Seaside Vacation Rentals

STAY IN Seaside

Ingle's Nest

Sleeps 8 - 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

$$$$

Great Southern Café

SeafoodSouthern

$$$$

Black Bear Bread Co.

American

$$$$

Meltdown on 30A

American

$$$$

The Shrimp Shack

Seafood

$$$$

Pickle’s Burger and Shake

American

$$$$

Amavida Coffee and Tea

American

$$$$

Bud & Alley’s

AmericanSeafood

$$$$

Bud & Alley’s Pizza Bar + Trattoria

Italian

$$$$

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

Tupelo Access

Private To Specific Community

Natchez Private Access

Private To Specific Community

Savannah Access

Private To Specific Community

Odessa Private Access

Private To Specific Community

W. Ruskin Access

Private To Specific Community

Pensacola Private Access

Private To Specific Community

Coleman Beach Pavilion Access

Private To Specific Community

E. Ruskin Access

Private To Specific Community

Seaside Pavilion Access

Private To Specific Community

EVENTS OF Seaside

Tue, November 10

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place rain or shine at the Seaside Amphitheater on Saturdays from 9:00 AM to 1:00 PM year-round, as well as Tuesdays from 9:00 AM to 1:00 PM from June through July 30. Located next to Airstream Row, the producer-focused market features local growers and craftspeople offering healthy, environmentally conscious foods, produce, artisan cheeses, specialty items, cooking demonstrations, and educational opportunities.

Tue, November 10

Paella with Chef Joyce

Seaside

Food & Drink

Chef Joyce prepares her signature Spanish-style paella with a regional twist on a first-come, first-served basis, with orders opening at 6:00 PM CST and service beginning at 7:00 PM CST. Plates cost $30, with an option to add soft-shell crab for $5. Guests at North Beach Social can order at the counter for pickup, while Farm & Fire guests receive table or bar service.

Wed, November 11

Flow Tribe

Seaside

Live Music

Attendees are invited to bring blankets and chairs to enjoy live music performances by local artists at the Seaside Amphitheater throughout November. The lineup includes Max McCann on November 4, Flow Tribe on November 11, Roman Street on November 18, and BOUKOU GROOVE on November 25.

Thu, November 12

Paella with Chef Joyce

Seaside

Food & Drink

Chef Joyce serves her signature paella recipe inspired by her time in Spain, featuring chorizo for a spicy kick. Orders 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 an optional soft-shell crab add-on for $5. North Beach Social guests can order at the counter for a pickup ticket, while Farm & Fire guests can order at their table or the bar for tableside delivery.

Fri, November 13

Jared Herzog

Seaside

Live Music

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

Fri, November 13

Keylan Smith

Seaside

Live Music

Musician Keylan Smith performs a live musical set from 4:00 PM to 7:00 PM.

Sat, November 14

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place rain or shine in the Seaside Amphitheater on Saturdays from 9:00 AM to 1:00 PM and Tuesdays from 9:00 AM to 1:00 PM through July 30. Local growers and craftspeople offer healthy, environmentally conscious foods, produce, artisan cheeses, specialty items, and educational opportunities.

Tue, November 17

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place in the Seaside Amphitheater on Saturdays from 9:00 AM to 1:00 PM, as well as Tuesdays from June through July 30. Local growers and artisans offer fresh produce, specialty foods, cheeses, and crafts alongside educational activities and cooking demonstrations.

Tue, November 17

Paella with Chef Joyce

Seaside

Food & Drink

Chef Joyce serves her famous Spanish paella infused with local panhandle flair and chorizo for an extra kick. Ordering begins at 6:00 PM CST with service at 7:00 PM CST on a first-come, first-served basis at $30 per plate, with soft shell crab available for an additional $5. North Beach Social guests can order at the counter and collect their plates from the paella stand, while Farm & Fire guests can order from their table or the bar for tableside delivery.

Wed, November 18

Roman Street

Seaside

Live Music

Guests can bring blankets and lawn chairs for afternoon live music performances at the Seaside Amphitheater in November. The local musician schedule features Max McCann on November 4, Flow Tribe on November 11, Roman Street on November 18, and BOUKOU GROOVE on November 25.

Thu, November 19

Paella with Chef Joyce

Seaside

Food & Drink

Guests can enjoy Chef Joyce's Spanish paella with panhandle flair, featuring chorizo for an added spicy kick. Orders open at 6:00 PM CST and service begins at 7:00 PM CST on a first-come, first-served basis for $30 per plate, with an option to add soft shell crab for $5. North Beach Social guests can order at the counter to receive a ticket and pick up their plate at the paella stand, while Farm & Fire guests can order at their table or bar for tableside delivery.

Fri, November 20

Emily Bass

Seaside

Live Music

Guests can catch a live performance by Emily Bass from 4:00 PM to 7:00 PM.

Fri, November 20

Keylan Smith

Seaside

Live Music

Attendees can catch Keylan Smith performing live from 4:00 PM to 7:00 PM.

Sat, November 21

Farmers Market

Seaside

Markets & Shopping

The Seaside Farmers Market takes place rain or shine in the Seaside Amphitheater every Saturday from 9:00 AM to 1:00 PM, as well as Tuesdays from June through July 30th. Featuring local growers and artisans, the market offers fresh produce, specialty foods, artisan cheeses, breads, and healthy products alongside cooking demonstrations and educational activities.

Sun, November 22

The Nutcracker Ballet Act II

Seaside

Arts & Culture

Ballet Pensacola presents a free public performance of Tchaikovsky's The Nutcracker Act II at the Seaside Amphitheater Stage on Sunday, November 22, 2026, at 5:00 PM. Attendees are encouraged to bring lawn chairs and blankets.

Tue, November 24

Paella with Chef Joyce

Seaside

Food & Drink

Chef Joyce offers Spanish paella with a panhandle twist at North Beach Social and Farm & Fire. Ordering opens at 6:00 PM CST and service begins at 7:00 PM CST on a first-come, first-served basis for $30 per plate, with optional soft shell crab for $5.

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

THANKSGIVING ON 30A IN 2026: WHERE TO EAT, WHAT TO DO & WHERE TO STAY

Thanksgiving at the beach comes with a few welcome additions: a walk along the Gulf, a porch for your morning coffee, and holiday lights waiting just down the road. In […]

Oct 29 Plan Your Trip

NEW YEAR’S EVE ON 30A: FIND YOUR BEACH HOME FOR 2027

Plan your stay: December 30, 2026–January 3, 2027 The best part of a New Year’s beach trip might happen after the countdown: coffee with a Gulf view, a breakfast that […]

Oct 27 Plan Your Trip

STILL TIME FOR HALLOWEEN ON 30A: 5 BEACH STAYS WE’D PICK

There’s still time to make Halloween a beach weekend. Oversee has homes showing availability for Friday, October 30, through Sunday, November 1, including a stay in Seaside itself. And with […]

Oct 21 Plan Your Trip

HALLOWEEN ON 30A IN 2026: TRICK-OR-TREATING, PUMPKIN PATCHES & A BEACH WEEKEND AWAY

Pack the costumes next to the beach towels. Halloween on 30A gives you a good reason to squeeze in one more family trip before the holiday season takes over. There […]

Oct 21 Plan Your Trip

Oct 08 2026