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1060+ The Loop Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near The Loop

Discover more than 1060 StayAndPlay accommodations in The Loop, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near The Loop, IL.

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 The Loop? 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 The Loop pet-friendly golf accommodations and easily book your dream golf resort or villa rental in The Loop with StayAndPlay.

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Frequently Asked Questions About The Loop Holiday Rentals

There are a lot of options in The Loop. If you plan on staying in the The Loop 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 The Loop:

There are many holiday rentals available in The Loop; however, here are a few of the most popular holiday homes listed in The Loop on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in The Loop to find one that works for you.
Yes, there are 1060 self-catering family homes and holiday rentals in The Loop.
There are more than 1060 luxury holiday homes in or near The Loop, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 1060 pet friendly rentals that are available in The Loop.