As the holiday season arrives, the hunt for unique and meaningful gifts becomes a cherished tradition. Instead of braving the bustling malls and department stores, why not embrace the enchanting atmosphere of small-town charm for your Christmas shopping? Orlando and Central Florida has a wide collection of adorable small towns that transform into winter wonderlands during the holidays. Below are some small-town shopping districts where you can discover one-of-a-kind treasures that your family and friends will cherish. 

And while you're out and about, make time to enjoy some of the best Christmas light displays nearby. Or enjoy one of the many free holiday season events.

Orlando’s Small Towns for Christmas Shopping

We have featured some local favorite shops, but they are only the beginning of your shopping experience with these lovely hometowns. We'll start off with the small towns closest to Orlando that are best for the holiday season. Then we're sharing a few that are worth a bit of a drive. 

Keep in mind that small towns run on their own schedules and many stores may not be open on Sundays. Make sure to do a little research ahead of time if you are thinking about going on a Sunday.

Festive small towns closest to Orlando

  • Winter Garden
  • Historic Downtown Longwood
  • Downtown Sanford
  • Celebration
  • Winter Park
  • Downtown DeLand

Winter Garden

Shopping District: Plant Street

Just west of Orlando is the picturesque town of Winter Garden, a holiday hub for locally crafted gifts. With the delightful backdrop of the West Orange Trail and the city's historic charm, Winter Garden's Christmas shopping experience is nothing short of magical, making it an ideal destination for those in search of distinctive gifts and holiday cheer.

Merry Winter Garden Light Show

Local favorite shops: 

  • Adjectives Market – Furniture, decor, and gift store that offers an extensive range of diverse styles
  • Writer’s Block Bookstore – a sanctuary for book worms that offers all types of books, from Indie to The New York Times Best Sellers.
  • AntiquiTEAs – a purveyor of fine loose-leaf tea blends, local honey and infusers for home brewing.
  • Polka Dotz – jewelry store featuring favorite brands such as PANDORA, Kendra Scot, Swarovksi and more!

Historic Downtown Longwood

Shopping District: Church Ave

Many Orlando and Seminole County residents drive through historic downtown Longwood without a second thought about the shops and small businesses here. But during the holiday season, this charming little downtown area gets into the holiday spirit and is a hidden gem.

Park in any of the ample parking lots off Jessup Avenue, Church Ave, Community Park, or Reiter Park. Plus every Saturday there is the Longwood Farmers' Market, one of the best Orlando farmers' markets for kids.

Fuel your shopping adventure with a stop at Claro's Coffee or Alestone Brewing.

White pizza and craft beer at Alestone Brewing Company in Longwood
White pizza and craft beer at Alestone Brewing Company in Longwood | Dani Meyering

Local favorite shops:

  • Judy's Doll Shop – an absolutely must visit for anyone who wants to relive childhood memories
  • Ruby Sun Gifts – explore unique gifts, seasonal decor, and Florida finds inside a circa 1881 cottage
  • Cottage Gift Shop – Florida themed gifts found inside a cottage built in circa 1870 and moved from Boston in 1873, is one of the oldest prefabricated houses in the United States.
Cottage Gift Shop Christmas Shopping Downtown Longwood Near Orlando -
Cottage Gift Shop Downtown Longwood – image by Dani Meyering

Downtown Sanford

Shopping District: East First Street

Located on the banks of Lake Monroe, Sanford offers a unique Christmas shopping experience. These charming brick-lined streets are filled with art galleries, music shops, and cultural storefronts.

exterior of magnolia square market with german flag hanging in front of the entrance and outdoor seating
Magnolia Square Market in Sanford – Dani Meyering

The city hosts free holiday events and markets, such as the Sanford Christmas Parade and the Alive After 5 Holiday Street Party, providing a vibrant and joyful ambiance for shoppers. Whether you're searching for artisanal gifts, antiques, or trendy holiday fashion, Sanford's cozy and welcoming shopping scene makes the holiday season all the more magical.

Local favorite shops: 

  • Hollerbach’s Outfitters – a local source of traditional German folkwear and artifacts.
  • Gallery on First – unique gallery featuring professional and emerging artists where they display their art for purchase.
  • Magpies Modern General Store – A curated collection of heartfelt and hilarious have-to-have gifts. 
  • Wondermade – Homemade marshmallows in a large and unique variety of flavors such as lavender, S’mores, Key Lime Pie, and even… beer!


Shopping District: Celebration Ave

A once dreamt utopian paradise planned by the Walt Disney Company, Celebration is a festive community that exudes storybook charm. During the holiday season, the town is transformed into a winter wonderland, complete with ice rink, horse carriage rides, and a towering Christmas tree.

Shopping here will surely get you into the Christmas spirit, with boutiques and eclectic shops.

