Compare Vacation Rentals & Rent By Owner Homes in Winter Park, Florida, USA
About Winter Park Vacation Rentals
With more than 183 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 808.76 ft² on average, with prices averaging US $227 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
Winter Park Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Winter Park?
- A curated stay in the Historic College Quarter
- Great Family Home
- GREAT LOCATION 🏡
- Amazing lakefront mid-modern 3-bed Winter Park home surrounded by Natural Beauty
- Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!
- Home away from home in the heart of charming Winter Park!
- LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
- Cozy Comfort Just 2 Blocks From Park Ave!
- 6 Mi to Downtown Orlando: Quiet Home w/Sunroom
How many Rentbyowner vacation rentals are available in Winter Park?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 183 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 | 557 |
| College Park Vacation Rentals in Orlando, Florida | 44 |
| Goldenrod Vacation Rentals in Orlando, Florida | 171 |
| Baldwin Park Vacation Rentals in Orlando, Florida | 544 |
| North Orange Vacation Rentals in Orlando, Florida | 863 |
| Orwin Manor Vacation Rentals in Orlando, Florida | 842 |
