Holiday rentals in Kissimmee
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,040 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at £7 per night before taxes and fees
Verified guest reviews
Over 277,640 verified reviews to help you choose
Family-friendly holiday rentals
5,830 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,120 rentals that welcome pets
Holiday rentals with a pool
6,330 properties feature pools
Rentals with dedicated workspaces
3,970 properties have a dedicated workspace
Wifi availability
6,950 of Kissimmee holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Lake access across Kissimmee rentals
4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
150 Inch 4K Movie Theater Pool & Spa sleeps 16
"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.
Haven Luxury
Welcome to Haven Luxe – A Cozy Retreat with a Touch of Elegance Escape to a sanctuary where comfort meets sophistication. Haven Luxe offers an inviting blend of warm ambiance and upscale design, perfect for travelers seeking both relaxation and style. Sink into plush velvet furnishings, Whether you're savoring morning coffee by the pool, or cozying up with a book inside. 5 min from brightline train station and (MCO) Airport. 20 minutes from Theme parks. 2 from Publix, Walmart, CVS, shoppes
Near Disney | Heated Pool, King Bed, Arcade
✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!
10 Minutes to Disney King Bed, Heated Pool, Arcade
✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!
4BR Disney & Universal Themed Villa Reunion Resort
Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.
12BR Disney Beach house| Pool, Theater, Arcade
Stay near Walt Disney World in this luxury 12-bedroom Orlando vacation home, perfect for large families and groups. Enjoy a private pool and hot tub, movie theater, Transformers game room, poker table, outdoor kitchen, and themed Minions, Moana, Scooby-Doo, Inside Out, and Lilo & Stitch bedrooms. With multiple king suites and space to relax, play, and reconnect, it’s the perfect Disney-area getaway for reunions and unforgettable group vacations.
Near Disney • 4BR • Perfect for Families
Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!
Montego Bay Retreat | 15 Min to Disney
Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨
Disney's Pool House
Magical family retreat in Central Florida! Just minutes from Disney, this spacious home features fun Disney-themed decor, a private screened pool, game room with pool table and air hockey, smart TVs, full kitchen, free Wi-Fi, and washer/dryer. Close to Universal, SeaWorld, CityWalk, and International Drive—perfect for families looking to relax, explore, and create unforgettable memories in the heart of all the action!
Disney area 4-bedrooms spacious villa for rent
Our villa offers a pleasant and relaxing place for families at an affordable price. Rent a private villa with a gorgeous swimming pool in a family-oriented residential neighbourhood. It has an excellent conservation view and outdoor space with a small pond. This home is in Eagle Point, Poinciana Blvd. in Kissimmee, near the Walt Disney World Resort.
Disney Theme Rooms | Private Pool | Storey Lake
Welcome to your dream vacation at Storey Lake, one of the most loved resorts by travelers visiting Orlando. This beautifully designed 4-bedroom, 3-bath townhome was created to bring comfort, fun, and unforgettable memories all in one place, just minutes from Disney and the area’s top attractions.
15 Bd/ 16.5 Ba/ Sonoma Resort (4011 Sb)
• Community: Sonoma Resort • 15 Bedrooms/ 16.5 Bathrooms/ Sleeps 42 • Disney (8.5 miles) SeaWorld (10.0 miles) Legoland (36.6 miles) • Convention Center (11.9 miles) Universal Studios (15.7 miles) • Location: Sonoma Blvd, Kissimmee FL 34746
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Epic stay at Vista Cay!
Brand new luxury near clubhouse / lake view (405)
6BR Home w/ Priv Pool Near Disney Gated Resort
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
Orlando Dream Escape | Private Pool | Disney
2026 Themed NEW 08 Bedrooms At Solara Resort
Luxe Family Retreat | Pool Villa Near Disney & MCO
Haunted Mansion-inspired Ghoulish Sanctuary
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £110 | £115 | £122 | £125 | £107 | £110 | £108 | £95 | £87 | £92 | £104 | £122 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Kissimmee?
Kissimmee has accommodations in resort areas near theme parks, private homes around Reunion and Storey Lake, and family-friendly neighborhoods with easy access to local attractions. Many spaces feature pools, spacious layouts, and outdoor amenities for group stays.
What are the best things to do in Kissimmee with kids?
