Osceola County Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Osceola County, Florida, USA

10.0 (4 Reviews)
2 Bedrooms 8 Guests
|
10.0 (13 Reviews)
9 Bedrooms 21 Guests
|
10.0 (3 Reviews)
1 Bedroom 2 Guests
From US $178 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
From US $166 per night
|
10.0 (3 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 8 Guests
|
10.0 (11 Reviews)
3 Bedrooms 6 Guests
From US $585 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
9.4 (8 Reviews)
1 Bedroom 6 Guests
|
10.0 (10 Reviews)
5 Bedrooms 10 Guests
From US $223 per night
|
10.0 (9 Reviews)
3 Bedrooms 8 Guests
|
10.0 (8 Reviews)
6 Bedrooms 18 Guests
|
10.0 (8 Reviews)
4 Bedrooms 10 Guests
|
10.0 (7 Reviews)
6 Bedrooms 14 Guests
10.0 (71 Reviews)
1 Bedroom 4 Guests
From US $224 per night
|
10.0 (7 Reviews)
5 Bedrooms 10 Guests
From US $242 per night
10.0 (7 Reviews)
4 Bedrooms 14 Guests
|
10.0 (6 Reviews)
4 Bedrooms 9 Guests
9.8 (35 Reviews)
1 Bedroom 4 Guests
|
10.0 (6 Reviews)
4 Bedrooms 10 Guests
|
10.0 (6 Reviews)
4 Bedrooms 10 Guests
10.0 (6 Reviews)
4 Bedrooms 9 Guests
From US $205 per night
|
10.0 (5 Reviews)
7 Bedrooms 20 Guests
New Upstay Champions Gate Home w Private Pool & BBQ
9.2 (7 Reviews)
4 Bedrooms 10 Guests
|
10.0 (5 Reviews)
3 Bedrooms 6 Guests
From US $970 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
New Upstay: Resort-Style 12BR Villa—Bella Vida Resort
9.0 (18 Reviews)
12 Bedrooms 24 Guests
|
10.0 (5 Reviews)
5 Bedrooms 10 Guests
From US $845 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
New Upstay Condo w Pool & Sauna Sleeps 8
9.0 (7 Reviews)
3 Bedrooms 8 Guests
|
10.0 (5 Reviews)
4 Bedrooms 11 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
|
10.0 (5 Reviews)
4 Bedrooms 8 Guests
New Spacious 5-bedroom townhome 13miles from Disney Parks
9.0 (2 Reviews)
5 Bedrooms 12 Guests
|
10.0 (4 Reviews)
4 Bedrooms 8 Guests
From US $282 per night
|
10.0 (4 Reviews)
5 Bedrooms 14 Guests
New Upstay—Vibrant Home w Themed Rooms, Pool & Games
8.6 (17 Reviews)
8 Bedrooms 20 Guests
From US $200 per night
|
10.0 (4 Reviews)
4 Bedrooms 8 Guests
New Upstay: Sonoma Resort Mansion w/Pool & Games Room
8.0 (11 Reviews)
10 Bedrooms 20 Guests
|
10.0 (4 Reviews)
4 Bedrooms 10 Guests
New Upstay - Magic Mansion w Pool-Spa-Cinema-Games
8.0 (7 Reviews)
15 Bedrooms 33 Guests
|
10.0 (4 Reviews)
7 Bedrooms 14 Guests
From US $450 per night
|
10.0 (4 Reviews)
9 Bedrooms 16 Guests
New Park Hopper Paradise At Regal Oaks
8.0 (1 Review)
3 Bedrooms 6 Guests
New Hilltop Villa: Star Wars/Princess room near Disney and Universal
|
10.0 (4 Reviews)
5 Bedrooms 10 Guests

About Osceola County Vacation Rentals

With more than 45342 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Osceola County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Osceola County, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Osceola County. Places to stay near Osceola County are 1735.17 ft² on average, with prices averaging US $395 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Osceola County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Osceola County Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Osceola County?

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 45342 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.