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
8070-304 Luxury 2BR Apt Kissimmee Orlando Disney
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped Apartment Condo Hotel for up to 6 guests, located right behind Sunset Walk, MargaritaVille Resort & Island H2O Water Park in Kissimmee. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. Everything you need is steps away: Restaurants, Ice Cream, Shops, Studio Movie Theater, Water Park, Live Music, Slingshot, Supermarkets & more... EV Charger Available.
Exquisite First-Floor Condo, 7 Min. to Disney
Step into our charming condo, where coziness awaits you! Our incredible property has everything you need to make your holiday even more magical. Situated in the heart of Orlando, this property is close to various attractions. Our guests have access to a private balcony and exceptional amenities. The community has a fully equipped gym, lazy river, pool, volleyball courts, epic water slides, kayak & mini-golf that make you feel like you were staying in a luxury resort.
NEW*Avatar/Inside Out• Pool & StoreyLake Resort
✨ Your Orlando Fun Spot – 6 Miles to Disney! ✨ Freshly remodeled 4BR with 2 king suites, Avatar & Inside Out rooms, and 3 baths. Private screened pool with outdoor TV & dining. Enjoy Storey Lake’s water park, lazy river, tiki bar & mini golf. Family-ready with high chair, stroller & Pack ’n Play, plus pet-friendly! 📍 Perfect location: 🏰 Disney – 7 miles 🐬 SeaWorld – 11 miles 🎢 Universal – 17 miles ✈️ MCO – 20 miles 🌟 Your vacation starts here—book today!
Modern 4bdr Storey Lake w/themed rooms near disney
Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.
Amazing Retreat at Lake Berkley
5-Bed Lake Berkley Villa with Private Pool - Near Disney! Stunning 5-bed, 3-bath home in gated Lake Berkley Resort, minutes from Disney. Sleeps 10 with king master, 1 king, 1 queen, 2 twins. Enjoy a private pool, game room, full kitchen, Wi-Fi, TVs, and laundry. Resort offers clubhouse, tennis, and lake views. Perfect for families, just 10 min from theme parks, dining, and shopping. No smoking/pets. Pool heat extra. Book your magical Orlando escape!
Waterfront Wizarding Near Universal's Harry Potter
This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.
The Disney House • Immersive Rooms • Gaming Lounge
Welcome to our magical 3-bedroom getaway, newly decorated and thoughtfully designed to create an immersive Disney experience for the whole family! Step into beautifully themed bedrooms featuring Toy Story, Star Wars, & Beauty and the Beast, making every stay unforgettable. Also enjoy a Mario arcade room and Mickey decorations at the home. Perfect for families and Disney lovers! The Grill has an additional cost to rent for the reservation of $75.
Comfy King Bed Apt w/Pool & Gym and Close to Parks
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
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.
Boho Luxe Retreat • Near Disney Parks
Welcome to Boho Luxe retreat ✨ a beautifully designed house created for comfort, rest, and unforgettable moments. This spacious home blends modern elegance with a cozy boho touch, perfect for families and groups. Enjoy stylish bedrooms, inviting living spaces, and a relaxing atmosphere after a day at the parks. Conveniently located near Disney, dining, and attractions, this home is your ideal Florida getaway. ☀️🎢
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Casita Coco | Private Pool | Foosball | BBQ
Resort-Style Home Near Disney | Pool | Game Room
Decadent Penguin - Storey Lake by Shine Villas
Modern & Bright • Near Disney & Outlets
Wheelchair Accessible Home | ADA Bath + Pool Lift
Brand New Luxury 4BDRM home near Disney
Disney Vacation Home 4 Bedroom 3.5 Bath
Luxury Disney Escape with themed Rooms
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $180 SGD | $185 SGD | $193 SGD | $188 SGD | $166 SGD | $177 SGD | $187 SGD | $164 SGD | $151 SGD | $159 SGD | $179 SGD | $211 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
- 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