Holiday houses in Kissimmee
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Top-rated holiday rentals in Kissimmee
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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.
Getaway w/ Game Room + Pvt Pool | Solara
Welcome to our single-family home inside the prestigious Solara Resort in Orlando, the perfect getaway for families and friends seeking both comfort and excitement. This spacious 5-bedroom, 4.5-bathroom retreat features modern décor, a fully equipped kitchen, a cozy living and dining area, and a private pool with SPA for endless fun under the Florida sun. Guests will also enjoy a game room in the garage and a stylish loft with TV, making it an ideal spot to relax after a day at the parks.
Family Home w/ BBQ, 7 Min from Disney, Accessible
Welcome to our luxurious vacation home Magic Village Views, located only 3 miles (5 km) from the renowned Disney Parks! Our serene single home is situated in a modern gated community, offering a comfortable retreat in the heart of Orlando, with top-notch amenities, including sleek stainless steel kitchens, tasteful furnishings, and a well furnished private patio. In addition, we have taken great care to ensure that our home is fully accessible to guests with special needs.
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!
Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.
House by the Mouse: Something for Everyone!
Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!
The Eights House by Disney. Themed Island Dream
Location can't get better! Next to Disney Parks and Restaurant Row! This Guarded and gated place to stay is perfect for family trips. You will fall in love with our year round 12ft tree tastefully decorated by season. Mickey's Camping room, Frozen themed room, the cabin Christmas year round experience & 2 additional modern king rooms perfect for couples! Did I mention the stunning Avengers Home theater/game room and oversized pool?
NEW Luxury 6Bedrooms At Encore Resort
The Space * Accommodates: 15 * Bedrooms: 6 * Bathrooms: 5 * Property type: Luxury House * Location: Encore Resort - Close to: * 8 miles from Disney * 13 miles from SeaWorld * 11 miles from Outlet Premium * 23 miles from Florida Mall * 25 miles from MCO * Located near 415, 429, I4, our house is in the heart of Kissimmee, close to restaurants, pharmacies and market.
Newly Renovated Luxury Villa| Pool Table &Foosball
Enjoy the perfect getaway at our Luxury Villa! Perfect for families!—just 9 miles from Disney! - Accommodates 12 GUESTS - 5 EN-SUITE - Floor-to-ceiling blackout curtains - New garage GAME ROOM w/ POOL TABLE & FOOSBALL - Large backyard with outdoor shower - Private heatable pool & whirlpool spa - Mickey Mouse-Themed Bedroom -Dedicated Workspace - Smart TVs
Family 3BR at Lake Berkley Resort
Find the perfect balance of comfort, convenience, and fun in this charming 3bedroom, 2.5bathroom townhome, located in Lake Berkley Resort, one of Orlando’s most desirable gated communities. Just 15 minutes from Walt Disney World, this home is ideal for families and groups looking to enjoy the best of Orlando while staying in a peaceful, resort-style setting.
Minutes to Disney Villa with pool
Your family will be close to everything when you stay at this newly remodeled villa. Enjoy large pool deck with pool and entertainment room. TV's with Disney+, high speed internet, espresso machine and other high end kitchen amenities.
3 Bedrooms/ 2.5 Bathrooms At Reunion! (7635)
• Resort: Reunion • 3 Bedrooms/2.5 Bathrooms/Sleeps 10 • Disney (15 min) Sea World (20 min) Universal (25 min) • Convention Center (25 min) Legoland (40 min) • Location: Heritage Crossing Way, Kissimmee FL 34747
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
4 Season Vacay, Near Disney, King Bed ste
Lakeside paradise
Modern King Apt w Water view, Pool Gym Near Parks
Mickey’s Lakeside Villa w/ pool near Disney!
Think Pink 2BR • Pool, Free Park, Priv Patio, Gym
Private Pool Townhome • 10 Min Disney • Sleeps 10
3BR Margaritaville Resort Townhouse, Close to WDW!
7458A Magic Village 9 guests jacuzzi 8 min Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $199 AUD | $205 AUD | $214 AUD | $208 AUD | $184 AUD | $195 AUD | $207 AUD | $181 AUD | $167 AUD | $175 AUD | $198 AUD | $233 AUD |
| 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.
Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,330 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at $28 AUD per night before taxes and fees
Verified guest reviews
Over 262,660 verified reviews to help you choose
Family-friendly holiday rentals
6,190 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 1,210 rentals that welcome pets
Holiday rentals with a pool
6,620 properties feature pools
Rentals with dedicated workspaces
4,060 properties have a dedicated workspace
Wi-Fi availability
7,280 of Kissimmee holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Gym 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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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Give Kids the World Village
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Shingle Creek Golf Club
- Universal's Islands of Adventure