Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Cozy Condo Only 6 Minutes From Disney World
Step into our inviting condo, where coziness embraces you! Our charming property is strategically located only 6 minutes from the Theme Parks, prestigious Outlets, and excellent Restaurants. Experience the comfort of having ample space for up to 5 guests, with a King Size bed in the suite and a Twin-Full Bunk Bed available. Experience luxury living with our high-quality furniture and decor. Our Condo is fully equipped with a modern open-style kitchen and appliances, high-speed WiFi 5G, Cable
Magic Getaway | 4 En-suites, BBQ & Near Parks
Welcome to your dream getaway at Magic Village Views — just 3 miles (5 km) from the magic of Disney! This private villa offers a refined and comfortable retreat in the heart of Orlando, just minutes from the city’s most iconic attractions. Enjoy premium amenities such as a modern stainless steel kitchen, a private BBQ grill, and sophisticated décor designed for both relaxation and style. Each bedroom features its own TV and en suite bathroom, ensuring privacy and convenience for all guests.
Magical Stays Near Disney
✨🏰 Magical Disney Escape 🏰✨ Stunning 4BR/3BA home with 2 kings, 1 queen, 2 twins & huge L-shaped couch! 🌟 Splash in your private pool, relax on the lanai, or battle in the Star Wars glow-in-the-dark game room 🎮. Enjoy board games, movies, and smart TVs with Netflix/HBO/Amazon 📺. Newly renovated kitchen & in-house washer/dryer 🧺. Minutes from Animal Kingdom, Disney Springs & all parks — perfect for families & groups! 🎢✨ Free WiFi, parking, and all the magic you need!
6BR Oasis w/ Private Pool, Game Room & Lanai
Escape to luxury in this stunning 6-bedroom home featuring a private pool and a fully equipped game room. Conveniently located just 15–20 minutes from Walt Disney World and within easy reach of Universal Studios, SeaWorld, shopping, dining, and golf, this home puts you right in the heart of Central Florida’s top attractions—while still offering a peaceful retreat. Perfect for families, groups, or your next unforgettable getaway—comfort, fun, and relaxation all in one place.
Luxury Townhouse Near Disney | 3BR
Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!
Lush Green Retreat 10 Min to Parks Pets Allowed
Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY
Jacuzzi Magic Village 4 suites near Disney & 192
MAGIC VILLAGE VIEWS - 8 GUESTS - 4 SUITES - BBQ - JACUZZI - 06 MIN DISNEY Magic Village Views, new condominium, with houses of modern contemporary architecture, rooms with double height ceilings, contemporary furniture, terrace with barbecue and parking spaces in front of the unit. Well located near US-192, 6 minutes from Disney parks, 25 minutes from Universal, 26 minutes from Sea World, 3 minutes from pharmacies and Walmart. (3081 Rcf way)
Villa w/ Pvt Pool & BBQ + Resort | 10 min Disney
Welcome to your dream vacation home! Ideally located in Emerald Island Resort, this stunning 3-bedroom, 2-bath villa offers comfort, space, and privacy for the perfect Orlando getaway. Enjoy an open-concept layout, a private pool with BBQ grill, and a cozy workspace for added convenience. Just minutes from Walt Disney World, restaurants, and shops, this home combines luxury, relaxation, and resort-style amenities for an unforgettable stay!
Modern 3Bed Townhouse in the Heart of Reunion 772
Welcome to Our Stunning 3-Bedroom townhouse – Perfect for Families & Groups! Experience luxury, comfort, and top-tier hospitality in our brand-new 3-bedroom, 2.5-bathroom townhouse, designed to accommodate up to 6 guests. Whether you're planning a family vacation or a getaway with friends, our spacious retreat has everything you need for an unforgettable stay. Prime Location at Reunion Resort, just a few miles from the Disney area.
Twist of Lime Cottage in Margaritaville nr Disney
Welcome to your own island-inspired oasis. Our charming cottage "Twist of Lime" is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.
No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!
**We offer a FREE EV Charger! We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.
Private Pool Home Near Disney | 4BR Sleeps 10
Modern designer home with private pool, perfect for families and groups near Disney. Sleeps 10 in 4 stylish bedrooms and features a chef-style quartz kitchen, elegant dining for 8, spacious living area, and a fun kids’ room. Located in a quiet upscale community just 20–25 minutes from Disney, with easy access to Universal and Orlando’s top attractions.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Pool+Game Room 10 min to Disney sleeps 10
Luxury Villa with Private Pool Near Disney World
House near Disney in Davenport FL
Encore Themed Retreat
Sunkissed Oasis 5 BR Home, Pool, Spa & Game Room
Brand-New Renovated 5BR Home at Storey Lake
Spacious townhome near Disney w/ patio
Fully refurbished 5BR/5BA Villa w/ private theater
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £111 | £115 | £123 | £109 | £97 | £103 | £109 | £95 | £88 | £92 | £104 | £123 |
| 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.
Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,260 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at £15 per night before taxes and fees
Verified guest reviews
Over 267,190 verified reviews to help you choose
Family-friendly holiday rentals
5,840 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,160 rentals that welcome pets
Holiday rentals with a pool
6,460 properties feature pools
Rentals with dedicated workspaces
4,030 properties have a dedicated workspace
Wifi availability
7,170 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
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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field