Holiday rentals in Kissimmee
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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
Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
Affordable Disney Family Townhome Pool/BBQ/Gym
Welcome to your modern 3-bedroom, 2.5-bath townhouse in a resort community just minutes from Disney. Enjoy a spacious open-plan living area, fully equipped kitchen and private screened patio. Resort-style amenities include pools, clubhouse and fitness center. In a quiet, secure neighborhood, this home offers easy access to Orlando’s world-famous theme parks, shopping centers and restaurants. Perfect for families or groups looking to experience the magic of Florida with all the comforts of home.
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.
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.
Orlando Dream Escape | Private Pool | Disney
Enjoy this beautiful renovated house with a private pool in Kissimmee. Ideal for families and groups of up to 8 guests. It has 3 bedrooms, 2 bathrooms, a sofa bed, a fully equipped kitchen, Wi-Fi, a washing machine, a dryer and free parking. Located near Disney, Universal, SeaWorld, restaurants and shops. Relax, enjoy the sun, and create unforgettable memories with family and friends. Just minutes from Orlando's top attractions ✅ Private pool
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.
7851 Luxury 5BR Home w/ Private Pool Near Disney
Create unforgettable memories in this modern 5-bedroom, 5-bathroom home in Reunion Village, near Disney. Enjoy a private screened-in pool, game room, second-floor loft, open-concept living and dining area, modern kitchen, multiple king-sized bedrooms, themed bedrooms, high-speed Wi-Fi, TVs, washer/dryer, free parking, self check-in, and access to eligible Encore Club amenities. Ideal for families and groups.
405 Storey Lake brand new clubhouse and lake view
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.
Exquisite Luxury Home Minutes from All Theme Parks
Luxurious Mid Century Modern decorated and newly renovated stylish home at the heart of Orlando in the famous Dr. Phillips area, just minutes away from all Orlando major theme parks, the famous restaurant row with variety of major chain/award wining restaurants and specialty grocery stores. Perfect for family or group up to 8 people to enjoy a comfortable stay. Enjoy!
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.
7 BD/ 7 BA/ Solara Resort (2327 SR)
• Community: Solara Resort • 7 Bedrooms/ 6.5 Bathrooms/ Sleeps 14 • Disney World® (7.5 miles) SeaWorld (17.0 miles) • Convention Center (18.0 miles) ICON Park ( 19.7 miles) • Universal Studios (20.8 miles) Epic Universe (20.3 miles) • Location: Sea Rock Rose Trl, Kissimmee, FL 34747
2026 New Themed 06 Bedrooms at Solara Resort
* Accommodates: * Bathrooms: 4,5 * Bedrooms: 6 * Property type: Luxury Villa * Location: Solara Resort
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Modern 3BR Family Home Near Shops & Disney
Magic House- Pool - Near Disney 14+
Gorgeous 5BR at Encore Resort next to Disney - 305
Lakeview Villa w Spider~Star Wars Themed, Games!
Bright & Modern Stay Closest to Disney
Santosh Cove Retreat
Lake Front House, Themed Br, Game Room, 16 Guests
Spacious townhome near Disney w/ patio
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £111 | £116 | £123 | £110 | £97 | £103 | £109 | £96 | £88 | £93 | £105 | £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.
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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
- Magic Kingdom Park
- Camping World Stadium
- Universal's Volcano Bay
- Epcot
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- University of Central Florida
- Discovery Cove
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Tinker Field
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club