Best Vacation Homes in Kissimmee
- Hot Tub
- Fireplace/Heating
- Pool
- Spa
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Hot Tub
- Fireplace/Heating
- Pool
- Private Pool
- Oceanfront
- Hot Tub
- Hot Tub
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pool
- Ocean View
Kissimmee Luxury Rentals
- Kitchen
- Parking
- Air Conditioner
- Fireplace/Heating
- Pool
- Kitchen
- Private Pool
- Hot Tub
- Fireplace/Heating
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Oceanfront
- Hot Tub
Kissimmee Pet Friendly Vacation Rentals
- Hot Tub
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pool
- Pet Friendly
- Hot Tub
- Spa
- Fireplace/Heating
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Hot Tub
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
Kissimmee Large Vacation Homes
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Air Conditioner
- Internet
- Oceanfront
- Hot Tub
- Spa
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Air Conditioner
- Internet
- Private Pool
- Hot Tub
- Fireplace/Heating
Why Choose Rent By Owner for your Kissimmee Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Kissimmee Vacation Rentals
Where are the best neighborhoods to stay in Kissimmee?
When planning your trip to Kissimmee, Florida, choosing the right neighborhood can greatly enhance your vacation experience. Each area offers a unique atmosphere, whether you're seeking proximity to family-friendly attractions, convenient access to entertainment venues, or peaceful surroundings for relaxation. Exploring neighborhoods within Kissimmee allows you to find the perfect setting that matches your travel preferences, making your stay both comfortable and memorable. With a wide selection of dependable vacation rentals in prime locations, your ideal getaway is just a booking away.
West Kissimmee
This area offers a tranquil retreat with spacious vacation rentals, making it ideal for travelers seeking relaxation near Orlando’s major attractions. The region provides convenient access to theme parks while maintaining a peaceful atmosphere.
View 16785+ Rentals in West KissimmeeBay Lake
Nestled close to the heart of the region, Bay Lake is known for its scenic surroundings and proximity to some of the area's most popular attractions. Guests here enjoy easy access to vibrant entertainment options within a beautiful lakeside setting.
View 930+ Rentals in Bay LakeHistoric Downtown Kissimmee
The historic district exudes charm with its quaint streets and cultural appeal, offering a unique stay experience in the midst of local history. It’s perfect for those who want to explore authentic Florida heritage while enjoying modern conveniences.
View 8109+ Rentals in Historic Downtown KissimmeeWindsor Hills
Known for its family-friendly atmosphere, Windsor Hills features well-equipped vacation homes in a secure community. It’s an excellent choice for convenience and comfort, with easy access to nearby theme parks and family activities.
View 1640+ Rentals in Windsor HillsOrange Lake
Surrounded by lush landscapes, Orange Lake offers a relaxing environment with amenities geared toward outdoor recreation. Its location makes it a prime spot for visitors seeking both adventure and leisure.
View 132+ Rentals in Orange LakeLake Berkley
This neighborhood boasts serene lakeside views and spacious vacation homes, ideal for guests looking for a peaceful escape. The area’s natural beauty complements its close proximity to local attractions.
View 172+ Rentals in Lake BerkleyWindsor Palms
Popular among travelers seeking a resort-style experience, Windsor Palms offers a variety of well-appointed vacation properties with excellent community amenities. It’s a perfect base for exploring the region’s top destinations.
View 877+ Rentals in Windsor PalmsBellavida
Bellavida features a gated community with luxurious vacation rentals set amidst lush landscaping. Visitors appreciate its prime location and the serene environment for a memorable stay.
View 261+ Rentals in BellavidaBest Times to Visit Kissimmee
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as the region offers different attractions and weather patterns depending on the season, making it essential to plan your stay accordingly for a memorable getaway.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences warm weather and lively local events, making it an ideal time to enjoy your vacation rental in this destination.
Winter Holidays (December to February)
The winter months bring cooler temperatures and festive celebrations, providing a charming setting for your stay in this region.
Off-Season Highlights
Summer (June to August)
Summertime in the area features hot temperatures and lighter crowds, offering excellent opportunities for budget-friendly stays at your preferred vacation rentals.
Fall (September to November)
Autumn brings mild weather and fewer visitors, creating a peaceful atmosphere for exploring and relaxing at your vacation rental in this destination.
Weekly Weather Forecast for Kissimmee
How to Book Your Kissimmee Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Kissimmee
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor swimming pools available at many properties, perfect for relaxing after a day of exploring the region.
- Make use of private or shared patios and decks to unwind and soak up the sunny Floridian weather.
- Take advantage of well-maintained outdoor grilling areas for family barbecues in the warm climate.
- Benefit from lush landscaped gardens and scenic courtyards that provide tranquil environments for your stay.
