Enjoy an upgraded stay with total privacy in Chicago. Browse exclusive villas and vacation homes equipped with individual, private swimming facilities. Compare verified options on Owner Direct for a peaceful, secluded getaway.
Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering
Fabulous
3 reviews
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Exceptional
2 reviews
Apartments, Luxury, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family
Superb
17 reviews
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Exceptional
11 reviews
Wellness Facilities, Tv, Business Services, Barbecue/Outdoor Cooking, Security/Safety, Entertainment, Guest Services
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Fabulous
2 reviews
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Good
1 reviews
Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering
Very Good
30 reviews
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Good
1 reviews
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
5 reviews
Guest Services, Air Conditioner, Security/Safety, Entertainment, Internet, Tv, Pet Friendly
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
Apartments, Cheap, Accommodations, Pools, Serviced apartments, Pet-friendly, 3-star, Lodgings, Vacation rentals
Fabulous
2026 reviews
Apartments, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Family
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs, Places to stay
Good
4 reviews
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals
Fabulous
20 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Chicago.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our vacation rentals with private pool stand out?
Every vacation rentals with private pool shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best vacation rentals with private pool in Chicago are:
There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals wint Private Pool in Chicago
You can explore 26 verified vacation rentals with a private pool in Chicago. These include standalone villas and private homes where the pool is reserved exclusively for your group.
Prices for rentals with a private pool in Chicago vary depending on the property size, location, and travel season. Rates typically start from around $87 per night, with higher prices for larger homes, prime locations, or peak travel periods.
Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.
Yes, some vacation rentals with private pools in Chicago also welcome pets. Currently, 19 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.
Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.
Vacation rentals with private pools in Chicago often include additional features such as Private Pool, Pool, and Internet. These amenities enhance comfort and create a more relaxing, self-contained stay.
Some family-friendly vacation rentals in Chicago include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.