Winter Garden villa rentals

We found 5,936 villa rentals — enter your dates for availability

Find spaces that suit your style

  • 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 stay in a villa rental in Winter Garden?
Prices vary depending on length of stay, time of year and exact property location, so key in your trip details to check out what's available. Whatever your budget or plans, Stayz has villa rentals in Winter Garden for every kind of guest.
When is the best time to rent a villa in Winter Garden?
The best time to visit Winter Garden depends on factors like activities that you want to do and your favourite season. With average temperatures ranging between 14ºC and 23ºC, February is a popular month to book a villa rental in this part of Orange County. Want to really experience the culture and community of this destination? Check for any local events or festivals and organise your villa rental stay around them.
Where can I rent a Winter Garden villa with great views?
Book a villa rental in Winter Garden and you'll be getting out of bed to amazing vistas. Some of our more popular villas in this destination boast views of historic areas.
Can I book a luxury villa in Winter Garden?
Equipped with an array of amenities like swimming pools, elegant courtyards and modern technology features, Stayz's stylish villa rentals in Winter Garden offer a high-end travel experience. You can expect the finest in comfortable furnishings, ample room and an atmosphere that ensures a relaxing getaway for you and your guests.
What are the top things to do in Winter Garden?
It's easy to see why many families love Winter Garden, with cool attractions like Universal Studios Florida, Magic Kingdom® Park and Orange County Convention Centre to explore. Discover this destination's wonders together and then return to the comforts of your villa rental.
Why should I book my villa holiday with Stayz?
With 24/7 customer support, your peace of mind is guaranteed when you book through Stayz. From the second you lock in your villa rental to even after your stay is over, we're with you at every turn. It's all part of our Book with Confidence Guarantee. What's more, we also have an easy and secure payment process and flexible cancellation policies