Best Vacation Homes in Osceola County
House
9.8(6 Reviews)
1 Bedroom
3 Baths
10 Guests
1963 ft²
Private Pool
Fireplace/Heating
Pool
Kitchen
US $223/Night
7 Nights - US $1,563
House
10.0(24 Reviews)
6 Bedrooms
6 Baths
15 Guests
3756.6 ft²
Spa- Fireplace/Heating
- Pool
Parking
US $509/Night
7 Nights - US $3,564
Apartment
9.0(4 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
Balcony/Terrace- Kitchen
US $264/Night
7 Nights - US $1,845
Cottage
9.4(8 Reviews)
1 Bedroom
1 Bath
6 Guests
850 ft²
- Fireplace/Heating
- Pool
Ocean View- Balcony/Terrace
US $113/Night
7 Nights - US $790
House
Affordable Luxury Home Near Walt Disney World - Sunshine Villa at Glenbrook Resort, Orlando, Florida
10.0(13 Reviews)
4 Bedrooms
4 Baths
8 Guests
1948.27 ft²
Oceanfront
Hot Tub- Fireplace/Heating
- Pool
US $129/Night
7 Nights - US $903
Villa
9.2(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1432 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $230/Night
7 Nights - US $1,609
Cabin
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $350/Night
7 Nights - US $2,448
Villa
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $323/Night
7 Nights - US $2,262
Osceola County Luxury Rentals
House
8.8(3 Reviews)
5 Bedrooms
5 Baths
12 Guests
2400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
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House
8.8(11 Reviews)
6 Bedrooms
5 Baths
17 Guests
3100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
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House
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
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House
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
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Resort
8.0(1 Review)
2 Baths
8 Guests
- Hot Tub
- Pool
- Air Conditioner
- Internet
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House
12 Bedrooms
13 Baths
46 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $7,217/Night
7 Nights - US $50,522
House
Eagle Cove - Private Pool, Sports Court, Sauna, Game Room, Theater, Bowling Alley, Gym, Themed Rooms
8.2(14 Reviews)
14 Bedrooms
17 Baths
36 Guests
21397 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $6,613/Night
7 Nights - US $46,288
Villa
10.0(1 Review)
12 Bedrooms
15 Baths
46 Guests
16000 ft²
- Fireplace/Heating
- Pool
Breakfast- Kitchen
US $6,463/Night
7 Nights - US $45,242
Osceola County Pet Friendly Vacation Rentals
New
Villa
9 Bedrooms
5 Baths
20 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $777/Night
7 Nights - US $5,442
House
10.0(9 Reviews)
1 Bedroom
6 Baths
14 Guests
3196.88 ft²
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
US $610/Night
7 Nights - US $4,272
New
Cottage
4 Bedrooms
5 Baths
10 Guests
2048 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $555/Night
7 Nights - US $3,884
Villa
10.0(8 Reviews)
1 Bedroom
5 Baths
21 Guests
4305.56 ft²
- Fireplace/Heating
- Pool
Pet Friendly- Parking
US $528/Night
7 Nights - US $3,696
New
House
1 Bedroom
3 Baths
12 Guests
16652 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $450/Night
7 Nights - US $3,153
New
House
5 Bedrooms
5 Baths
12 Guests
3014 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $367/Night
7 Nights - US $2,570
House
5 Bedrooms
5 Baths
12 Guests
2200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $332/Night
7 Nights - US $2,321
Osceola County Large Vacation Homes
Villa
2 Bedrooms
1 Bath
14 Guests
3200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $286/Night
7 Nights - US $2,004
House
10.0(10 Reviews)
4 Bedrooms
4 Baths
10 Guests
2604.87 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $276/Night
7 Nights - US $1,934
House
9 Bedrooms
6 Baths
24 Guests
4391 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $709/Night
7 Nights - US $4,960
New
Villa
1 Bedroom
3 Baths
8 Guests
2045 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $256/Night
7 Nights - US $1,795
House
10.0(10 Reviews)
6 Bedrooms
4 Baths
14 Guests
3143.06 ft²
- Spa
- Fireplace/Heating
- Pool
- Parking
US $289/Night
7 Nights - US $2,026
House
9.8(122 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $209/Night
7 Nights - US $1,462
New
Villa
8 Bedrooms
11 Baths
20 Guests
8000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,155/Night
7 Nights - US $15,082
New
Villa
10 Bedrooms
8 Baths
26 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $697/Night
7 Nights - US $4,877
Why Choose Rent By Owner for your Osceola County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Osceola County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as understanding the region’s seasonal patterns helps you find the perfect vacation rentals in Osceola County, Florida, USA, that suit your desired weather and activities.
