Romantic Kissimmee Weekend Getaway Guide

Feeling a cozy vacation home for your Kissimmee stay? Or maybe an inclusive resort experience? We’ve got accommodations for every style and budget that you’ll both love.

A Condé Nast “Top 200 Hotel,” settle in for some time together at this iconic hotel that combines classic elegance and turn-of-the-century charm on the edge of tranquil Lake Rianhard in Celebration Town Center. Stroll or ride a bike through the town, originally developed by the Walt Disney Company, and return to enjoy an evening swim at the hotel’s pool.

For when you want to indulge, soak in all this tropical-inspired paradise has to offer with a championship golf course, separate adult pools and spaces, and seven on-site restaurants. Grab a cocktail and float away the day in a 850-foot lazy river.

From one-bedroom suites to mega mansions that'll have you living your movie star fantasy, Jeeves Florida Rentals offers all kinds of options for a romantic escape. Think crackling fire pits, in-house movie theaters, and cool infinity pools.

Want all the amenities of a resort with the privacy of a vacation home? Then Magic Village Yards is the place for you two! Spend a relaxing night in and make dinner together at your home’s outdoor summer kitchen, then watch the sunset from a bubbling Jacuzzi.

After some downtime, add some thrill to your couples’ long weekend with adventurous activities to add a spark to your Kissimmee vacation.

These views are worth waking up for. Nothing says romance more than raising a glass of champagne from 1,000 feet up on a breathtaking flight in a hot air balloon over Central Florida. Soak in views of lush natural landscapes and spot a few theme parks along the way.

Ready for a real leap of faith? Head to Gatorland and soar 65 feet in the air above Cuban and Nile crocodiles before flying over the alligator breeding marsh where 130 gators are hanging out below.

From happy penguins and sea turtles to pink flamingos and bottlenose dolphins, this is the perfect place for animal lovers. Get up close with playful porpoises at Dolphin Cove, then — for a little extra adventure — challenge your partner to ride Mako_®, Orlando’s tallest, fastest, and longest coaster.

Dance to the sounds of sultry blues music at the House of Blues at Disney Springs®. Enjoy free live tunes in the courtyard every night of the week, plus big ticket shows to make for a memorable night out.

To perfectly balance a day full of thrills, plan time to chill with relaxing moments that let you enjoy some quality time together. 

Saddle up for a spur-of-the-moment date! Enjoy serene scenes while riding beautiful horses through winding trails along the Kissimmee Valley — passing by hundred-year-old oak hammocks and the shore of Lake Tohopekaliga.

Stop by Le Macaron French Pastries and treat your sweetie to some sweets! Choose from macarons and gelato in both classic and inventive flavors including bubble gum, rose, and lemon cream. Order to go, have a picnic along the edge of Lake Rainhard, and watch the world go by.

Kissimmee locals know Vivian’s is a hidden gem for spa goers looking to indulge in total relaxation. If you’re short on time, they offer amazing 30-minute express services, but to really treat yourselves, we suggest the luxurious Spa Serenity Package.

For whatever you’re craving, you’ll find wow-worthy Kissimmee dining experiences that are sure to set the mood.

Whether you need something to go with dinner at your vacation home, or you’re simply in search of a new favorite, the fruit wines at Formosa Winery Tasting House pair with just about everything. Stop by for Saturday or Sunday brunch and sip sangria and mimosas as you stroll through the vines.

This family-owned local favorite is sure to add just the right amount of spice to date night. With authentic Thai decor and fresh, bold flavors, start with the Thai Sampler to share and sip creamy Thai iced tea.

Modern style meets the electric energy of a 1950s Havana nightclub at this celebrated restaurant owned by Gloria and Emilio Estefan. Try a sizzling steak and fresh, fruity mojitos, and enjoy the bustle of the Promenade at Sunset Walk.