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32+ Middlesboro Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Middlesboro

Discover more than 32 StayAndPlay accommodations in Middlesboro, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near Middlesboro, KY.

Whether you're seeking upscale golf-front resorts, private luxury villas, spacious vacation homes, or family-friendly golf retreats, we can help you find the ideal stay. Our rentals feature top-tier amenities such as private pools, fully equipped kitchens, outdoor patios, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group golf trip to Middlesboro? StayAndPlay guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Middlesboro pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Middlesboro with StayAndPlay.

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Frequently Asked Questions About Middlesboro Holiday Rentals

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

There are many holiday rentals available in Middlesboro; however, here are a few of the most popular holiday homes listed in Middlesboro on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in Middlesboro to find one that works for you.
Yes, there are 32 self-catering family homes and holiday rentals in Middlesboro.
There are more than 32 luxury holiday homes in or near Middlesboro, according to 2026 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 32 pet friendly rentals that are available in Middlesboro.