1. USA
  2. Florida
  3. Orlando
  4. Windermere
  5. Cottage Rentals

Windermere Cottage Rentals & Golf course

Find the best cottages in Windermere - We found 53 exact matches

About Windermere Cottage Rentals on StayAndPlay

Looking for exceptional golf cottages near Windermere for your next getaway? StayAndPlay offers more than 53 unique golf retreats and luxury villas, perfect for your family or group trip. Discover accommodations set in scenic golf destinations, featuring amenities like private pools, championship course access, and spacious living areas. These rentals provide an exceptional experience, catering to families, friends, couples, or golf enthusiasts.

Planning a golf retreat or a getaway for your group? StayAndPlay provides a variety of accommodations, including top-rated golf cottages, private villas, and spacious vacation rentals, connecting you directly with property owners to secure the best rates.

Explore 53 premium golf stays and exclusive golf-friendly accommodations in Windermere with StayAndPlay. Find unique Airbnb-style and VRBO-style golf rentals perfect for your weekend escape, golf vacation, or corporate retreat, all within your budget.

Show more
Show less

Frequently Asked Questions About Windermere Rental Cottages

There are a lot of options in Windermere. If you plan on staying in the Windermere area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windermere:

The average cost for a cottage rental in Windermere is $405 per night. StayAndPlay.com has a wide list of great cottages near Windermere that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Windermere that allow you to bring your pet:

See all pet-friendly vacation rentals in Windermere on StayAndPlay

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windermere to find one that works for you.
As of 2025, the data from StayAndPlay shows that there are Over 53 private swimming pools or cottages with indoor pools in the Windermere area along with other great amenities.
About 53 cottages in Windermere boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Windermere on StayAndPlay
Yes, there are luxury cottages in Windermere. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windermere.