Kissimmee, Florida

Shop the City

Uncover the best retail in Kissimmee, Florida

By Jenn Thai, This Jenn Girl

To me, Kissimmee is a hidden gem when it comes to shopping—while most are only familiar with the city as a destination for Disney-goers, those who take the time to explore further will realize it yields a treasure trove of shopping opportunities for both staycationers and out-of-towners alike. From a high-end retail experience at The Mall at Millenia to an excursion at Disney Springs that will elevate both your culinary and fashion senses, there’s so much to do and discover in Kissimmee!

During a three-day weekend stay, I got the opportunity to delve into all that the city has to offer shopping-wise, and I’m so excited to share my 72-hour shop-the-city adventure with you!

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Saturday, 11 a.m.—The Mall at Millenia

The Mall at Millenia exudes an ambiance like no other, with ambient instrumentals that reverberate through Grand Court and its circular terrazzo, and stunning natural light that shines through conservatory-like skylights. Even if you don’t physically go inside a store, the atmosphere of this popular destination fully encourages window shopping. The Mall at Millenia is a world-class hub for shopping, featuring favorite stores like H&M, LOFT, Banana Republic and Urban Outfitters, as well as top luxury brands like Gucci, Louis Vuitton and Chanel.

The first store I made my way to was H&M, and compared to other ones that I’ve been to, this one had by far an enviable selection of chic, inexpensive accessories—I wanted all of the shoes and jewelry. What impresses me most about The Mall at Millenia is how it’s home to so many of the stores I love to shop at, like Abercrombie & Fitch, LOFT, Forever 21, Urban Outfitters and Macy’s, which means I can knock out all of my preferred shopping spots in one sweep. I also couldn’t help but venture into Gucci for a look inside— the store is huge compared to other Gucci locations I’ve been to, and the associates were just as welcoming and as colorful as the storefront!

For refueling purposes, there are two Starbucks Coffee locations inside the mall (the one on Level 2 is the best bet for shorter lines). And when a little break from shopping was needed, I really enjoyed spending time in Grand Court, taking in the sights and sounds around me—I definitely recommend that you take a moment to do the same!

Saturday, 3 p.m.—The Fountains at ChampionsGate

Following a quick bite to eat for lunch, I checked in to the vacation rental I’d booked, a gorgeous 3-bedroom, 2.5-bathroom townhouse at the Fountains Resort at ChampionsGate. When it comes to accommodations, I’m the hotel patron that always puts the “Do Not Disturb,” sign on the door handle and leaves it there, because once I’ve nested, I don’t want anyone coming in to tidy up my stuff. I value my privacy, so when it came to booking my stay, I thought it’d be interesting to try a vacation rental this time around, and I’m so glad that I did!

Nestled away in a beautifully landscaped and gated community, my townhouse was truly a home away from home. Nightly rates are comparable to that of a hotel, but the best part is, these townhomes provide a comforting stay for up to 10 people, ideal for family reunions or even a fun trip with friends.

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Sunday, 10 a.m. —Celebration Farmer’s Market

The early bird definitely gets the worm when it comes to the Celebration Farmer’s Market, which occurs every rain-free Sunday from 9 a.m. to 2 p.m. just outside of Celebration Town Center. I’d never been to this area before, and I can’t believe all that I’ve missed out on! There are tents all around, featuring homemade edibles, décor, and fresh produce. I admittedly went a little wild at the market, buying some freshly-made guacamole, chicharrones, and a package of chipotle habañero beef jerky.

Sunday, 12 p.m. —Holler and Dash Biscuit House

Even after all the snacking that happened at the farmer’s market, I was still ready for a full meal, and thought I’d check out the brunch spot that everyone recommended to me: Holler and Dash Biscuit House. My, oh, my, did this place delight, with bold, aromatic coffee brews and soft, fluffy biscuits topped with all the sweet and savory combinations you can think of. I opted for the Andouille Hustle: an open-faced biscuit surrounded by flavorful house-made sausage gravy and piled high with Andouille sausage, cheddar cheese and scallions on top. It was incredibly tasty and filled me up quick!

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Sunday, 4 p.m.—Disney Springs

After a short siesta at the townhouse, I headed to Disney Springs, my favorite spot for a combined eating and shopping experience. If I’m being completely honest, I love Disney Springs even more for its efficient parking system—trying to find a parking spot before embarking on a shopping adventure has never been so stress-free!

Disney Springs is a welcome experience for its visitors, offering plentiful, unique options for both dining (Morimoto Asia, STK, The Polite Pig) and shopping (Uniqlo, SuperDry). Immediately upon arrival, I had to stop at the two-story Zara, and left the store with an incredibly comfortable, vertically-striped T-shirt that has since proven perfect for both dressing up or down. I also took the time to explore Uniqlo and immediately understood why they are the innovative casual-wear retailer—the store itself was enamoring and there were so many beautiful pieces inspired by artistic collaborations with designers and artists from around the world.

Disney Springs is like a theme park of its own, with plenty of ground to discover—to say that the area is expansive is an understatement. With every turn, there’s something exciting to partake in: one minute, I’m witnessing the launch of an amphicar, with kids and their parents watching along in awe—the next minute, I’m grooving along to live music happening just outside of Starbucks Coffee.

After purchasing a caramel apple at the Candy Cauldron to indulge in later, I assessed my choices for dinner and opted to try The Edison, a relatively new, steampunk-themed restaurant. The interior was intricately designed and adorned with 1920s antiques, the perfect setting to unwind over delicious cocktails and dishes. The DB ‘Clothesline Candied Bacon’ was the showstopper of the night and is a must-order, served with both maple and black pepper sauces and a side of sliced sour pickles.

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Monday, 10 a.m.—Orlando Premium Outlets, International Drive

I got up bright and early Monday morning to take a special tour of the Orlando Premium Outlets on International Drive, which are my favorite outlets because of the Victoria’s Secret, Express, and American Eagle Outfitters stores. The Orlando Premium Outlets on International Drive features an eclectic mix of designer and exclusive-to-market retailers that cater to both international and local visitors, at 25-65% off.

I love the open feel of Orlando Premium Outlets—vaulted skylight ceilings and open roof areas mix consecutively throughout, allowing for plenty of beautiful Florida sunshine to brighten and enhance your shopping trip. The paved brick walkways add a familiar, leisurely pep in your step, with a beautiful bridge that connects one shopping experience from one half of the mall to the other.

My first stop whenever I’m at the Orlando Premium Outlets is Coach—I never want to miss out on the opportunity to snag the cutest bag at an incredible deal. More often than not, there’s always a coupon that’s offered at the door for even more savings. And the Victoria’s Secret Outlet is not to be missed during your visit—but be prepared, because the store is always crowded!

Pro Tip: Florida residents can stop by the Management Office and show their license for a free valet parking pass and a reusable shopping bag filled with coupons for even more savings—this is super handy if you get caught in mid-day outlet traffic and don’t want to scramble to find a parking spot!

Admittedly, I didn’t want to leave—three days wasn’t enough to fully shop and eat to my heart’s content, so I’m already planning my next extended weekend trip!

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