Seaside Vacation Rentals
STAY IN Seaside
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.
DINING IN Seaside
Bud & Alley’s Pizza Bar + Trattoria
Located in the heart of Seaside, Bud & Alley’s Pizza Bar + Trattoria serves up wood-fired pizzas and Italian classics in a laid-back, outdoor setting. It’s a great place to relax with a slice and a glass of wine while enjoying Seaside’s vibrant atmosphere.
The Shrimp Shack
The Shrimp Shack is a cozy, no-frills seafood spot right on the beach. Known for its fresh, local shrimp, oysters, and crab legs, this casual joint serves up Gulf-to-table seafood with unbeatable views of the water.
Airstream Row
Airstream Row is a collection of food trailers operating out of vintage airstreams in Seaside. For whatever you’re in the mood for: crepes, gyros, icy treats, or a burst of cheesy goodness between two slices of bread, check out these gourmet canteens. Simply delish!
Amavida Coffee and Tea
A local favorite, known for its sustainably sourced beans and expertly crafted espresso drinks, Amavida Coffee and Tea has been connecting with Seaside customers for over a decade. It’s the go-to spot for quality coffee in a welcoming atmosphere.
Bud & Alley’s
With stunning waterfront views and a legendary reputation, Bud & Alley’s is a Seaside icon. The menu offers fresh coastal fare, and the rooftop bar is the perfect spot to enjoy cocktails and sunsets. Whether you’re looking for a casual bite or a more upscale meal, this spot has something for everyone.
Great Southern Café
Great Southern Café blends classic Southern flavors with modern twists, featuring a menu packed with fresh seafood, farm-to-table ingredients, and bold, creative dishes. The welcoming atmosphere and vibrant outdoor seating make it a popular spot in Seaside for both lunch and dinner. It’s a perfect place to enjoy Southern hospitality at its finest.
Black Bear Bread Co.
Black Bear Bread Co. is the neighborhood bakery and café everyone loves. From freshly baked bread to gourmet coffee and artisan pastries, this charming spot offers the perfect breakfast or light lunch. Don’t miss their seasonal sandwiches and pastries that locals rave about.
Meltdown on 30A
This fun food truck serves up gourmet grilled cheese sandwiches with inventive ingredients and tons of flavor. Located in Seaside, Meltdown on 30A is a favorite for a quick bite or a satisfying snack after a day at the beach. Their cheesy creations are sure to hit the spot for both kids and adults alike.
Pickle’s Burger and Shake
Pickle’s is a Seaside staple, famous for its juicy burgers, crispy fries, and hand-spun shakes. With its retro diner vibe, it’s a fun, family-friendly spot that’s perfect for a casual lunch or a post-beach treat.
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
Coleman Beach Pavilion Access
Pensacola Private Access
W. Ruskin Access
Savannah Access
Seaside Pavilion Access
Tupelo Access
Odessa Private Access
Natchez Private Access
E. Ruskin Access
EVENTS OF Seaside
Thu, October 2
Water Aerobics
Seaside
Workshops & Classes
This low-impact water aerobics class is designed to improve cardiovascular fitness, strength, and flexibility by utilizing the natural resistance of water. It offers a full-body workout that is gentle on the joints, making it suitable for individuals with arthritis, joint pain, or those seeking a softer alternative to land-based exercises. Whether improving fitness, recovering from an injury, or enjoying a refreshing workout, this class provides an excellent way to stay active and have fun in the pool at The West Side Pool. Fees apply for this class.
Learn More
Thu, October 2
Water Aerobics
Seaside
Workshops & Classes
This low-impact water aerobics class is designed to improve cardiovascular fitness, strength, and flexibility by utilizing the natural resistance of water. It offers a full-body workout that is gentle on the joints, making it suitable for individuals with arthritis, joint pain, or those seeking a softer alternative to land-based exercises. Whether improving fitness, recovering from an injury, or enjoying a refreshing workout, this class provides an excellent way to stay active and have fun in the pool at The West Side Pool. Fees apply for this class.
Learn More
Thu, October 2
Camp SEASIDE®: Scavenger Hunt
Seaside
Family Fun
The Camp Seaside Scavenger Hunt is an exciting journey through a vibrant beach town, filled with fun clues, local landmarks, and hidden surprises. Kids will team up, follow a custom clue sheet, and race to find special spots and treasures, all while learning about Seaside’s coolest corners. Participants can expect a fun, kid-friendly clue sheet and prizes for completed cards and extra spirit. They should bring comfy shoes, a water bottle, and keen observation skills. This event is described as part treasure hunt, part town tour, and 100% Camp Seaside fun.
Learn More
Thu, October 2
Paella Night!
