Villa holiday rentals in Illinois

Rockford’s Historic Villa + CLOSE to city!

Experience the timeless elegance of Jesse Barloga's renowned architecture from the 1920s at our spacious and centrally located historic residence in Rockford, Illinois. This exquisite Italian Villa, nestled in the charming Brown Hills area near the Rock River, offers unparalleled proximity to the Rock River bike path, YMCA, and Nicholson Conservatory and is close to Downtown life. Immerse yourself in the convenience of accessing the region's finest attractions, many just a short stroll away!

22min to Starved Rock: Ultimate Vacay Villa - 3891

5 Bedroom, 6 Bathroom, Sleeps 16 (Unparalleled Value!) Affordable 5500 sqft. 5 bedroom, 6 bath ultra-private family vacation destination, surrounded by 1.2 acres of mature trees and wildlife, perched hilltop showcasing its gorgeous views overlooking all of Ottawa. You will be just minutes from Starved Rock and Matthiessen State Park. Note: This is a family vacation home not to be used for events or wild parties. Please do not reserve without talking to me first, as it will be auto declined.

Luxury Chicago-Wilmette High End Private Residence

Our Property Is Best Described by Our Guests : 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+ We will be back just ! Thank you!

Copperfield - Unit 1 - 5 Bed/4 Bath

Come stay at one of the coolest vacation rentals in South Central Illinois. Originally built in 1918 by a member of the Kohl family, this building has been a focal point of downtown Centralia ever since. The property features old world architecture, with its solid brick structure and rich woodwork, and spectacular courtyard. Newly remodeled with a fresh look and an old world feel, it is a comfortable place for friends and families to stay. This is the main unit of 2 in the building.

All SeasonVilla-Starved Rock area!

Spacious Vacation Villa in Starved Rock Country. Perfect for getting outdoors, exploring the area or just staying nestled in to enjoy this cozy home. So much to do within 15 minutes or less-hiking at Starved Rock and Matthiessen State Park (all season beauty), canoeing, horseback riding, river cruise, sky diving, fests throughout year and more. Or kick back-eat in, play games, watch movies and relax! Whatever you choose it's a great getaway near Chicago and the suburbs to enjoy.

Coastal Dreamin' near I-57, quiet community!

If you'd rather be at the coast, you'll love this 2 bedroom villa with 2 full, updated bathrooms. Recently renovated with new luxury vinyl throughout. 2 separate living areas with smart TVs, Master bedroom is spacious with a walk-in closet where we've added a dedicated space to get ready. There's also a 1 car garage and laundry room for guest use. Wrap around sectional in the living room and a power recliner. Dining table for 4 inside and patio table out!

Rooftop | Villa

Beautifully renovated luxury residence featuring 3 spacious suites, designer furnishings, antique Murano and Luminaire chandeliers, Young Chang grand piano, new wood flooring, and a spectacular rooftop deck with Lake Michigan views. Family-friendly and ideal for executive or extended stays, the home offers peaceful, elegant living with premium appliances, private terraces, and thoughtfully curated interiors designed for comfort and relaxation.

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp

🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 🎯 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!

Starved Rock Hideaway

Vacation Villa tucked away in Starved rock country adjacent to St. Louis Canyon with a serene setting. Close to the quaint town of Utica which offers antique shopping,wineries,bars,restaurants and horse back ridding. Just beyond Chicago approx 1.5 hour from Ohare and 1 hour from midway. Seasonal bicycle rentals available.

Living the High Life Pool House

Relax with family & friends at our large heated indoor pool with a tiki bar, game room & stylish, cozy living space & kitchen. With tons of gathering space, you can enjoy our home in all seasons. *Hot tub added Feb 2nd*

Scenic South Course Villa, Fireplace & loaded w/St

2 Bedrooms, 2 Baths, Queen Sofa Sleeper in Living Room - Sleeps 4 in beds, Occupancy of home is 6