- Participate in outdoor sports facilities such as tennis courts and basketball courts often available on-site.
- Relax in outdoor lounge areas designed for socializing or enjoying the evening air in this popular destination.
- Utilize spacious yards and lawns, ideal for outdoor activities or simply soaking up the sunshine here in the region.
Top Attractions Around Kissimmee
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of activities nearby, from exploring world-class theme parks to engaging in outdoor adventures, making it an ideal destination for your next vacation rental stay.
Family Activities
- Disney's Animal Kingdom Theme Park: You can explore this iconic Disney park to see exotic animals and enjoy immersive rides, making it a favorite family activity here.
- Old Town Kissimmee: Stroll through this lively area with classic car shows, family-friendly shops, and casual dining options, perfect for spending quality time together in the region.
- Kissimmee Lakefront Park: Relax and have fun at this scenic lakeside park featuring playgrounds, picnic areas, and paddle boat rentals, ideal for outdoor family outings.
- Celebration Town Center: Discover this charming community with entertainment, shopping, and food options that cater to families looking for a relaxed day out nearby here.
Adult Activities
- Walt Disney World Resort: Immerse yourself in world-renowned entertainment and attractions at this iconic destination, just a short drive from your Kissimmee vacation rental.
- Old Town Shopping and Entertainment District: Experience lively shopping, dining, and live entertainment that captures the vibrant spirit of the region’s nightlife and local culture.
- Gatorland: Encounter Florida's native wildlife up close with thrilling shows and exhibits that showcase the area's unique natural heritage.
- Shopping at Osceola Square Mall: Indulge in retail therapy and find great deals at this popular shopping center near your vacation rental here in the region.
Other Places to Stay in Kissimmee, FL
Kissimmee Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy a more relaxed experience and better deals on local attractions and accommodations.
- Utilize Local Transportation Options: Taking advantage of public transit or rental cars can help you explore the region conveniently and affordably, maximizing your time here.
- Choose a Strategic Location for Your Stay: Booking nearby popular attractions ensures easier access to the area's highlights and reduces travel time during your trip.
- Explore the Area’s Dining and Entertainment Choices: Sampling local eateries and entertainment venues enhances your visit and provides authentic experiences in this destination.
Transportation Options
- Shuttle Services: Reliable shuttle services are available to and from the area's major attractions, making transportation convenient for travelers staying in local vacation rentals.
- Rental Cars: Renting a car offers you the flexibility to explore the region at your own pace while staying comfortably close to your chosen vacation rental property.
- Public Buses: The local bus system provides an affordable way to navigate the region and reach key destinations near your vacation rental in this popular destination.
- Taxis and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft operate throughout here, providing quick, dependable transportation right to your vacation rental doorstep.
Local Customs Options
- Southern Hospitality: You’ll notice a warm and friendly attitude in the area, reflecting the region's famous southern hospitality that welcomes visitors with open arms.
- Festive Celebrations: Participating in seasonal festivals and events is common here, showcasing the area’s vibrant culture and love for spirited gatherings.
- Respect for Nature: The region emphasizes environmental conservation, so you are encouraged to respect local parks and natural sites during your stay.
Kissimmee Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Kissimmee?
There are a lot of options in Kissimmee. If you plan on staying in the Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kissimmee:
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
- Water View - Pool & Spa - 3.5 miles to Disney - BBQ
- Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
- Amazing villa close to Disney with 5* Reviews
- Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
- Conservation View - Hot Tub - Free Pool Heat - Very Private
- BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
- Our DisneyDreamVilla - minutes to DisneyWorld!
- Family friendly, 10 mins to Disney, WIFI, Resort style amenities, Backyard pool
2. How many vacation rentals have private pools in Kissimmee?
There are 21691 vacation rentals with private pools near Kissimmee. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Kissimmee are best for families?
If you are looking for a family-friendly vacation home in Kissimmee, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Kissimmee:
4. How many Rentbyowner vacation rentals are available in Kissimmee?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 46980 in the Kissimmee area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Kissimmee.
5. What is the cancellation policy for vacation rentals in this area?
6. Are there any age requirements or restrictions when booking a vacation rental here?
7. How do I find vacation rentals that allow pets in this destination?
8. What amenities are typically included in vacation rentals in this part of Florida?
9. How can I confirm the availability of a specific vacation rental during my preferred travel dates?
Kissimmee Top Rated Vacation Rentals
- Private Pool
- Hot Tub
- Fireplace/Heating
- Hot Tub
- Spa
- Fireplace/Heating
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Private Pool
- Hot Tub
- Fireplace/Heating
- Private Pool
- Hot Tub
- Fireplace/Heating
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Pool
- Ocean View
