Luxury rentals in Lake Michigan

Large Luxury House in River North!

Centrally located River North Penthouse in boutique building has everything you would want in city living. 2-story condo ALL 3 bedrooms featuring en-suites and an additional 1/2 bath. Large living room w/fireplace expands on to the outdoor deck with beautiful built-in grill, 2nd story features 2 bedrooms and a bright sun room with sofa bed. Spacious primary cozy fireplace along with steamed shower and jacuzzi tub. So much more with this luxury style living. Steps to all River North has to offer!

Contemporary 26-Acre Estate, Private Beach, Pool

A true vacay dream, this stunning lakefront 26-acre estate has a private beach, gorgeous pool, hot tub, indoor sauna, fabulous 7-bedroom home, and so much more! The lush, spacious open design offers plenty of options for enjoying maximum R-and-R. Living room and family room fireplaces and flat-screen TVs provide chill time, while the Chef's Kitchen island is popular for coffee chats. The formal dining room has fab lake views, as do elegant bedrooms and the posh poolside deck. Life is good here!

Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard.

Blackwood Shores

Experience luxury in this Harbor Country retreat with a heated pool, relaxing hot tub, and easy access to one of the area's best beaches. Lounge by the pool, enjoy sunset soaks and head to the beach for long walks and lakeside lounging. Inside, enjoy a gourmet kitchen with a large island, bright living spaces, a huge screened porch and a lively garage game room for ping pong and fun. Designed for connection, comfort, and relaxed lake living, this home delivers unforgettable vacation moments

Luxury Designer Penthouse|Private Deck|Gold Coast

BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. In a completely redeveloped luxury brownstone, your 3 bedroom/3 bathroom penthouse offers ultra high-end appliances, design, and finishes, with two private patios/decks (truly unique amenity in Chicago) and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between!

Enjoy Bear Ranch, A Premier Luxury Vacation Estate

Bear Ranch offers an opulent vacation in a massive estate with 3 floors of elegance and relaxation. Enjoy cathedral ceilings, abundant natural light, and a stone fireplace. The game room, bar, and movie room offer endless entertainment. The Chef's Kitchen is fully equipped for gourmet meals. With top-tier bedrooms, bathrooms, balconies, a huge pool, 2 hot tubs, grills, a soccer field, and a firepit, this home provides everything you need for an unforgettable stay. Boom.

Ultra Modern Luxury - New Construction 4 Bedrooms

🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, and vibrant dining, shopping, & nightlife. Featuring 4 bedrooms and 2.5 baths, the condo boasts a private rooftop deck with a fire pit 🔥, loungers, and patio seating. Just ½ block to the Red Line 🚇. Garage parking included. Concierge services available. Ideal for short-term stays, executives, or insurance clients. Enjoy comfort & convenience! ✨

Door County Lake House

We are excited to introduce our Architect-designed modern lake house in the town of Clay Banks! Enjoy serenity, sweeping views of Lake Michigan from a secluded back deck & expansive windows from every room in the house. Embrace slower living, waterfront amenities, neighborhood park with trails and the magic of lake life. You’ll enjoy water fun for the whole family, huge back deck with dining for 8, an outdoor lounge area, and fire pit near the water.

1,622SqFt Penthouse | 69th Flr Views | Sleeps 4

Wake up on the 69th floor to the entire Chicago skyline glowing beneath you — inside the biggest 2-bedroom penthouse in the city. At 1,622 sq ft, 'Skyfall' gives your group room most hotels charge four times more for. Hosted by Cloud9 — 4.9 stars across 5,000+ reviews, specializing in luxe penthouse stays. Floor-to-ceiling windows and 80,000+ sq ft of building amenities included. Book the view — and the space — most people only see from postcards.

Hot Tub, Fire Pit & Two Decks - Beach 300 Yards!

Welcome to Sunset on Pokagon! This stunning 2,850 sqft home offers style, comfort, and outdoor fun. With 4 spacious bedrooms, including one with a pull-out sofa and convenient C-Tables for lounging or working in bed, and 2.5 baths. Relax in the new hot tub, gather around the fire pit, or enjoy 1,000 sqft of decks surrounded by nature. Just 300 yards from the beach and local gems, this home isn’t just a stay—it’s an experience!

Luxury PH: Panoramic Views + Prime Location

Temporary housing doesn't have to feel temporary. The Sol, a 4-bedroom penthouse on the 23rd floor in the Chicago Loop, 2,643 sqft of warm, bold, timeless interiors with west-facing views over the city skyline and sunsets. Sleeps 9 across 2 King suites and 2 Queen rooms, with three full bathrooms and a half bath. A real home in a real building, with the same doorman and neighbors as the residents who live here year-round.

Architect-Designed 3BR Oak Park Flat

Experience historic Oak Park in our beautifully renovated 3-bedroom apartment. Blending 1920s charm with modern luxury, this space comfortably fits families or groups. Features a dedicated workspace, new kitchen, and a shared roof deck. Located steps from the Green Line, offering a quick, direct ride to downtown Chicago. Perfect for exploring both Oak Park's cultural gems and the Windy City.