0 Bedrooms for 1 Guest
Price $10 - $1000+

5,211 Seaside Vacation Rentals & Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Seaside vacation rentals from 10 rental sites including HomeAway, TripAdvisor, PerfectPlaces, and more, ranging from $25 to $9000 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

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Seaside offers 5,202 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $320 a night, or a long-term rental for an average price of $5875 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 4,402 of Seaside’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 3,473 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 4,284 cozy homes.

    Traveling with pets? Choose from 435 pet-friendly rentals in Seaside for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

    Search properties from 10 rental sites in Seaside where the top providers in that area are HomeAway, TripAdvisor, and PerfectPlaces. There are 3,416 HomeAway rentals, 682 TripAdvisor short term rentals and 438 PerfectPlaces vacation rentals.