Compare Vacation Rentals & Rent By Owner Homes in Windermere, Florida, USA
About Windermere Vacation Rentals
With more than 51 Windermere 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 Windermere.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windermere, 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 Windermere. Places to stay near Windermere are 929.21 ft² on average, with prices averaging US $417 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Windermere 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 Windermere, FL
Frequently Asked Questions About Windermere?
What are the top vacation rentals in Windermere?
- The Home of Sweet Peace
- Orlando 20 Guest Villa Centrally Located with Game Room
- 6 MI to Beach! Private Pool, Fire Pit & Game Room
- Beautiful 4 Bedroom Home
- Remarkable House finding at 7.9m distance from Disney and 7.2m to OCCC
- Luxury Retreat in Windermere The Perfect Base for Exploring Orlando
- Arnold Palmer's Bay Hill Club & Lodge
- 3860 - Wonderful and Modern House with pool Close Disney
- Arnold Palmer's Bay Hill Club & Lodge
- Welcome to the Farm House! Excellent Location, Pet Friendly!
How many Rentbyowner vacation rentals are available in Windermere?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 51 in the Windermere 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 Windermere.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Bay Lake Vacation Rentals in Orlando, Florida | 1116 |
| Southwest Orlando Vacation Rentals in Orlando, Florida | 1084 |
| Metro West Vacation Rentals in Orlando, Florida | 363 |