Peak Season Highlights
Winter (December to February)
During the winter months, you'll enjoy mild weather and an influx of visitors seeking escape from colder climates, making this the busiest time for booking vacation rentals here.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Spring Break (March to April)
This is a popular period when families and travelers flock to the region, ensuring high demand for vacation rentals as everyone looks to take advantage of springtime adventures.
Average Temperature Daytime: 78°F - Nighttime: 58°F
Off-Season Highlights
Summer (June to August)
While summer can be busy, early or late in the season offers fewer crowds, with warm temperatures that are perfect for enjoying outdoor activities at your vacation rental.
Average Temperature Daytime: 89°F - Nighttime: 70°F
Fall (September to November)
Autumn provides a quieter experience with pleasant weather, making it an ideal time to book your vacation rental without the peak season prices and crowds.
Average Temperature Daytime: 82°F - Nighttime: 62°F
Weekly Weather Forecast for Osceola County
How to Book Your Osceola County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Osceola County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 a private outdoor swimming pool to relax under the Florida sun.
- Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
- Explore lush gardens and landscaped yards that add charm to your stay.
- Make use of outdoor grilling facilities for flavorful barbecues with family and friends.
- Benefit from access to tennis courts or other recreational sports amenities nearby.
- Relax in shaded lanai areas designed for comfortable outdoor lounging.
- Discover community amenities such as golf courses or walking trails integral to the region’s outdoor living appeal.
Top Attractions Around Osceola County
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities and family-friendly attractions that showcase the best of Osceola County, Florida, offering a memorable experience just moments from your vacation rentals.
Family Activities
- Walt Disney World Resort: Experience the magic of world-famous theme parks, perfect for family fun and creating unforgettable memories in this renowned destination within the area.
- Gatorland Orlando: Discover a thrilling wildlife park where your family can get up close with alligators and crocodiles, offering an educational adventure right here in the region.
- Silver River State Park: Explore the natural beauty of this scenic park with hiking, kayaking, and wildlife viewing opportunities suitable for all ages in this outdoor haven.
- SeaWorld Orlando: Enjoy interactive exhibits, shows, and rides at this marine-themed amusement park, providing family-friendly entertainment in this vibrant local attraction.
Adult Activities
- Visit Disney's Theme Parks: Experience the magic at world-renowned Disney parks nestled within the area, offering unforgettable entertainment and attractions for adults seeking fun and adventure.
- Explore Local Wineries and Breweries: Discover the region's vibrant craft beverage scene by touring local wineries and breweries that showcase unique flavors and brewing techniques.
- Golf at Top Courses: Enjoy a leisurely day on championship golf courses that provide scenic views and challenging play, perfect for golf enthusiasts visiting here.
- Experience Nature at State Parks: Connect with the outdoors by exploring picturesque state parks that offer hiking, birdwatching, and serene landscapes just a short drive from your accommodations.
Other Places to Stay in Osceola County, FL
Kissimmee
Disney's Maingate West
Four Corners
West Kissimmee
Historic Downtown Kissimmee
Reunion
Windsor Hills
Disney's Maingate East
Windsor Palms
Bellavida
Lake Berkley
Buena Ventura Lakes
Osceola County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Adventure Early: To maximize your experience here, book your vacation rentals in advance to secure the best options and rates in this popular destination.
- Explore Local Attractions: Take advantage of nearby parks and cultural sites to fully enjoy what this region uniquely offers without the hassle of long travel times.
