Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Margaritaville Cottage,Hot Tub,Arcade, near Disney
Kick back and relax in this cozy two-bedroom cottage inside the gated Margaritaville Resort, only 4 miles from Disney. While the kids have a blast playing over 1,000 games on the full-size arcade machine inside, you can chill out on the patio with a cold drink. Forget crowded resort pools- you’ve got your own private hot tub to unwind in after a long day at the parks. Sunset Walk and the new Island H2O water park are just a short walk away. And bring your furry friend too — we’re pet friendly!
207 Storey Lake Brand new 7 Guests 2 BDR Lake view
STOREY LAKE - 7 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE VIEW ✨ Modern Lake View Apartment – Near Disney & Universal ✨ This beautiful apartment was fully redecorated with all-new furniture by B & Design, featuring a modern, clean, and airy design. luxury resort just minutes from Disney parks, Universal Studios, outlets, Walmart, Publix, and the airport, this community offers top-class amenities for adults and children. ✔ Modern décor ✔ Lake view balcony ✔ Close to attractions & shopping
Gorgeous 5BR at Encore Resort next to Disney 7710
Brand New Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a movie room, a beautiful backyard with a summer kitchen, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions
Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!
Family Vacay with Pool near WDW!
We hope to welcome you to this enchanting family retreat in Kissimmee, Florida, just 20 minutes from the magic of Walt Disney World Resort! This sunlit oasis is designed for unforgettable family vacations. Dive into your screened private pool, a cool oasis under the warm Florida sun, to create memories that'll last a lifetime. After an exhilarating day at the parks, return to this cozy home where you'll find the perfect blend of entertainment and relaxation.
Stay Near Disney w King Bed Amenities PetFriendly
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
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?
The Villa Stay
Welcome to a stunning retreat perfectly located near Orlando’s top attractions, world-famous theme parks, delicious restaurants, and premier shopping destinations are all just moments away. After an exciting day exploring the city, come home to a space designed for relaxation and style. Unwind in modern comfort, enjoy peaceful surroundings, and make unforgettable memories in this elegant villa.
3240 Stylish Townhouse 3BD Comfort and Convenience
Welcome to your home away from home at The Hub at Westside, located in the vibrant community of Kissimmee, near Winter Garden. Our stylish and modern 3-bedroom, 3-bathroom townhouse is designed with your comfort and convenience in mind, perfect for families, business travelers, or vacationers seeking a serene and functional space.
3 Bd/ 3 Ba Sleeps 8! Reunion Resort (7602-201)
• Resort: Reunion • 3 Bedrooms/ 3 Bathrooms/ Sleeps 8 • Disney (5.9 miles) SeaWorld (15.5 miles) Legoland (25.8 miles) • Convention Center (16.6 miles) Universal Studios (19.3 miles) • Location: Cabana Court, Kissimmee FL 34747
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.
Brand NEW 06 Bedrooms with Pool At Solara Resort
The Space • Accommodates: 14 • Bedrooms: 6 • Bathrooms: 5 • Property type: Luxury Villa • Location: Solara Resort
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
5-Star stay near Theme Parks!
2BR Lakefront Condo Near Disney 325
Modern & Bright • Near Disney & Outlets
EP1015SEL - 4 bedrooms pool home on a lake
Brand New 10BR Villa w/ Themed Rooms Near Disney
5BR Luxury Villa • Games & Golf • Near Disney
Aruba Palms Villa Near Disney & Attractions
Stunning 2Bd Apt Near Disney @Storey Lake 304 3191
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 SGD | $186 SGD | $194 SGD | $189 SGD | $167 SGD | $177 SGD | $188 SGD | $165 SGD | $152 SGD | $159 SGD | $180 SGD | $212 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.
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 $26 SGD 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 & child-friendly amenities
Pet-friendly holiday rentals
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
Wifi availability
7,280 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
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Give Kids the World Village
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club