Compare Vacation Rentals & Rent By Owner Homes in Winter Park, Florida, USA
About Winter Park Vacation Rentals
With more than 1463 Winter Park 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 Winter Park.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Winter Park, 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 Winter Park. Places to stay near Winter Park are 643.93 ft² on average, with prices averaging US $259 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Winter Park with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Winter Park, FL
Frequently Asked Questions About Winter Park?
What are the top vacation rentals in Winter Park?
- Family & Pet Friendly (*additional pet fee applies), Charming Orlando Home!
- Family Friendly home with Fenced in Backyard to enjoy with kids & pets
- Temporary living that feels like home where you can relax and be yourself.
- Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
- Ideal Location, Charming 4 bedroom home w Pool, fenced yard.
- Stylish Boutique Guest house in Winter Park
- SPRING LAKE GETAWAY SUITE (Detached Guest House)
- Large, beautiful, very comfortable one bedroom on small lake
- Mills Cottage by the Little Lake
- Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
How many Rentbyowner vacation rentals are available in Winter Park?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1463 in the Winter Park 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 Winter Park.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Northeast Orlando Vacation Rentals in Orlando, Florida | 243 |
| College Park Vacation Rentals in Orlando, Florida | 315 |
| North Orange Vacation Rentals in Orlando, Florida | 796 |
| Baldwin Park Vacation Rentals in Orlando, Florida | 151 |
| Orwin Manor Vacation Rentals in Orlando, Florida | 775 |
| Goldenrod Vacation Rentals in Orlando, Florida | 127 |
