, a different kind of […]

Sep 08 Plan Your Trip

EARLY BIRD OR NIGHT OWL? PICK A 30A RENTAL EVERYONE WILL LOVE

The right rental doesn’t force everyone onto the same schedule. It just gets out of the way. One person’s up before sunrise, coffee in hand, already spotting dolphins from the […]

Aug 12 Plan Your Trip

PLANNING A LARGE GROUP TRIP TO 30A: WHAT MATTERS BEYOND BEDROOM COUNT

A house that sleeps 16 and a house that actually works for 16 are not the same thing. One group arrives, and suddenly three families are sharing two bathrooms, the […]

Jul 29 Plan Your Trip

Oct 08 2026