Compare Cottages, Resorts, & Rentals in Windward, Placida, Florida, USA
About Windward Vacation Rentals
There are over 1134 amazing vacation rentals available in Windward. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Windward.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Windward, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Windward. The average size of places to stay near Windward is approximately 1043.13 ft², with prices averaging US $346 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Windward. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Frequently Asked Questions About Windward?
What are the top cottages, summer homes, and lake houses in Windward?
- 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
- Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
- Honeymoon, Anniversary, Kayak, beach retreat; comes with bay dock, kayaks & more
- Waterfront, Gulf view ,1 pet, tennis/pickleball Pool is closed at this time
- "She Sells Seashells" GULF VIEW Free Ferry ,Parking, Heated Pool, Boat Slip
- A Little Slice of Paradise
- 'Incommunicado ' ~A~ Hammock, Cool Drink, Whispering Pines.
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- Don Pedro's Cottage
How many rentals, hotels, or resorts are available in Windward?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 1134 properties listed by Vacation Cottage in the Windward area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Windward.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Rental Cottages and Private Getaways in Florida | 63 |
