Villa holiday rentals in Cook County

Luxury Chicago-Wilmette 5 BR/5B

Our Property Is Best Described by Our Guests : LS 09/27/23-10/27/23 5/5 Amazing location and space to breathe We needed a long term place to stay, and wanted a place to LIVE. We needed a home and this was the perfect answer. Located in a beautiful safe neighborhood, literally minutes from the lake, from Old Orchard mall, grocery stores, and everything else we needed. Only a 5 minute drive to a park and ride for the train. Very quiet despite proximity to everything. Perfect 10+

Rooftop | Villa | Events

Gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Party Backyard/Rooftop Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: Three 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.

Chic ART|12Guest|3BR|Home360Roof+HotTub|CarGarage

🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 ✅DM for YOUR SPECIAL RATE! 🎯 Free Private Garage 🎯 Hot Tub 🎯 360° Roof Deck with Skyline + Willis Tower Views Perfect for family trips, romantic escapes, or friend getaways! ✨ Private keyless entry 🛏 Luxury KING, 2 QUEEN beds + cozy fireplace 🍽 Full kitchen + balcony 📺 3 Smart TVs (Netflix, Disney+, Prime) 🚀 Super-fast WiFi Book now for your unforgettable Chicago stay!

Private Room in Equestrian Villa

Relax at this peaceful Equestrian villa.

2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking

2 Queen Beds | Micfridge

2 Queen Beds | Micfridge

2 Queen Beds | Micfridge

2 Queen Beds | Micfridge

1 King Bed | Micfridge

1 King Bed | Micfridge