- Identify Prime Accommodation Locations: Choose vacation rentals close to major attractions or transportation hubs for convenience and more time to relax during your stay.
- Immerse Yourself in the Local Environment: Engage with community events or try regional cuisine to enrich your visit to this vibrant destination within the area.
Transportation Options
- Osceola County Airport (Polk County Airport): You can conveniently access this regional airport, offering domestic flights that make traveling to the area straightforward.
- Walt Disney World Bus Service: This reliable transportation option connects you directly to many popular attractions and resorts within the region.
- Rental Car Services: Numerous rental car agencies are available locally, providing flexible mobility options to explore the entire area at your own pace.
- Public Transit - LYNX Bus Service: The area's public bus system offers an affordable way to navigate here and reach key destinations around Osceola County.
Local Customs Options
- Southern Hospitality: Visitors often experience the region's warm and welcoming attitude, reflecting its friendly community and relaxed atmosphere.
You can enjoy regional culinary traditions that highlight fresh, local ingredients, showcasing the area's unique flavor profile. - Celebration of Nature: Respect for the natural environment is evident through outdoor customs and community events celebrating the area's diverse ecosystems.
- Community Festivals: Engaging in local festivals provides insight into the area's vibrant culture and deep-rooted traditions that residents cherish.
Osceola County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Osceola County?
There are a lot of options in Osceola County. If you plan on staying in the Osceola County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osceola County:
- 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
- South Facing Pool Hot Tub Themed Rooms Home Theater Swingset Splash Pad BBQ
- Disney theme rooms,Splashpad, Movie Theater, Private Pool
- Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
- Your Dream Villa, 2 Mls to Disney private pool, jacuzzi, theatre & gamesroom
- Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme
2. How many vacation rentals have private pools in Osceola County?
There are 22051 vacation rentals with private pools near Osceola County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Osceola County are best for families?
If you are looking for a family-friendly vacation home in Osceola County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osceola County:
4. How many Rentbyowner vacation rentals are available in Osceola County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 47939 in the Osceola County 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 Osceola County.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so you should review the specific listing for details. Some rentals offer flexible options, while others may have strict terms. It's best to contact the owner directly if you need clarification.
6. How do I find available dates and book my stay in the region?
You can easily check real-time availability and make a reservation through the listing’s booking system. Ensure your preferred dates are open before completing the process, and reach out to the owner if you have any special requests.
7. Are there any additional fees or charges when booking through this platform?
Additional fees such as cleaning, service charges, or taxes are typically outlined on the property’s listing page. Review all fee details carefully before confirming your booking to avoid surprises.
8. What amenities are typically included with vacation rentals in this destination?
Most properties come equipped with essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features such as pools or pet accommodations, check the individual listing details or contact the host directly.
9. What should I know about check-in and check-out procedures for rentals here?
Check-in and check-out times are specified in each listing. Many hosts offer flexible arrangements, but it’s important to confirm these details beforehand to ensure a smooth arrival and departure process.
Osceola County Top Rated Vacation Rentals
House
10.0(378 Reviews)
6 Bedrooms
4 Baths
14 Guests
3534 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $388/Night
7 Nights - US $2,713
Villa
10.0(328 Reviews)
4 Bedrooms
3 Baths
8 Guests
1450 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $217/Night
7 Nights - US $1,520
House
10.0(323 Reviews)
4 Bedrooms
3 Baths
8 Guests
1800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $328/Night
7 Nights - US $2,299
Condo
10.0(316 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $218/Night
7 Nights - US $1,527
Villa
10.0(280 Reviews)
3 Bedrooms
3 Baths
6 Guests
2931 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $313/Night
7 Nights - US $2,191
House
10.0(244 Reviews)
7 Bedrooms
6 Baths
14 Guests
4000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $457/Night
7 Nights - US $3,198
House
10.0(237 Reviews)
7 Bedrooms
6 Baths
16 Guests
4000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $552/Night
7 Nights - US $3,865
House
10.0(235 Reviews)
5 Bedrooms
5 Baths
10 Guests
2966 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $376/Night
7 Nights - US $2,632
