221 Seaside Holiday Rentals

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Compare Seaside holiday rentals from 6 rental sites including HomeAway, TripAdvisor, Booking.com and more, from $65 a night.

Information about Seaside

About Seaside

Seaside is located between Panama City Beach and Destin on the Florida Panhandle. Established in 1981, it manages to exude small town charm from a much older, more simple, pre-WWII era. Offering quant and lively downtown dining and shopping, Seaside was recently named Travel + Leisure’s “Best Beach on Earth”. It was also included in the “Top 10 Best Beach Towns in Florida” by USA Today (2013).

Its architecture, with Charleston, Antebellum, and Victorian influences, has also gained prominence. It’s included in the American Institute of Architects list of Florida Architecture: 100 Years 100 Places.

Things To Do in Seaside

Beside the pastel-colored small town lies the Gulf of Florida’s white sand beaches and turquoise waters. If you’d like to reserve a beach chair and awning during your stay, book through Cabana Man. They also rent ocean kayaks and paddle boards.

At Seaside Beach you can even take surf lessons through Austin Magee’s Surf School. Stop by Beach Ready Spa and get a deep-tissue massage or a facial for a more relaxing experience. During summertime, Seaside Farmer’s Market sets up on Saturdays between 9am and 1pm. Local growers, bakers, and local artisans sell fresh and unique wares to peruse.

Become acquainted with the downtown area and explore the specialty gift shops, art galleries, book stores, and clothing boutiques. Highlights include Sundog Books with a great selection, Central Square Records for music, Newbill Collection by the Sea for keepsakes, and Fusion Art Gallery.

Food trucks line the main road (County Road 30-A) in the middle of town. There you will find BBQ, hot dogs, shaved ice, grilled cheese, grills, and coffee. Can’t-miss local restaurant cuisine also includes southern cooking and fresh seafood at Great Southern Café.

For nightly entertainment, stop by the Seaside Repertory Theatre and see a comedy or drama from the area’s only professional theatre troupe. You can also check out the Seaside events calendar for festivals, outdoor concerts, markets, theatre productions, and a schedule of movie showings under the stars!

Day Trips From Seaside

Panama City Beach is a hot spot for vacationers for its wide range of recreation. You can hop on a shuttle from St. Andrews State Park to Shell Island, an untouched island between the bay and the Gulf of Mexico. Or you can walk Pier Park for Miracle Strip Amusement Park and other activities, including bungee jumping! By night, Panama City Beach runs the gamut between dive bars and bottle-service clubs. But you can’t go wrong with local seafood shacks for oysters and atmosphere. Try Gene’s Oyster Bar for a quintessential southern seafood fix (cash only).

A 40-minute drive in the opposite direction along the Emerald Coast brings you to Destin, a beach and golf course destination offering shopping, plenty of watersports, and fishing charters. Horseback ride in Destin through nearly 14,000 acres of State Forest, or take a nature hike with Mattie Kelly Park and Nature Walk. The Boardwalk, Wharf, and HarborWalk Village are some of the top destinations for lively atmosphere and nightlife.

Seaside Accommodations

The city was planned so that buildings were limited to a maximum height of just 3 stories so as not to block the ocean view for homeowners. The homes themselves feature wide porches, large windows, and the world renowned architecture that agrees with easy beach living.

Enjoy Seaside resort town from the heart of it. You can find over 250 rental options on Tripping.com. Choose from a selection of oceanside cottages on the beach and plantation-style homes with gazebos and backyard pools.

Transportation In Seaside

Everything is within Seaside is within walking distance, but you can also rent a bike or golf cart to get around locally.

The nearest airport is Northwest Florida Beaches International (ECP/KECP), located about 30 miles from Seaside. You can also arrive through Northwest Florida Regional Airport (VPS/KVPS), only 39 miles from downtown. You can use Sunshine Shuttles to book transportation from an airport to town.

Vacation Rentals in Seaside

Find the best Seaside vacation rentals with Tripping.com. Choose from 221 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices from $65 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 186 of homes in Seaside offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 163 rentals with pool or jacuzzi, or relax with the family in one of the 139 homes with cable TV.

For all those dog lovers and cat lovers, Seaside offers 6 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 6 rental sites in Seaside where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 117 HomeAway rentals, 44 TripAdvisor short term rentals and 36 Booking.com vacation rentals.