Seaside
Food & Drink
Orders begin at 5:30 PM CST, with service starting at 7 PM CST, and are available on a first-come, first-served basis. Chef Joyce developed her renowned paella recipe in Spain, and she has since adapted it over the years to incorporate local influences. Her unique addition of chorizo, instead of traditional sausage, provides an extra spicy kick, making this dish particularly flavorful. At North Beach Social, customers can order paella at the counter and receive a ticket, which they can then exchange for their plates at the paella stand when service commences. Farm & Fire customers have the convenience of ordering at their table or at the bar, with the dish being delivered directly to them.
Learn More
Fri, October 3
Central Square Cinema: Scoob!
Seaside
Family Fun
Attendees are invited to bring blankets and chairs for a family movie night at the Seaside Amphitheater. The movie starts at 8:00 PM, weather permitting. A schedule for October movies is provided: Scoob! on October 3, Air Bud on October 10, E.T. on October 17, Halloweentown on October 24, and Wizard of Oz on October 31. Families can review movie suitability.
Learn More
Sat, October 4
Farmers Market
Seaside
Markets & Shopping
The Seaside Farmers Market welcomes visitors from 9:00 AM to 1:00 PM. This market features local growers and artisans who offer food throughout the year.
Learn More
Mon, October 6
Camp SEASIDE®: Tennis and Pickleball Games
Seaside
Sports & Games
The Red Bar is a popular restaurant and bar in Grayton Beach, known as a local institution. It offers a fun atmosphere with eclectic decor, live music, and good food and cocktails. The Red Bar Jazz Band performs on stage during dinner Tuesday through Saturday from 5:30 PM to 9:00 PM. A variety of local and visiting bands also play on Sundays for brunch, Sunday nights, and Monday nights. The Red Bar is open daily, serving lunch and dinner with both indoor and outdoor seating options.
Learn More
Tue, October 7
Paella Night!
Seaside
Food & Drink
Stock & Trade Design Co. is hosting Gala & Golf: A Gatsby Affair, a two-day charitable event on October 4–5, 2025. This event, taking place in Santa Rosa Beach and Miramar, FL, will benefit Harlan's Place Foundation. The weekend will conclude on Sunday with a charity golf tournament. All proceeds from the event will support Harlan's Place Foundation, a nonprofit dedicated to creating compassionate housing and community programs for adults with Down syndrome and intellectual disabilities, and empowering individuals with Down syndrome and intellectual disabilities to live full, vibrant lives. The event is open to individuals and foursomes, promising a memorable day of golf, good company, and meaningful impact. Volunteers, sponsors, and silent auction items are still needed to make this unforgettable weekend possible and support this meaningful cause.
Learn More
Wed, October 8
Sounds of Seaside: Fred Domulot
Seaside
Live Music
Learn More
Thu, October 9
Water Aerobics
Seaside
Workshops & Classes
Learn More
Thu, October 9
Camp SEASIDE®: Scavenger Hunt
Seaside
Family Fun
Learn More
Thu, October 9
Paella Night!
Seaside
Food & Drink
Learn More
Fri, October 10
Central Square Cinema: Air Bud
Seaside
Family Fun
Attendees are invited to bring blankets and chairs for a family movie night at the Seaside Amphitheater. The movie starts at 8:00 PM, weather permitting. The October movie schedule includes Scoob! on October 3, Air Bud on October 10, E.T. on October 17, Halloweentown on October 24, and Wizard of Oz on October 31.
Learn More
Thu, October 2
Water Aerobics
Seaside
Workshops & Classes
This low-impact water aerobics class is designed to improve cardiovascular fitness, strength, and flexibility by utilizing the natural resistance of water. It offers a full-body workout that is gentle on the joints, making it suitable for individuals with arthritis, joint pain, or those seeking a softer alternative to land-based exercises. Whether improving fitness, recovering from an injury, or enjoying a refreshing workout, this class provides an excellent way to stay active and have fun in the pool at The West Side Pool. Fees apply for this class.
Thu, October 2
Water Aerobics
Seaside
Workshops & Classes
This low-impact water aerobics class is designed to improve cardiovascular fitness, strength, and flexibility by utilizing the natural resistance of water. It offers a full-body workout that is gentle on the joints, making it suitable for individuals with arthritis, joint pain, or those seeking a softer alternative to land-based exercises. Whether improving fitness, recovering from an injury, or enjoying a refreshing workout, this class provides an excellent way to stay active and have fun in the pool at The West Side Pool. Fees apply for this class.
Thu, October 2
Camp SEASIDE®: Scavenger Hunt
Seaside
Family Fun
The Camp Seaside Scavenger Hunt is an exciting journey through a vibrant beach town, filled with fun clues, local landmarks, and hidden surprises. Kids will team up, follow a custom clue sheet, and race to find special spots and treasures, all while learning about Seaside’s coolest corners. Participants can expect a fun, kid-friendly clue sheet and prizes for completed cards and extra spirit. They should bring comfy shoes, a water bottle, and keen observation skills. This event is described as part treasure hunt, part town tour, and 100% Camp Seaside fun.
