Compare Vacation Rentals & Rent By Owner Homes in Windward, Placida, Florida, USA
About Windward Vacation Rentals
With more than 1018 Windward 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 Windward.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windward, 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 Windward. Places to stay near Windward are 1035.75 ft² on average, with prices averaging US $312 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Windward with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Windward Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windward?
- Luxury TOWNHOUSE directly ON GULF/OCEAN - Sunset view, Pool, Tennis, Wifi, Pets!
- Gulf Front on a ISLAND, 1 pet, tennis/pickleball , kayaks, SUP POOL is CLOSED
- Gulf Front on an island,kayaks,tennis/pickleball SUP, 1 pet POOL IS CLOSED
- Waterfront Steps to Beach, Huge Deck, 1 pet, Kayaks, SUP, Dock sleeps 8
- Beachfront-Vacation on a Tropical Island! Pool and tennis closed at this time
- Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
- Palm Island /Don Pedro Island beach house with POOL! [Pet-Friendly]
- Honeymoon or Anniversary getaway beachfront with bay dock!
- Waterfront, Gulf Views,kayaks,SUP ,1 pet. Pool & tennis are closed at this time
- "She Sells Seashells" GULF VIEW Free Ferry ,Parking, Heated Pool, Boat Slip
How many Rentbyowner vacation rentals are available in Windward?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1018 in the Windward 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 Windward.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Vacation Rentals in Florida | 52 |
