Windward Accommodations - Hotels & Rentals
About Windward Vacation Rentals
Discover More than 1161 Incredible Getaway Rentals Available in Windward. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Windward.
Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Windward, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Windward. The Average Size of Places to Stay Near Windward is 1040.59 ft², with Prices Averaging US $340 per Night.
Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Windward. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.
Top Hotels & Vacation Rentals in Windward
| Type | Count |
|---|---|
| Vacation Homes | 818 |
| Villas | 148 |
| Holiday Apartments | 31 |
| Cottages | 18 |
Use these Quick Filters to Find a Vacation Rental in Windward
★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Windward with Online Reservations.
Weather in Windward, FL
View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Windward?
What are the top hotels, lake houses & vacation rentals in Windward?
We provide an array of great vacation destinations in Windward. If you are looking to stay in or around the Windward area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals 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
- 'Incommunicado ' ~A~ Hammock, Cool Drink, Whispering Pines.
- A Little Slice of Paradise
- Your serene escape - Modern, cozy, and close to the beach.
- Don Pedro's Cottage
How many Hotels & Vacation Rentals have private pools in Windward?
We have 430 Hotels & Vacation Rentals featuring a private pool in and near Windward. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel, lake house, or vacation rental in Windward is best for families?
Searching for a family-friendly getaway in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Heated pool with canal views
- Walk to Marina: Placida Condo w/ Community Perks!
- Palm Island 2 Bedroom Superior Villa by RedAwning
How many hotels, resorts, or rentals are available in Windward?
Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 1161 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Windward.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Vacation Rentals in Florida | 66 |