Families can explore fun attractions like Gatorland, ride thrilling coasters at Old Town, or enjoy large playgrounds and splash pads in city parks. Themed entertainment and interactive experiences are frequently suggested for younger visitors.
What are some of the best things to do in Kissimmee?
Discover live shows and rides at Old Town, visit Gatorland for wildlife encounters, or explore regional history at the Osceola County Historical Society. The area is also known for airboat tours and vibrant outdoor markets.
How is the weather in Kissimmee?
Kissimmee has mild winters around 49–72°F (10–22°C) and hot, humid summers reaching 74–92°F (23–33°C) with frequent rainfall from May through September. Lightweight clothing, sunscreen, and a rain jacket are recommended.
What are the best places to visit in Kissimmee?
Popular places include Old Town for entertainment and shops, Gatorland for reptile encounters, and the Kissimmee Lakefront Park with walking trails and playgrounds. Museum enthusiasts will often find exhibits at local historical centers.
What are some hiking trails in Kissimmee?
Stroll boardwalks and shaded paths at Shingle Creek Regional Park, walk lakeside trails at Kissimmee Lakefront Park, or explore nature preserves nearby. Trails often highlight local wildlife and peaceful scenery.
What are some family activities we can do in Kissimmee?
Explore Gatorland’s exhibits, ride classic attractions at Old Town, or play in the splash pads at Kissimmee Lakefront Park. Family-friendly dining spots and arcades are also popular choices for shared outings.
What are some of the best day trip ideas from Kissimmee?
Explore Orlando’s theme parks, stroll nature reserves around Lake Tohopekaliga, or enjoy coastal beaches for a change of scenery. You can also visit nearby state parks or experience local wildlife tours.
Are there any pet friendly accommodations available in Kissimmee?
Many Kissimmee neighborhoods, including those near Central Kissimmee and the resort communities, have pet-friendly vacation rentals. Parks and outdoor spaces throughout the area make traveling with pets convenient.
What are some local tips for visiting Kissimmee?
Hydrate frequently in warm months, and bring insect repellent for outdoor activities near lakes. Book popular attractions in advance and explore local eateries for regional flavors beyond the main tourist areas.
What is Kissimmee known for?
Kissimmee is known for its proximity to major theme parks, distinctive wildlife experiences like Gatorland, and vibrant entertainment districts such as Old Town. Airboat rides and access to lakes add an outdoor adventure element.
What are the best hidden gems to explore in Kissimmee?
Visit Shingle Creek Regional Park for quiet paddling and wildlife spotting, shop local at farmers markets, or discover history at the Osceola County Historical Society museum. Neighborhood spots often have authentic flavors and art.
What are the best foods to try in Kissimmee?
Enjoy Southern-style barbecue, fresh seafood, and Latin flavors like Cuban sandwiches or empanadas at locally rooted eateries. Homemade ice cream and citrus-inspired desserts are frequently suggested, especially in summer.
What should I bring for a trip to Kissimmee?
Pack lightweight clothing, sunscreen, and a hat for sun protection. A rain jacket, comfortable walking shoes, and insect repellent are useful for exploring parks and outdoor attractions.
What is the nightlife in Kissimmee like?
Kissimmee has lively spots for live music, themed bars, and outdoor events in areas like Old Town. Nighttime entertainment often includes family-friendly shows and locally owned restaurants with late-night menus.
What are the most popular events or festivals in Kissimmee?
Kissimmee hosts car shows, holiday parades, and cultural festivals around Old Town, with seasonal fairs and outdoor concerts often taking place in parks. Late spring and holiday weekends feature many community gatherings.
Are there family friendly vacation rentals in Kissimmee?
Family-friendly vacation rentals are available throughout Kissimmee, particularly in resort-style neighborhoods and private home communities. Many have amenities like pools, recreation rooms, and easy access to parks and attractions.
When is the best time to visit Kissimmee?
Late autumn and early spring are often recommended, with milder temperatures and smaller crowds. Summer brings lively local events and frequent afternoon rain, while winter stays mild and sunny.
All about Kissimmee
Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.
What are the top things to do in Kissimmee?
Old Town
Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.
Fan Boat Swamp Tour
Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.
Hot Air Balloon Ride
Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Epcot
- Universal's Volcano Bay
- Kia Center
- Camping World Stadium
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure