Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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355 Luxury House | Patio | GameRoom | Pool | Grill
Relax with the whole family at this Stylish Magazine Style house in Davenport, just miles from Disney World Orlando Florida Theme Parks, Universal Studios, Sea World and Legoland. Enjoy our PRIVATE POOL and optional WATER HEATER & GRILL. 4 bedrooms, 2.5 bathrooms, fully equipped kitchen, Smart TV's and strong Wi-Fi all around the house. Themed Games Room in the Garage with Smart TV, Full Size Pool Table & Air Hockey. Close to Posner Village Outdoor Mall, Restaurants & Retail stores.
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!
Luxury Disney Vacation Home on Reunion Golf Resort
This 5 bedroom Luxury family vacation home has one of the most picturesque views in all of Reunion, located on the 14th fairway of the Jack Nicklaus course. 2 MASTER SUITES which over looks your private POOL & SPA. All rooms are professionally decorated with a Disney and a Harry Potter room. Your family will stay busy with the arcade, ping pong table and a large number of board games for all ages. Pool area has a basketball net, New WEBER BBQ and Kamado Joe
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.
COZY Villa w/ Private Pool & Game Room | Kissimmee
Welcome to this cozy and modern townhome located in Kissimmee, near Disney. The perfect choice for those looking for peace of mind, offering themed rooms, private pool, game room, and modern decoration. • Community: Le Reve • 4 Bedrooms/ 3.5 Bathrooms/ Sleeps 10 • Disney (7.1 mi) SeaWorld (10.7 mi) Legoland (32.8 mi) • Convention Center (10.1 mi) Universal Studios (14.1 mi) • Location: Le Reve Court, Kissimmee, FL 34746
Retreat w/ Pvt Pool + Club Access | Disney 15min
Experience comfort, style, and resort living in this beautiful 5-bedroom, 5.5-bathroom vacation home just 15 minutes from Disney. Enjoy elegant living spaces, Smart TVs throughout the home, an Xbox One, and a private screened pool area with patio furniture and a BBQ grill — perfect for relaxing after a fun day in Orlando. The open-concept kitchen and spacious dining area are ideal for gathering with family and friends.
Storey Lake brand new clubhouse and lake view
STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! Modern Lake View Apartment – Near Disney, Universal , Outlets This beautiful apartment was fully redecorated with all-new furniture by B & Design (By Barbara Costa), featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake.
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!
2602SN - Stunning Home 5 Ensuites Near Disney
Sonoma Resort is in the perfect spot, right next to "The Loop," a top-notch shopping and entertainment hub. Plus, you're just minutes away from all the fun at Disney World, Universal Studios, SeaWorld, and some of the best outlets, malls, and golf courses around.
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.
5 Bd/ 5.5 Ba Sleeps 12! Windsor Cay (15839 CC)
• Community: Windsor Cay • 5 Bedrooms/ 5.5 Bathrooms/ Sleeps 12 • Disney (8.2 miles) SeaWorld (18.5 miles) Legoland (31.0 miles) • Convention Center (19.5 miles) Universal Studios (22.3 miles) • Location: Cape Coral Loop, Clermont FL 34714
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
House located 10 minutes from the parks.
Luxury 7BR Orlando Villa | Pool, Spa & Game Room
Rare Gem-20 Minutes from Disney
9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa
Modern 5BR Home with Game Room and Pool at Windsor
Florida HappyNest Secluded Luxury Guesthouse
Modern Villa with Private Pool in Encore
New Modern Townhome | Private Pool | Near Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $191 SGD | $198 SGD | $211 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 7,260 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 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, Pet-friendly and Laptop-friendly workspace 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
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club