Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Relax & Play :Luxury Villa Near Disney w/ Pool&Spa
Enjoy a stay at our luxurious fully equipped lakefront vacation pool Villa. All the creature comforts you enjoy at home, plus a few extras! • Beautifully maintained, quiet & safe resort-like neighborhood • Screened in Lanai enclosing private pool & hot tub • Extra privacy as this Villa has no neighbors in the back plus tropical hedges surrounding Lanai. • Only 3 miles to Disney and only 18 miles to Universal • Onsite Washer & Dryer • Fiber Gigabit WiFi 940Mbps • Easy Self checkin • Pet Friendly
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.
3BR / 2BR Heated Pool Home 7 Min to Disney |
✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️
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*
Modern Luxury Themed 7 Bed Pool Villa near Disney
There is only one word that truly describes this spacious luxury Villa and that is STUNNING! The Owners of this fabulous 7 Bedroom 5.5 Bath home have lovingly renovated every room in the Villa to provide the perfect modern location for your Floridian vacation. Not only is the property equipped with everything you could possibly need for your vacation, but it is located on the Emerald Island Resort, which has a host of amenities available for your stay.
4BR Jungle Cruise Villa w/Pool & Spa Near Disney
Welcome to your dream getaway just minutes from Disney! Luxury family retreat – Sleeps 8! Private pool, bubbling spa and jungle-themed theater. • 🛏️ 4 Disney-themed bedrooms with en-suite baths • 🏰 Under 5 miles to Disney parks, shops and dining • 🏝️ Adventureland décor • 👨🍳 Gourmet kitchen + washer/dryer & baby gear • 🅿️ Free parking • 📞 24/7 response Book now and let the adventure begin.
Close to Clubhouse Pool TV + Summer Kitchen w/ BBQ
Enjoy the best of Florida living in this luxury and modern townhouse located in the exclusive Windsor Island Resort, just steps away from the Clubhouse. With an open-concept design by architect Elys Micheline, the home offers over 2,271 sq. ft. of comfort, featuring 5 bedrooms, 4 bathrooms, a private pool, and a stylish summer kitchen, perfect for creating unforgettable moments with family and friends.
8005 Elegant Villa Near to Disney Magic
Formosa Valley Resort - 4 Bedrooms in Orlando offers an outdoor pool, free WiFi, and private parking. The vacation home is conveniently located near popular Disney attractions such as Disney's Boardwalk, Hollywood Studios, and Animal Kingdom. Units include a private bathroom. The nearest airport is Orlando International Airport, 22 miles away. Couples rated the location 9.0 for a two-person trip.
BRAND NEW 4 bedroom near Disney and Universal
BRAND NEW house with 4 bedrooms, 4.5 bathrooms, large living room Integrated kitchen, outdoor area overlooking the preservation area. Excellent location, next to Walmart and 17 minutes from Disney parks. Condominium with Clubhouse, magnificent structure with swimming pool, and gym. All the best at your fingertips and that of your family. Space for up to 2 cars parked in front of the house.
Spacious 3BR/2BA Retreat • Near Disney
Welcome! My husband Dande and I created this cozy 3-bedroom, 2-bath condo as a relaxing retreat for families visiting Disney and beyond. Centrally located in Kissimmee, you’re just minutes from Disney World, Universal Studios, SeaWorld, Gatorland, and more! Enjoy comfort, space, and style in a peaceful, family-friendly setting — the perfect home base for your Florida adventure.
Elegant 6-Suites Home in Encore Reunion
Approximately 10 minutes from Disney World parks and close to all other theme parks (daily free shuttles to and from the parks). This stunning 6-bedroom, 6.5-bathroom 5-star home features a private backyard with pool, hot tub, BBQ area, and a gaming room. We have two exclusive themed rooms, an absolute kid’s dream! Games include a Ping-Pong table, foostable, and much more!
1 Bedroom Villa at Grande Vista Resort w/Amenities
Discover your Orlando oasis at Marriott's Grande Vista resort! Perfectly positioned near world-famous theme parks, our property features an on-site golf academy, 9-hole course, exceptional dining, and shopping. After magical park days, unwind in our emerald resort setting in a spacious one bedroom villa. The ideal base for your unforgettable Orlando adventure!
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Lafitte's Landing Lakeview Cottage - Lakefront!
2BR Lakefront Condo Near Disney 325
Five Star Revs, SuprHst, Dis, Lake, Splash Park!
7 Mi to Disney: Kissimmee Poolside Paradise!
6BR Home w/ Priv Pool Near Disney | Gated Resort
4BR Resort Townhome w/ Private Pool Near Disney
NEW LIST - Private Pool/Spa; Golf Course!
OW012 - Quiet Second Floor Oakwater Home
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 | $176 SGD | $186 SGD | $163 SGD | $151 SGD | $158 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- 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
- Give Kids the World Village
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- ChampionsGate Golf Club