Illinois Vacation Homes and Villas with Pools

Swimming pools are a great way to cool off during the hot summer months or to enjoy a relaxing soak after a long day of activities. At PickleTrip™, we offer a wide range of vacation rentals with swimming pools in Illinois to suit all types of travelers. Whether you are looking for a private pool for a family vacation, or a communal pool to share with other guests, we have something for all pickleball enthusiasts and every traveler.

Our vacation rentals with swimming pools come in all shapes and sizes to suit your needs and budget. From luxury villas with private infinity pools to cozy cabins with communal hot tubs, our rentals have something for everyone. We also offer a range of amenities such as WiFi, hot tubs, self-catering, and more to make your stay as comfortable as possible. Browse our selection of vacation rentals with swimming pools in Illinois and book your next vacation today!