Local favorite shops:

  • Market Street Gallery – unique gifts for theme park and christmas decor enthusiasts.
  • Vintage Vibes – featuring trendy clothes, accessories, and curiosities. 
  • Soft as Grape – a family-owned shop featuring comfortable resort wear. 

Winter Park

Shopping District: Park Avenue

Winter Park’s Park Avenue is a shopper’s paradise year-round, but during the holidays, it comes to life. Lined with boutique stores, upscale shops, and quaint cafes, you will be sure to find a large range of gifts for everyone on your list this season. 

Looking at Briar Patch Restaurant on Park Avenue Winter Park Florida
Park Avenue Winter Park – image by Dani Meyering

Local favorite shops: 

  • HAVEN Uncommon Good – from clothing and hand-sewn pillows to vintage decor and artisan crafted items, this store is highlighted by its professionally curated selection. 
  • Loving Thyself Rocks – a metaphysical supplies store that has an array of crystals, geodes, incense.
  • The Partridge Tree Gift Shop – considered a one stop shop for all your gift needs, specializing in unique and quality gifts.
  • Ten Thousand Villages – a fair trade retailer with artisan-crafted home decor, accessories and gift items from across the globe. 

Downtown DeLand 

Shopping District: Woodland Boulevard

DeLand is another historic district that offers a Victorian-style Christmas experience like no other. The downtown area truly comes to life with twinkling lights, cheerful decorations, and a sense of community spirit.

From antique and vintage shops to boutiques and homemade treats, Downtown DeLand will surely be the spot that will help you get some wish list gifts marked off. The city hosts various holiday events and markets, so be sure to check out their website for dates and times. 

Cocktails from The Table in downtown DeLand
Cocktails from The Table in downtown DeLand – image by Dani Meyering

Local favorite shops: 

  • Pat and Toni’s Sweet Things – features old fashioned candy with homemade chocolates and fudge
  • Orchid Rain – an eclectic shop with boho inspired gifts
  • Marketplace at Rivertown – a market-style antique and vintage shop
  • Shellsea – boutique clothing store featuring trending styles

*Bonus: Attend DeLand’s weekly Artisan Alley Farmers Market to score some handmade gifts and treats. Every Friday from 6:00pm to 9:00pm 

Shopping in Small Towns Worth the Drive from Orlando

Mount Dora

Shopping District: Donnelly Street

The historic town of Mount Dora becomes a true Hallmark movie during the holiday season. The streets are adorned with thousands of lights, and the local shops and boutiques offer an array of handcrafted gifts, vintage finds, and unique trinkets. Mount Dora captures the spirit of the season and makes Christmas shopping a memorable and heartwarming experience.

Local Favorite shops to consider: 

  • Wow Factory – features fun novelties and edgy gifts
  • Under the Cherry Blossoms – features handmade gifts from over 20 local artists
  • Mount Dora Olive Company – features delectable and gourmet gifts such as various flavored oils and vinegars
  • Piglets Pantry – for your four legged family members

New Smyrna Beach

Shopping District: Flagler Avenue and Canal Street

Christmas shopping in New Smyrna is a delightful experience that combines the charm of a coastal town with the festive spirit of the holiday season. Stroll along Flagler Ave, where the palm trees are adorned with twinkling lights, and a variety of locally-owned boutiques and shops offer unique gifts and souvenirs.

Canal Street Storefronts New Smyrna Beach - Dani Meyering
Canal Street Storefronts New Smyrna Beach – Dani Meyering

You can explore a trove of beach themed ornaments, artisanal crafts, and fashionable beachwear that make for perfect presents. The warm and welcoming atmosphere, coupled with the coastal breeze, creates a relaxing shopping experience you won't soon forget. 

Local favorite shops: 

  • Friki Tiki – an ever changing assortment of tropical finds
  • Gypsy Vibes – an eclectic array of boho and global inspired items such as Fair Trade home decor, handmade jewelry, healing gems and more.
  • Silly Willie’s Dog & Cat Stuff – unique gifts and boutique for your furry friends

St. Augustine Shopping

Shopping District: St. George Street

Christmas shopping in St. Augustine, Florida, is a truly enchanting experience that combines the city's rich history with the magic of the holiday season, especially with Nights of Lights.

Old Town Trolley and Flagler College during St Augustine Nights of Lights
St Augustine Nights of Lights Tour – Image by Old Town Trolley Tours

Whether you're looking for historical keepsakes, locally-made treasures, or simply soaking in the holiday spirit, St. Augustine provides a magical backdrop for your Christmas shopping adventure.

Local Favorite Shops: 

  • Mustache: Merchant of Man – all kinds of unique gifts for your dude
  • Aunt Matilda’s Steampunk Trunk – a clothing store with a fun steampunk theme
  • Prehistoric Florida – an interesting store with a variety of meteorites, fossils and minerals
  • Tervis Store – a large selection designs and add-on of the popular durable drinkware

Also consider: