Luxury rentals in Lake Michigan

Landmark Home 1 Blk from Lk MI w/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. This property has been selected for inclusion in The 100 Collection, a global designation awarded to only the top professionally managed vacation rentals based on consistent quality and service. Classy, awe-inspiring, and sumptuous, this 1928 4 BR/2.5 BA vacation home, located just a block from Lake Michigan in “Harbor Country,” was once a local retail gathering place. Recently refurbished into a stunning residential home, it includes gorgeous reclaimed flooring from antique beams, custom doors, light fixtures, and hardware, as well as top-of-the-line plumbing fixtures. The kitchen-dining room-living room area—a massive, superbly well-lit space—features entire walls of French windows, original glass-block, and a wide array of seating options for meals: 4 chic stools at the white marble island, 4 leather seats around a circular marble coffee table, and a 10-seat reclaimed wood dining table. The beautifully lit living room has a classic stone fireplace at its center, stylish (yet ultra-comfortable) couches and chairs, and a wide-screen TV. In addition to the three bedrooms and bathrooms on the ground floor, there’s a second-floor sleeping loft, perfect for kids with cute bunk beds and a real (mini) teepee. All bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and your guests. Black Door Bungalow can sleep up to 10. MAIN FLOOR Primary Bedroom: 1 King bed Bedroom 2: 1 Queen bed Bedroom 3: 1 Queen bed UPSTAIRS FLOOR Bedroom 4: Full-over-full bunk bed that sleeps 4 Another “extra” is the detached garage, which has been turned into a posh game room, with high-end shuffleboard and foosball tables, a big-screen TV, and a sound system. The exterior—featuring a spacious covered patio with cozy rattan couch, chairs, and a 4-seat dining table, leading to a bluestone courtyard—has been extensively landscaped with lush plantings, trees, and professional lighting. The home also includes a high-end kitchen, EV charger, and laundry appliances. In addition to being an easy walk from a majestic, crystal-sand Lake Michigan beach—and a super-short drive to popular beaches like Pier Street Beach and Cherry Beach—you and your guests can also enjoy the many activities afforded by being near Warren Woods State Park, which offers all sorts of woodland hiking and biking trails. The region’s largest recreational harbor provides countless water-related excursions and rentals, from fishing trips to boat, kayak, jet-ski, and paddleboard rentals, as well as day and evening cruises. There’s also the Acorn Theater, a local treasure for live performances by nationally recognized music artists, and a number of nearby breweries, wineries, brew pubs, and even an award-winning distillery for you to check out. Of course, you and your guests can also enjoy sampling to your heart's content the many popular restaurants, cafes, art galleries, boutiques, and antique shops just a hop, skip, and a jump away in Union Pier and downtown New Buffalo.

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 6-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!

Champions Point Legendary Living

Live like a legend at 2700 Point Ln! This estate was built with privacy, security, and luxury in mind - a private oasis on 7.39 acres surrounded by mature pines, fenced and gated. Enjoy putting on your professional grade putting green, fishing in your private pond stocked with bass and bluegill, and swimming in your zero-entry infinity edge pool! Inside enjoy your movie theatre, commercial gym, cigar lounge, wine cellar, pool tables, bars, salon, salt water aquariums, and full basketball court!

Family Luxury Lakefront Sunsets • Beach • Golf

Welcome to Pigeon Lake Luxury. A private beach estate near Lake Michigan. Sunset decks, family-ready amenities, and peaceful water views meet five-star stillness. Fully stocked with beach gear, baby items, and luxe touches. Designed for rest. Built for memories. Includes private beach parking, toddler gear, high chair, coolers, towels, boardwalk access, and concierge-level hospitality. Ideal for family retreats, peaceful escapes, luxury vacations, romantic stays, and unforgettable lake days.

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 w/ 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!

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.

PH w/ Bean & Lake Views, An Elite Stay

For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The Bean & Millennium Park views and access to a private amenity floor. It's a proven elite experience, with a remarkable 9 out of 10 recent guests leaving a 5-star review.