Located about 72 miles east of Pensacola is Seaside, Florida – the first planned New Urbanist-style community. Spanning 80 acres of beachfront, Seaside embraces small-town traditions, with walkable streets and a shopping village in the center. Its famous pastel-colored houses make lovely vacation rental homes. Featuring porches and white picket fences, the cozy vacation cottages, tucked behind rows of live oak trees, will make you feel like you’ve entered a different era. When they aren’t lounging at the community pool or relaxing on a park bench, visitors can bike to the beach and nearby Grayton State Park. You don’t need a beachfront rental to enjoy a vacation at Seaside – there’s so much to see and do in this lovely oceanside town.

Seaside Vacation Rentals

You won’t find any resort hotels in Seaside – all the vacation rentals are houses or condos. Vacation homes range in size from studio guest houses to small cottage rentals, to large family homes.

Guest Houses

Guest houses are located on the same property as a larger home and make a charming getaway for two. Cottage-style details like wood plank walls, shutters, and painted furnishings create a casual, beachy vibe. Rent a guest house by itself, or as an add-on to the main house if you have a large group.


While all the Seaside homes for rent are known as Cottages, the smaller homes indeed have that cottage feeling. One- or two-bedroom cottages have front porches and traditional carpentry details that evoke turn-of-the-last-century American towns. Each home has a unique picket fence design, and sandy pathways between the houses make it seem as if the village grew over time.

If you have a large family or are planning a wedding or reunion, consider one of the larger homes for rent. Cottages at Seaside are available with up to six bedrooms, and you can add a studio guesthouse to accommodate even more people. These vacation properties offer such amenities as large decks, third-floor towers to take in the views, bunk rooms, and free cruiser bikes.

Having everyone together is one of the best features of Seaside’s vacation rentals. Throw a destination wedding or get all the generations together for a celebration. Leave the car parked too – you can walk or bike all over town.

Things to Do in Seaside, Florida

The white sand beaches of Seaside may be the primary draw for tourists, but there are plenty of other ways to enjoy nature. Nearby, you can walk the nature trails or rent a kayak at Grayton Beach State Park. Tour a historic mansion and garden at Eden Gardens State Park, just a short 10-minute drive away.

Shopping is always fun when you’re traveling, and Seaside doesn’t disappoint. This town has an impressive selection of unique shops – grab some culture at Sundog Books or Central Square Records. Shop for gourmet goods at Modica Market. Ann Hunter Gallery and The Newbill Collection’s selection of art, crafts, and gifts are the perfect spots to souvenir-shop. If it’s raining, head over to Fired-Up Pottery Painting to create your own masterpiece. Plus, you can walk or bike over from your cottage rental! Seaside, Florida is one of those towns where you can spend hours exploring the shops and galleries.

Seaside’s Best Restaurants

One of the best foodie treats at Seaside might be the Airstream trailer food stands that line the square – walk on up to sample street foods like raw juices, melted cheese sandwiches, creative barbeque recipes, and gourmet hot dogs.

Pickle’s Beachside Grill is an open-air diner featuring organic, free-range beef burgers. Amavida Coffee offers fair trade coffee, pastries, and sandwiches, and is open for dinner too. Order breakfast, brunch, lunch, and dinner at the local favorite, Great Southern Café. Locally sourced meat and seafood is the specialty here. Don’t miss the Grits a Ya Ya: blackened shrimp and smoked bacon on smoked Gouda cheese grits topped with sweet potato hay. Yum!

Schedule an evening out at Crush – its outdoor patio is beside the amphitheater, so you can catch Seaside’s summer jazz concerts. The lunch and dinner menus offer sushi, fresh fish tacos, and a daily cheese board. Choose from 24 wines by the glass.

If you want your seafood right off the beach, take in the sunset at The Shrimp Shack right on the sand.  Or take in a more expansive view from Bud & Alley’s rooftop bar.  Whether you’re looking for fine dining or fresh peel-n-eat shrimp overlooking the waves, you’ll find your cravings satisfied without ever leaving Seaside.

Annual Events in Seaside, FL

One of the primary visions the founders of Seaside had was creating a sense of belonging. Keeping the calendar full of events is one of the ways Seaside creates its inherent sense of community. Visitors can walk or bike to everything from their vacation rental.

The Saturday Farmer’s Market brings everyone together for local produce and gourmet foods. The grassy amphitheater is home to jazz concerts and theatrical performances throughout the year.

Seaside’s artist-in-residence program, Escape to Create, brings a group of accomplished artists to the town each year to perform and teach theater, music, painting, and sculpture. Holiday events include a November Wine Festival, the Turn on the Town lighting ceremony, a performance of the Nutcracker, and a holiday film in the outdoor cinema.

No matter what time of year you visit Seaside, you’ll find plenty to do!