Compare Vacation Rentals & Rent By Owner Homes in Oakland, Winter Garden, Florida, USA
About Oakland Vacation Rentals
With more than 74 Oakland 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 Oakland.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Oakland, 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 Oakland. Places to stay near Oakland are 446.36 ft² on average, with prices averaging US $193 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Oakland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Oakland?
What are the top vacation rentals in Oakland?
- Walkable Winter Garden Bungalow: 3 Blocks to Dtwn
- WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
- Spacious garage apartment in Winter Garden that sleeps four.
- Dtwn Winter Garden Home: 12 Mi to Disney!
- Mid Century Hipster
- 16 Mi to Disney: Cottage w/Deck in Winter Garden
- Walkable Winter Garden Bungalow 3 Blocks to Dtwn
- Modern Florida Bungalow: 3 Miles to Winter Garden!
- Quaint 1Br/Ba entire guest house in heart of Hist. Downtown Winter Garden
- Enchanted 2 Bedroom Home near Downtown Winter Garden
How many Rentbyowner vacation rentals are available in Oakland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 74 in the Oakland 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 Oakland.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Killarney Vacation Rentals in Orlando, Florida | 26 |
