By Abigail Bass
September 4, 2026
It’s the most wonderful time of the year again, and there’s no better way to celebrate than with that special someone.
As the streets of The City Beautiful begin to glow with festive holiday cheer, now’s the perfect time to plan your next holiday date night in Orlando.
Whether you’re looking for lighthearted fun or a one-of-a-kind dining experience, there are plenty of romantic things to do in Orlando. And when you choose Rosen Plaza for your holiday getaway, you’ll be in prime position to enjoy them all.
Ready to experience holiday magic in The City Beautiful? Here’s our list of Orlando holiday date ideas to make the most of this uniquely special time of year.
Key Takeaways
- Celebrate the Holidays at Rosen Plaza
- Share a Meal at Jack’s Place Restaurant
- Go on an Ice Skating Date
- Look at Christmas Lights
- Watch a Holiday Show Together
Celebrate the Holidays at Rosen Plaza
There’s no better way to complete your Orlando holiday date night than with a romantic stay in the heart of the city.
At Rosen Plaza, our comfortable and stylish accommodations are ideal for creating magical memories with your special someone. And with a convenient I-Drive location, you’ll never be far from the best holiday couples activities in Orlando.
If you’re in town on December 24 or 25, savor the best festive dining in Orlando with our Christmas Eve and Christmas Day dining experiences. Check back soon to discover the extraordinary flavors that await you and your partner this year.
Let our heartwarming team at Rosen Plaza help make your seasonal celebrations extra special by booking your stay today.
Share a Meal at Jack’s Place Restaurant
While there are countless ways to celebrate the holidays as a couple in Orlando, sharing a delicious meal together will always be a timeless tradition.
Jack’s Place, widely known as the best steakhouse on I-Drive, welcomes all couples looking to savor festive dining in Orlando with sensational flavors and a charming ambiance. The restaurant’s soft amber lighting and signature steak dishes create the perfect environment for rekindling that special spark during the holidays.
Taste the flavors of Florida with freshly prepared seafood including herb crusted salmon or indulge in your choice of tender steak made from the finest ingredients. If you’re spending Christmas Eve in Orlando, enjoy an elegant, three-course prix fixe dinner during Christmas Eve at Jack’s Place.
Go on an Ice Skating Date
During the holidays, simple moments like bundling up and holding hands with your partner feel extra special.
Ice skating as a couple is a great way to cherish these ordinary moments by adding a touch of wintery wonder to your Orlando holiday date night.
While warm temperatures linger early in the holiday season, ice skating offers the perfect seasonal cool down. A variety of ice skating rinks throughout the city also make it one of the most popular couples activities in Orlando.
Skaters of all skill levels can glide over to the Ice Factory of Central Florida, where public skating is available all throughout the week. Couples can also lace up their skates at Orlando Ice Den, where holiday-themed events take every date night to a cool new level.
Look at Christmas Lights
While trees in Florida may not be covered in snow, they are decked out in plenty of dazzling decor for the holidays. And there’s no shortage of Orlando holiday lights waiting to be enjoyed with your significant other.
Harry P. Leu Gardens, north of downtown Orlando, transforms its 50 acres into an enchanting wonderland during their annual Dazzling Nights event. See giant crystal chandeliers hanging from treetops and stroll through a magical meadow filled with lit-up fireflies and butterflies.
Each year, the beloved Christmas Tree Stroll at Disney Springs welcomes a unique lineup of brightly decorated Disney-themed Christmas trees, including ones inspired by Pixar, Star Wars, and superhero favorites.
Watch a Holiday Show Together
If bonding over the arts is more you and your partner’s style, watching a live show together is a uniquely festive way to spend a Christmas date night in Orlando.
Make your romantic holiday evening unforgettable with performances that can only be seen during this magical time of year.
In the heart of downtown Orlando, discover a lineup of festive holiday performances at the Dr. Phillips Center for the Performing Arts. Share a romantic evening with your partner by watching beautiful depictions of The Nutcracker or listening to the seasonal sounds of talented artists performing special holiday-themed songs.