Kissimmee Holidays

Kissimmee is a small town on the outskirts of Orlando (perfectly positioned for Walt Disney World), where villa-style resorts and neon Americana meet real Florida cowboy country. Do the parks by day, then come home to funnel cakes, classic cars and a pool a few steps from your door.

Highlights of your Holidays to Kissimmee

• Disney on your doorstep - Kissimmee sits right up against the Walt Disney World gates, closer than most of Orlando itself, with Universal and SeaWorld an easy drive up the road

• Space to spread out - This is townhome and villa-resort country: kitchens, separate bedrooms and resort pools, built for crews who've outgrown a single hotel room

• Old Town - A walkable slice of vintage America with fair rides, sweet shops and a famous weekly classic-car cruise that takes over the main street

• Proper cowboy country - Kissimmee was a cattle town long before the Mouse arrived, and the Silver Spurs Rodeo still packs the arena twice a year

• Swamp adventures - Airboats skim Lake Toho's marshes from the edge of town, all gators, herons and big-sky Florida

• Waterpark weather - Island H2O's slides and lazy river are minutes from most resorts, made for the day the parks can wait

Good to Know

• ☀️ Weather - Warm all year: low 30s°C through summer with sunshine most days, low-to-mid 20s in winter, and the odd spectacular afternoon storm that clears in time for the pool

• 💰 Money - Cards everywhere; a casual sit-down meal runs £15-£20 / €17-€23, a beer is £5-£6 / €6-€7, and many resorts add a nightly resort fee of £14-£24 / €16-€28 at check-in

• 🏛 Fun Fact - Downtown Kissimmee hides one of America's oddest roadside landmarks: the Monument of States, a tower built in 1943 from rocks posted in by every US state

Kissimmee is perfect for you if...

• You're doing Disney and you want something better value than international drive, but still just minutes from the gates, not half an hour down a motorway

• You need holiday-home space (a kitchen, doors you can close on the kids) with resort pools thrown in

• You secretly want to watch a real rodeo between waterpark days

• You're travelling as a big multi-generation crew and one hotel room was never going to cut it

🏨 Hotels

Kissimmee does places to stay differently: townhomes with kitchens, villa resorts with waterparks and value hotels minutes from Disney's gates. Whatever the size of your crew, there's a fit here. See all hotels in Kissimmee.

👨‍👩‍👧‍👦 What are the best family hotels in Kissimmee?

• Encantada Resort is the family favourite: two to four-bedroom townhomes with kitchens and multiple bathrooms, so mornings don't start with a queue for the shower.

• Hilton Vacation Club Mystic Dunes Orlando spreads suites with kitchenettes across leafy grounds with four heated pools, mini golf and a kids' activity hub, plus shuttles for the Disney days.

• Hilton Vacation Club Polynesian Isles Kissimmee brings tiki-flavoured fun with rooms built around kitchens and patios, and a choice of freshwater or saltwater pools that settles the daily debate.

🎉 What are the best hotels in Kissimmee for groups?

• Westgate Vacation Villas Resort & Spa is a small town of villas about a mile from Disney with fourteen pools and hot tubs, a waterpark and a spa, big enough that nobody's arguing over sunbeds.

• Legacy Vacation Club Orlando does suites sleeping up to eight, the simple answer when the group chat says "let's all just stay together".

• Baymont by Wyndham Orlando Lake Buena Vista South keeps a crew fuelled with a free buffet brekkie of eggs, bacon and waffles, plus a pool with a kids' area for the non-park days.

💰 What are the best value hotels in Kissimmee?

• Ramada Kissimmee Gateway packs in two pools, mini golf, an arcade and a smokehouse grill, so the budget stretches without the holiday feeling like it did.

• Comfort Suites Maingate East does roomy suites, a heated pool and a free hot breakfast, minutes from the Disney gates.

• Westgate Towers Resort keeps it simple with a pool, a dedicated kids' pool and arcade games, a solid base that saves the spending money for the parks.

👉 All hotels in Kissimmee

Cheap holidays to Kissimmee

Kissimmee is where an Orlando-area holiday gets seriously good value. Townhomes and suites with kitchens mean breakfasts in, packed lunches for park days and a supermarket run doing the work of three restaurant bills, and several value hotels throw in free hot breakfasts on top. When you're comparing prices, add the nightly resort fee of £14-£24 / €16-€28 that many resorts charge at check-in, so you're always comparing the true cost.

The town keeps the fun cheap too. Old Town is free to wander (you pay per ride, not at a gate), the weekly car cruise costs nothing to watch, lake sunsets are free every single evening, and the resorts' own pool complexes can swallow a whole day without a ticket in sight. Multi-day theme park tickets cost far less per day than singles, so settle the park plan before you buy.

Book early for school-holiday dates, when the Disney-doorstep resorts fill first, and keep an eye on low-deposit deals so the upfront cost stays small while the budget goes on the fun.

Kissimmee Holidays 2026/2027 - Travel Guide

👨‍👩‍👧‍👦 What are the best things to do on a Kissimmee family holiday?

• Walt Disney World - The main event, and the reason Kissimmee exists in its modern form: four parks and two waterparks, with the gates just minutes from the Maingate resorts

• Old Town - Free-entry Americana with fair rides, a Ferris wheel, sweet shops and funnel cake, the easiest great evening in town

• Island H2O Water Park - Slides, a lazy river and a wave pool minutes from the resorts, the perfect between-parks day

• Gatorland - Old-Florida gator wrestling, a breeding marsh boardwalk and zip lines over the toothy residents

• Boggy Creek Airboat Adventures - An hour skimming Lake Toho's marshes spotting gators and eagles, pure Florida showing off

💑 What are the best things to do for couples on a Kissimmee holiday?

• Sunrise balloon flight - Hot air balloons lift off from Kissimmee at dawn and drift over the lakes and parks, a properly special start to a day

• Celebration - The picture-book town Disney built next door, made for a lakeside stroll, a long lunch and a very good bakery stop

• Promenade at Sunset Walk - The strip's newest evening spot: live music, cocktail bars and restaurants that stay lively late

• Lake Toho at sunset - Grab a bench at the lakefront park downtown and watch the sky go full Florida, no ticket required

🎉 What are the top things to do for groups on a Kissimmee holiday?

• Medieval Times - Jousting knights, falconry and a feast you eat with your hands, the dinner show your group will quote all week

• Silver Spurs Rodeo - One of the biggest rodeos in the eastern US, with 2026 editions in June and October, bulls, barrels and big cowboy energy

• Old Town's weekly car cruise - Hundreds of classic American cars rolling down the main street with rock and roll on the speakers

• Fun Spot America Kissimmee - Go-karts on multi-level tracks, old-school coasters and arcade bragging rights, open late

More Destinations

• Orlando - The theme park capital of the world: Walt Disney World, Universal, world-class waterparks and a different character breakfast every morning

• International Drive - Orlando's big-fun strip: 11 miles of attractions with Universal at one end, SeaWorld at the other and a 400ft observation wheel in the middle

• Florida - The Sunshine State in full: Orlando's parks, Miami's beaches, Gulf coast white sand and Everglades airboats

• Miami - Art deco glamour, Cuban coffee, golden sand and a nightlife scene that never got the memo about bedtime

• Las Vegas - Neon, mega-resorts, world-famous shows and the Grand Canyon within day-trip distance, the other great American playground