Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Comfort Home with BBQ, Private Pool & Hot tub
Step into our inviting single home where coziness eagerly awaits you! This beautiful Villa is nestled in the prestigious, award-winning Terra Verde Resort, a guard-gated community in Kissimmee, just 30 feet from the clubhouse and a mere 10 minutes from Disney. BBQ grill & Pool Heating are optional and must be requested at least one day before arrival. Terra Verde Resort HOA requirement: Upon check-in, guests must purchase a $25 non-refundable gate card for each vehicle entering the community.
Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!
Family Resort/Waterslides/Close 2 Disney
Discover simple comfort in this 2-bdrm, 2.5-bath townhome nestled in the highly sought-after gated Regal Oaks community, just minutes from the enchanting world of Disney. The spacious open-concept living room overlooks a contemporary dining area and fully equipped kitchen, complete with sleek countertops & stainless steel appliances. Upstairs, you'll find 2 generously sized bedrooms, each with its own ensuite bath. The real gem of this villa is the private lanai, where you can unwind in the hot
Lush 5BR Home w/ Pool, Game & Themed Rooms
Welcome to your ultimate retreat in the heart of Storey Lake, boasting: - Cozy 5BR home combines luxury with the enchantment of Disney, offering an unforgettable escape. - Immerse yourself in the Star Wars and Mickey-themed bedrooms, or relax by your private pool. - Unwind with entertainment on smart TVs & high speed Wi-fi for connectivity. - Free parking is available for convenience. - Prime location near Universal Studios guarantees an unparalleled experience, promising cherished memories.
Gorgeous 5BR @ Encore Next to Disney - 305
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 beautiful backyard, 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 *PLEASE MAKE SURE TO READ THE HOUSE RULES*
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.
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!
❤️THE❤️ ADVENTURE❤️ HOUSE❤️ (3BD/2BA/4 SmartTV/Lakefront)
⚠️ BOOKING REQUIREMENTS: (please do not book if you dont meet or do not agree with the requirements) ✔️Minimum age of 25 yo is required to book this unit and be ready to present photo ID when requested. Must attend the trip. ✔️Be one single family living outside Orlando area and visiting parks. ✔️Be kind, clean, and well-organized. ✔️Must carefully read and agree with (1) listing description, (2) house rules and (3) checkout instructions.
Beautiful 2BR Condo with Great Views on Resort
Whether you’re visiting the parks or looking to unwind, this stunning modern condo offers the best of both worlds. Just minutes from Disney and perfectly located between Universal and all of Orlando’s top spots. Enjoy lake and resort views from your private balcony, fast Wi-Fi, and amazing amenities: pools for all ages, water fun, gym, jacuzzi, tiki bar, boating, sports courts, and more. No resort fees and walking distance to everything!
Retreat w/ Themed Room + Resort | 10 min Disney
Welcome to your dream vacation home! Ideally located at The Hub at Westside Reserve, this stunning 3-bedroom, 3-bath townhome offers comfort, privacy, and style for up to 8 guests. Enjoy a themed bedroom kids will love and a dedicated workspace for adults. With easy access to I-4 and Highway 429, you’re just 10 minutes from Disney and close to top restaurants, shops, and attractions. Perfect for families seeking luxury and relaxation!
5BR Pool Villa Near Disney
Stay in our beautiful villa at the brand-new Windsor Cay Resort, perfect for families and groups seeking comfort, safety, and fun in Orlando. The home sleeps up to 12 guests and features 5 bedrooms — including two themed rooms — a private heated pool*, fully equipped kitchen, laundry room, and fast Wi-Fi. Located just 20 minutes from Disney, with easy access to Universal, SeaWorld, and outlet shopping.
Upscale Townhome @ Windsor Hills
This NEWLY renovated and beautifully decorated home-away-from-home is perfectly located 5 miles from Walt Disney World® Resort. Relax in your private heated plunge pool and make yourself at home in this upscale townhouse. With hardwood floors throughout the entire townhouse and a modern flare, this 3-bedroom, 3-bathroom home that sleeps up to a family of 8 will feel like an oasis.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Beautiful Decor 2BR Apartment Near Disney
Ultimate Disney Vacation Home w/ Game Room + Pool
Special Offer Storey Lake 2Bedr 2Bath MN305
Villa 2655, Heated Pool/Grill, Game Rm, & PS5
Windsor Hills 4BR Villa | Private Pool + Game Room
Paradise Palms Resort 4 Bedroom Pool Townhome
Magical Stays Near Disney
Lavish 5 BR Villa, Movie Room, Resort - by Blue Sk
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 | $187 SGD | $164 SGD | $151 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
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- 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
- Reunion Resort Golf Courses - Palmer & Watson