Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Casa Bella Mediterranean Style near Disney
Welcome to this beautifully 4-bedroom, 3-bath pool home located in the desirable Westside Tuscany community — a peaceful Mediterranean-style enclave just minutes from Walt Disney World and Orlando’s world-class attractions. Step inside to a bright and spacious open living area with large windows and sliding doors that lead directly to your private screened pool, where you can relax and enjoy peaceful wooded views after a fun day at the parks. Enjoy your own private Florida retreat! Book now!
Lakeview Themed Home w/ Pool & Theater Near Disney
Welcome to this stunning 7-bedroom single-family getaway at Storey Lake Resort! This unit offers a cozy and modern decoration, themed bedrooms, a top-notch game room, private pool with a breath-taking lake-view, and more. A perfect family getaway for up to 20 guests inside a wonderful community. • Resort: Storey Lake • 7 Bedrooms/ 6 Bathrooms/ Sleeps 20 • Disney (5 miles) • Sea World (7 miles) • Convention Center (9 miles) • Universal (10 miles) • Location: Parenthesis Ave, Kissimmee, FL 34746
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.
*Modern Luxury Reunion Oasis | Pool, Spa & Cinema
Wow-factor luxury meets unforgettable family fun, just minutes to Disney, at this show-stopping home in the exclusive Reunion Resort. Step outside to a massive 2,400-sq-ft southwest-facing pool deck with outdoor kitchen, private pool, overflow spa, and no rear neighbors—perfect for all-day sun and sunset swims. Inside: private movie theater, billiards game room, and spectacular Star Wars & Frozen II theme bedrooms with tube slide, plus Xbox and PlayStation for nonstop entertainment.
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.
Pet-Friendly Pool Home Near Orlando
Welcome to your perfect Orlando retreat! This beautiful and spacious home offers a blend of modern comfort, stylish design, and exceptional amenities — all just minutes from the top parks and attractions. Enjoy a private screened-in pool, elegant interiors, and thoughtfully designed spaces ideal for families, groups, or long stays. Every detail has been curated to provide comfort, relaxation, and an unforgettable vacation experience.
Storey Lake brand new near Disney lake & club view
STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! This beautiful apartment was fully redecorated with all-new furniture by B & Design, featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake. Located in a luxury resort just minutes from Disney parks, Universal Studios, outlets, Walmart, Publix, and the airport.
Elegant 5B & 3B Private Pool Villa near Disney
Luxury pool home in Formosa Gardens just minutes from Disney. Enjoy high ceilings, open living spaces, and a private screened pool and lanai, perfect for relaxing after the parks. Spacious and comfortable for families or groups, featuring a large dining area, fast WiFi, and everything needed for a smooth stay. Located in a quiet, safe community close to restaurants, shopping, and major attractions.
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!
Disney/Orlando Animal Kingdom Luxy Stay
Our Animal Kingdom themed house is located only short 15 amay from Disney Parks. Includes 4 themed bedrooms, heated pool, fully stuffed kitchen and relaxing spa for mom. Arcade, board games form entire family, and Poker table for older kids.
Luxurious Dream 4/3 Bedroom Home w/private Pool
Located a short 15 minute drive to Disney, this luxury design inspired 4 bedroom, 3.5 bath is perfect for a family, multi family or romantic weekend away with your favourite person.
2026 Brand New 6BR w/ Theater & Game Room/Solara
*The Space * Bathrooms: 5 * Bedrooms: 6 * Sleep 13 * Property type: Luxury Villa * Location: Solara Resort
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Luxury 7BR Villa, Pool, Spa & Game Room
Best Location! Best Location!Villa in Kissimmee
Luxury 8BD Theater Game Pool Golf Firepit - Disney
Private Pool + Spa | Game Room | Near Disney
6br Lake Front, Themed & Game Room w/ Private Pool
Solara9120 Drift| 6BR Villa w/ Pool & Luxury Spa
NEW Reunion Resort Disney Home|5BD|Pool|Bbq|Movie
9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa
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 | £108 | £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 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
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- University of Central Florida
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club