Windward, Placida holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Windward that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windward

Lay out by the pool and enjoy the nature preserve like view!

Spanish Villa with Pool overlooking golf course

Sleeps 9 · 3 bedrooms · 2 bathrooms

Harborfront Condo (Only 26) PRIVATE sandy beach! Boat activity view from lanai

Sleeps 4 · 1 bedroom · 1 bathroom

Gorgeous and quiet condo with pool, lanai, golf, balcony, washer/dryer, & WiFi

Sleeps 7 · 2 bedrooms · 2 bathrooms

SPECIAL summer prices! message for us for rates. Charming pool home in Coral Caye

Sleeps 6 · 3 bedrooms · 3 bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Windward?

Season, length of stay and property type are some factors that can determine the price of a holiday home. Simply click on your dates of travel to find your ideal fit. From comfy cottages to sprawling luxury villas, all Stayz holiday homes offer unbeatable value.

How much does it cost to rent a beach house in Windward?

When you travel and the size and style of the property will help determine the cost of your beachside escape. Put in your Windward travel dates to view your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the features and amenities you want.

What are the top attractions for families in Windward?

Keep your kids occupied at these popular family-friendly attractions in Windward:

Little Gasparilla Island Beach
Don Pedro Island Beach
Don Pedro Island State Park

How old do you have to be to rent a holiday home in Windward?

The minimum required age is typically 16, 18 or 21. It can vary across properties on Stayz, so look at the rules of your preferred Windward holiday home before booking your stay.

How long can I rent a holiday home in Windward for?

It's really down to the Windward property. To view a list of options offering extended stays, just enter your dates and number of people into Stayz's search page. Look forward to having the whole property to yourself, as well as comforts such as a kitchen, air conditioning and a yard where the kids can run and play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.