Thu, October 2
Paella Night!
Seaside
Food & Drink
Orders begin at 5:30 PM CST, with service starting at 7 PM CST, and are available on a first-come, first-served basis. Chef Joyce developed her renowned paella recipe in Spain, and she has since adapted it over the years to incorporate local influences. Her unique addition of chorizo, instead of traditional sausage, provides an extra spicy kick, making this dish particularly flavorful. At North Beach Social, customers can order paella at the counter and receive a ticket, which they can then exchange for their plates at the paella stand when service commences. Farm & Fire customers have the convenience of ordering at their table or at the bar, with the dish being delivered directly to them.
Fri, October 3
Central Square Cinema: Scoob!
Seaside
Family Fun
Attendees are invited to bring blankets and chairs for a family movie night at the Seaside Amphitheater. The movie starts at 8:00 PM, weather permitting. A schedule for October movies is provided: Scoob! on October 3, Air Bud on October 10, E.T. on October 17, Halloweentown on October 24, and Wizard of Oz on October 31. Families can review movie suitability.
Sat, October 4
Farmers Market
Seaside
Markets & Shopping
The Seaside Farmers Market welcomes visitors from 9:00 AM to 1:00 PM. This market features local growers and artisans who offer food throughout the year.
Mon, October 6
Camp SEASIDE®: Tennis and Pickleball Games
Seaside
Sports & Games
The Red Bar is a popular restaurant and bar in Grayton Beach, known as a local institution. It offers a fun atmosphere with eclectic decor, live music, and good food and cocktails. The Red Bar Jazz Band performs on stage during dinner Tuesday through Saturday from 5:30 PM to 9:00 PM. A variety of local and visiting bands also play on Sundays for brunch, Sunday nights, and Monday nights. The Red Bar is open daily, serving lunch and dinner with both indoor and outdoor seating options.
Tue, October 7
Paella Night!
Seaside
Food & Drink
Stock & Trade Design Co. is hosting Gala & Golf: A Gatsby Affair, a two-day charitable event on October 4–5, 2025. This event, taking place in Santa Rosa Beach and Miramar, FL, will benefit Harlan’s Place Foundation. The weekend will conclude on Sunday with a charity golf tournament. All proceeds from the event will support Harlan’s Place Foundation, a nonprofit dedicated to creating compassionate housing and community programs for adults with Down syndrome and intellectual disabilities, and empowering individuals with Down syndrome and intellectual disabilities to live full, vibrant lives. The event is open to individuals and foursomes, promising a memorable day of golf, good company, and meaningful impact. Volunteers, sponsors, and silent auction items are still needed to make this unforgettable weekend possible and support this meaningful cause.
Wed, October 8
Sounds of Seaside: Fred Domulot
Seaside
Live Music
Thu, October 9
Water Aerobics
Seaside
Workshops & Classes
Thu, October 9
Camp SEASIDE®: Scavenger Hunt
Seaside
Family Fun
Thu, October 9
Paella Night!
Seaside
Food & Drink
Fri, October 10
Central Square Cinema: Air Bud
Seaside
Family Fun
Attendees are invited to bring blankets and chairs for a family movie night at the Seaside Amphitheater. The movie starts at 8:00 PM, weather permitting. The October movie schedule includes Scoob! on October 3, Air Bud on October 10, E.T. on October 17, Halloweentown on October 24, and Wizard of Oz on October 31.
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
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 2025 ON 30A: HOW TO CELEBRATE TURKEY DAY BEACH STYLE
Thanksgiving on 30A is all about coastal charm, good food, and fun with friends and family… with a side of sand between your toes. From morning races to festive feasts, […]
Sep 10 Plan Your Trip
A LAID-BACK LABOR DAY ON 30A
Labor Day weekend along 30A has its own rhythm. The Gulf is still warm, the pace slows down, and suddenly the last long weekend of summer feels like a neighborhood […]
Aug 19 Plan Your Trip
BEACH SAFETY TIPS FOR 30A SUMMERS
A light, helpful guide to smarter days on the sand. Summer on 30A is the stuff of vacation dreams. But before you sprint into the Gulf like it’s a backyard […]
Jun 27 Plan Your Trip
FOURTH OF JULY EVENTS ON 30A, FLORIDA
The Fourth of July on 30A isn’t just a holiday. It’s an art form. Golf carts become parade floats. The beach becomes your front-row seat to a light show. And […]
May 12 Plan Your Trip
THERE'S MORE TO EXPLORE ON 30A
Along County Road 30A are communities that shimmer. The several small beach towns are simply delightful, running between Panama City and Destin.
