Yes, Orlando does have a winter! There are a few months of the year (November, December and January) where the Orlando weather can dip below 75 degrees during the day and some nights (typically less than 5 a year) where the temperatures can border on freezing.
For our international visitors from Europe and Canada and most domestic travelers, these temperatures can still seem incredibly hot for this time of year – hence Florida is the Sunshine State. Winter rentals in Orlando are quite pleasant.
Most single family homes will typically charge a little extra if you want your private pool heated. A small price to pay for true luxury. If you are looking to save money, you can take your chances and not heat the pool. We recommend that you also rent a home in a community with a great community pool. Some of our favorite Orlando area vacation home communities with great community pools include: Windsor Hills Resort Villas, Windsor Palms Vacation Homes and Vista Cay.