Holiday rentals in Kissimmee
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Quick stats about holiday rentals in Kissimmee
Total holiday rentals
Explore 7,040 holiday rentals in Kissimmee
Nightly prices starting at
Kissimmee holiday rentals start at $13 SGD per night before taxes and fees
Verified guest reviews
Over 277,640 verified reviews to help you choose
Family-friendly holiday rentals
5,830 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 1,120 rentals that welcome pets
Holiday rentals with a pool
6,330 properties feature pools
Rentals with dedicated workspaces
3,970 properties have a dedicated workspace
Wifi availability
6,950 of Kissimmee holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Lake access across Kissimmee rentals
4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Kissimmee
Guests agree: these stays are highly rated for location, cleanliness and more.
Epic stay at Vista Cay!
This 2-bedroom, 2-bathroom apartment at Vista Cay Resort, Orlando, offers an exceptional location for enjoying the best of the city. Just minutes from Orlando International Airport and Walt Disney World, it provides unparalleled convenience for both travelers and residents. Additionally, its proximity to the Convention Center, Universal Studios, SeaWorld, and International Drive grants easy access to major attractions, dining, and shopping, offering a complete experience in the heart of Orlando.
Luxury Retreat at Reunion Resort
Luxury Retreat at Reunion Resort – 12 Miles from Disney! Welcome to our stunning vacation home nestled in the prestigious Reunion Resort! This elegant getaway offers the perfect blend of luxury, comfort, and convenience, making it an ideal retreat for families and groups. The home offers a beautiful back yard pool and spa area for you to enjoy, while playing music through the surround sound system in the house and in the back yard. EV Friendly. With 6 Bedrooms You wont regret staying here.
Haunted Mansion-inspired Ghoulish Sanctuary
Welcome, Foolish Mortals... To the Ghoulish Sanctuary: An immersive Haunted Mansion-themed stay just 15 minutes from Walt Disney World, where candlelights flicker, and the air is deathly still... Experience a one-of-a-kind Haunted Mansion-themed stay for up to 6 people. This spooky rental in Kissimmee lets you inhabit your favorite ghostly estate... if you dare. Ready to play your next campaign and need a place to gather for your DnD weekend? The sanctuary and its spirits await.
Orlando Dream Escape | Private Pool | Disney
Welcome to your perfect Orlando getaway! Enjoy this beautifully renovated home with a private pool, just 20 minutes from Disney, Universal, and SeaWorld. Perfect for families and groups of up to 8 guests. Features 3 bedrooms, 2 full bathrooms, a fully equipped kitchen, fast Wi-Fi, washer & dryer, free parking, and self check-in. Relax, unwind, and create unforgettable memories close to Orlando’s best attractions, shopping, and restaurants. 🏊♀️ Private Pool
*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5
Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.
15BR w/ Game Room, Themed Rooms & Pool
Luxury Disney Villa | 15 Bedrooms, Star Wars Theater, Pool & Spa | Sleeps 32 Experience your private Orlando resort just 15 minutes from Disney. This stunning 15-bedroom villa features themed rooms, a Star Wars movie theater, game room, chef’s kitchen with dual fridges, and a private pool & hot tub. Each bedroom has its own ensuite bathroom and smart TV, perfect for large family vacations and reunions.
Brand new luxury near clubhouse / lake view (405)
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.
Luxe Family Retreat | Pool Villa Near Disney & MCO
Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlando’s top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.
No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!
**We offer a FREE EV Charger! We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.
Cozy family home w/ heated pool 15 min. to Disney
Modern family home in a gated community (very quiet neighborhood). 2391 sq ft with 5 bedrooms, 4.5 bathrooms, heated pool*, BBQ*, gaming room, 60'' Full HD TV, free unlimited high-speed wi-fi, central AC/Heating. 15 minutes driving to Disney.
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.
Kissimmee, Heated Pool, Game Room. Luxury
Amazing and new house in Kissimmee , Orlando 4 Bedrooms, 3 Bathrooms, Heated pool, Jacuzzi, BBQ, Laundry, Mini golf, Game room, Pool table, Futbool net, Hammocks.
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
6BR house sleeps 16 with private pool
Montego Bay Retreat | 15 Min to Disney
4BR Disney & Universal Themed Villa Reunion Resort
Spacious Resort Home for Large Groups near Disney
Luxury Home w/ Pool & 6 Beds near Disney
Large Private Home on Golf course by Disney
Magic Village Resort Gated Community Disney World
Luxury Disney 9BR Villa w/ Theater, Pool & Arcade
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 SGD | $197 SGD | $210 SGD | $215 SGD | $183 SGD | $189 SGD | $186 SGD | $163 SGD | $150 SGD | $158 SGD | $178 SGD | $210 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.
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- Walt Disney World Resort
- Universal Studios Florida
- Disney Springs
- Universal Orlando Resort
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Epcot
- Kia Center
- Camping World Stadium
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure