Luxury rentals in Lake Michigan

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!

NEW 1BR Cottage with Pool, Firepit, Walk to Beach

Presenting Townie 1 - The Ivy, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

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! ✨

Fab Vacay Home, Pool, Walk to Lake Michigan Beach

This fabulous 6BR/4BA beach house will WOW you with its blend of elegance and comfort, just steps from a superb beach and amenities. Enjoy the chic open design of the Chef's Kitchen, Dining Room, and Living Room, with views of the courtyard, pool, and deck. Gorgeous, comfy bedrooms and designer bathrooms make living easy. High-end furnishings inside and out, with a dose of relaxing Zen beauty throughout. Vacay Heaven is yours—R-and-R, boom!

Hot Tub, Fire Pit and Zen Garden Paths

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.

Entire mansion for 18 guests with indoor pool!

Escape to your private oasis at our serene Lake Michigan retreat! With abundant amenities and breathtaking surroundings, it's ideal for family vacations, corporate events, and more. Enjoy the peaceful countryside setting, explore nearby golf courses in Kohler like Whistling Straits, or simply relax by the pool. Can comfortably accommodate 18 guests.