Best Vacation Homes in Osceola County
1100 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R2,008/Night
For 7 Nights R14,062
3756.6 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
R8,575/Night
For 7 Nights R60,019
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- View
R10,778/Night
For 7 Nights R75,445
823 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R1,831/Night
For 7 Nights R12,816
Affordable Luxury Home Near Walt Disney World - Sunshine Villa at Glenbrook Resort, Orlando, Florida
1948.27 ft²
8 Guests
4 Bedrooms
4 Bathrooms
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
R2,172/Night
For 7 Nights R15,207
1100 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R1,831/Night
For 7 Nights R12,816
1963 ft²
10 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R3,760/Night
For 7 Nights R26,321
850 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
R1,990/Night
For 7 Nights R13,927
Osceola County Luxury Rentals
3378 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
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3000 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
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2400 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
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12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
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12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
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3100 ft²
17 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
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1800 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
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5201 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
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Osceola County Pet Friendly Vacation Rentals
15 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R12,686/Night
For 7 Nights R88,799
4305.56 ft²
21 Guests
1 Bedroom
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Pet Friendly
R8,892/Night
For 7 Nights R62,242
R10,493/Night
For 7 Nights R73,458
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
R4,989/Night
For 7 Nights R34,927
R3,770/Night
For 7 Nights R26,389
1914 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R4,577/Night
For 7 Nights R32,030
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
R4,110/Night
For 7 Nights R28,763
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
R2,389/Night
For 7 Nights R16,722
Osceola County Large Vacation Homes
1432 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
R4,139/Night
For 7 Nights R28,982
2561.81 ft²
10 Guests
5 Bedrooms
5 Bathrooms
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R4,884/Night
For 7 Nights R34,186
R16,340/Night
For 7 Nights R114,380
8 Guests
2 Bedrooms
2 Bathrooms
Villa
- Fireplace/Heating
- Air Conditioner
- Internet
R5,441/Night
For 7 Nights R38,093
2604.87 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
R4,652/Night
For 7 Nights R32,569
30 Guests
12 Bedrooms
10 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
R35,271/Night
For 7 Nights R246,896
1914 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
R5,209/Night
For 7 Nights R36,459
12600 ft²
26 Guests
10 Bedrooms
12 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R55,050/Night
For 7 Nights R385,358
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
Cumbrian 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.
Frequently Asked Questions About Osceola County?
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
- 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 Osceola County?
There are 21794 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 47738 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
3534 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R7,971/Night
For 7 Nights R55,792
1450 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
R2,987/Night
For 7 Nights R20,899
1800 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R4,189/Night
For 7 Nights R29,319
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,616/Night
For 7 Nights R25,311
2931 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R5,475/Night
For 7 Nights R38,329
1800 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R4,301/Night
For 7 Nights R30,111
2000 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R4,377/Night
For 7 Nights R30,649
1797 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
R2,676/Night
For 7 Nights R18,726
