Holiday rentals in Kissimmee
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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 $13 SGD 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.
New! Epic Dream House with Pool
Enjoy epic opening rates! Make some memories at this uniquefamily-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles away from Disney's exit & parks.
Luxury Retreat at Reunion Resort
Luxury Retreat at Reunion Resort – 12 Miles from Disney! Welcome to our stunning vacation home nestled in the prestigious Reunion Resort! This elegant getaway offers the perfect blend of luxury, comfort, and convenience, making it an ideal retreat for families and groups. The home offers a beautiful back yard pool and spa area for you to enjoy, while playing music through the surround sound system in the house and in the back yard. EV Friendly. With 6 Bedrooms You wont regret staying here.
Haunted Mansion-inspired Ghoulish Sanctuary
Welcome, Foolish Mortals... To the Ghoulish Sanctuary: An immersive Haunted Mansion-themed stay just 15 minutes from Walt Disney World, where candlelights flicker, and the air is deathly still... Experience a one-of-a-kind Haunted Mansion-themed stay for up to 6 people. This spooky rental in Kissimmee lets you inhabit your favorite ghostly estate... if you dare. Ready to play your next campaign and need a place to gather for your DnD weekend? The sanctuary and its spirits await.
10 Min to Disney | Kings | Heated Pool | Games
✨ 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!
ChampionsGate Villa: Pool, Golf Theater & F1
Experience one of ChampionsGate's most unique vacation homes. This luxury 6-bedroom villa features a golf-themed theater, Formula 1 game room, Mandalorian bunk room, Spider-Man bedroom, private pool & spa, and complimentary ChampionsGate Resort access. Sleeps up to 14 guests, perfect for family vacations and group getaways. Best of all, you're walking distance to The Retreat Clubhouse with lazy river, water slides, resort pools, fitness center, and more.
Luxury Home w/ Pool & 6 Beds near Disney
Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.
Luxury Disney Villa | Theater, Arcade, Heated Pool
✨Welcome to your ultimate luxury Disney getaway! This beautifully designed 5-bedroom, 5.5-bathroom villa offers everything you need for an unforgettable vacation—from a private heated pool and relaxing jacuzzi to a dedicated movie theater with Sonos surround sound, an arcade, multiple Xbox gaming stations, and spacious gathering areas for the whole family. Located just minutes from Walt Disney World in the prestigious Reunion Resort area,✨
Brand new luxury near clubhouse / lake view (405)
STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! Modern Lake View Apartment – Near Disney, Universal , Outlets This beautiful apartment was fully redecorated with all-new furniture by B & Design (By Barbara Costa), featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake.
Luxe Family Retreat | Pool Villa Near Disney & MCO
Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlando’s top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.
Reunion Resort 1st Fl Condo | Near Disney | Patio
Renovated ground-floor condo inside guard-gated Reunion Resort, minutes from Disney and Orlando attractions. Can sleep 4 with king size bed and premium memory foam sofa pull out. Best for couples, small families, and park trips—easy no-stairs access and a private patio. Highlights: modern kitchen, free parking, fast Wi-Fi, and a quiet place to recharge after the parks.
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.
11BR Brand-New Home w/ Themed Rooms&Cinema | 11127
This spacious house in Paradiso Grande features 11 suites and an additional guest restroom, comfortably accommodating up to 28 guests. Designed for both comfort and privacy, it’s the perfect choice for large groups, family gatherings, or special occasions, offering plenty of space for everyone to relax and enjoy.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Gathering paradise with golf view and game room
Paradise Lake Lodge
7851 Luxury 5BR Home w/ Private Pool Near Disney
Large Private Home on Golf course by Disney
Orlando Dream Escape | Private Pool | Disney
4BR Disney & Universal Themed Villa Reunion Resort
Modern 3BR Family Home Near Shops & Disney
Modern Luxury Kissimmee Retreat
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 SGD | $197 SGD | $209 SGD | $215 SGD | $183 SGD | $189 SGD | $185 SGD | $163 SGD | $150 SGD | $157 SGD | $178 SGD | $209 SGD |
| 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.
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- Walt Disney World Resort
- Universal Studios Florida
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Universal Orlando Resort
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Epcot
- Kia Center
- Camping World Stadium
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ESPN Wide World of Sports
- ChampionsGate Golf Club
- ICON Park
- Aquatica
- Southern Dunes Golf and Country Club