Villa holiday rentals in Chicago

Find and book unique villas on Airbnb

Top-rated villa rentals in Chicago

Guests agree: these villas are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 2 pages

Superhost

Villa in West Town

5 out of 5 average rating, 3 reviews

✅DM for YOUR SPECIAL RATE! 🎯Private Garage (FREE) This home comfortably accommodates up to 12 guests, ideal for romantic getaways, family reunions, or gatherings with friends! With private keyless entry and a car garage, check-in is seamless and hassle-free. ✅Luxury KING bed ✅2 Queen beds, Fireplace ✅Fully stocked kitchen with a balcony. ✅3 Smart TVs plus Netflix, Disney+, and Prime streaming. ✅Super-fast WiFi ✅Roof deck: Incredible views of the Chicago Skylights and Willis Tower. ✅Pets

Superhost

Villa in Westmont

4.8 out of 5 average rating, 45 reviews

Westmont,Il Duplex - Side B. In law suite 1/1

Check out video walkthrough. This is a small apt with private entrance. It is part of a larger house that is also rented. There is no stove just a hot plate and a large counter top oven. There is a kitchen sink. Living area is two chairs. There is a private deck with a beautiful view of the lake. The yard and driveway are shared. There is potential to hear people next door. Currently no control over heat or AC. We keep at reasonable temp 68-75 and give a separate heater and fan.

Villa in South Shore

4.63 out of 5 average rating, 52 reviews

Rooftop | Villa | Parking

Meet up with group at this gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: 3 levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record