Holiday rentals with a pool in Lake Michigan

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Top-rated rentals with a pool in Lake Michigan

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.
Flat in Chicago
4.9 out of 5 average rating, 565 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Top guest favourite
The outdoor area features a private hot tub with illuminated water, surrounded by trees. A wooden deck leads to a fire pit area with seating and a propane grill nearby. The serene lake reflects the surrounding nature, creating a peaceful ambiance.
Cottage in Gaylord
4.97 out of 5 average rating, 154 reviews

Hot Tub, Wood Stove, Close to Skiing, Trails, Snow

Welcome to Greenhouse Cottage! Relax in this lakefront home on all-sports Buhl Lake! This home is newly updated, professionally decorated & ready to host your favorite travel memories. Just under 20 min from Treetops & Otsego and under 30 min from Boyne & Schuss ski resorts for all your downhill thrills! Trail 4 Access. Mod furniture, hot tub, wood stove, fire pit, kayaks, paddle board, outdoor heated pool (Summer only), and ATV Trails await. Your ideal home away from home is waiting for you!

Top guest favourite
An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.
Guest suite in Gary
4.98 out of 5 average rating, 112 reviews

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Top guest favourite
Two blue mugs are positioned on a wooden railing, overlooking a sandy beach and Lake Michigan. In the distance, the Frankfort Lighthouse stands tall against a clear sky, creating a serene coastal view.
Apartment in Frankfort
4.99 out of 5 average rating, 157 reviews

"THE NEST" Condo on Lake Michigan Lighthouse View

Welcome to THE NEST" Condo with direct gorgeous views of the Frankfort iconic Lighthouse with sunsets on the sandy beaches of Lake Michigan at Harbor Lights Resort. Definitely a world class view for you! A quick 2 block stroll to the quaint downtown Frankfort Enjoy a quiet night's sleep in a very large bedroom with two comfy, queen sized beds. Up north style Livingroom with featured gas fireplace Large deck with open view of beautiful Lake Michigan Heated Pool and relaxing hot tub available

Top guest favourite
Place to stay in Crystal Lake
5 out of 5 average rating, 127 reviews

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

Top guest favourite
A serene view of a marina features several sailboats and motorboats docked along the water's edge. Lush green landscaping surrounds the area, with trees providing a natural border. A calm lake reflects the nearby buildings, creating a peaceful atmosphere.
Apartment in Manistee
4.99 out of 5 average rating, 180 reviews

Water view, Lake Michigan Oasis

NOTE: indoor pool closed 10/2/25-11/17/25. Welcome to our relaxing water view home! You are a short walk from Lake Michigan and nearby hiking trails. Relax inside by the fireplace while doing a puzzle with views of water from all windows. Our community includes access to an indoor pool and hot tub, open 6a-10:30p daily year round, and an outdoor pool in the summer. Two queen bedrooms + extra landing space with full/twin trundle allow for many to sleep. Fully stocked kitchen and laundry.

Guest favourite
An indoor Endless Pool is framed by wooden paneled walls and large windows, allowing natural light to fill the space. A stone-tiled floor leads to the water with a railing for entry. Adjacent, a spa area is visible, enhancing the relaxing environment.
Home in Midland
4.97 out of 5 average rating, 291 reviews

Indoor Infinity Pool - Outdoor HotTub - Sauna

This home was created for my wife (Sarah) after we received difficult news of her cancer diagnosis (Ewing Sarcoma) while pregnant. We were able to create an uplifting environment to support her as she battled courageously. Unable to leave the home much, we decided to bring life's beauty to her within the home and around the property. Sarah was the ultimate host who loved to bring people together. We now visit for my little kids to remember their mom. We hope you enjoy it as much as we do!

Top guest favourite
A comfortable living area features a spacious gray sofa facing large windows with unobstructed views of the water. Natural light floods the space, accentuating a round coffee table made of woven material and a dining table with chairs near the window.
Apartment in Traverse City
4.99 out of 5 average rating, 138 reviews

Stunning Waterfront, Updated TC Condo with Pool!

Have this updated, waterfront condo be your home away from home while visiting the Traverse City area! This condo sits on East Bay with unobstructed views of the water. In the summer, hang poolside between exploring Traverse City hot spots. This condo offers one bedroom with a King bed with an additional queen sleeper sofa in the living room. Full kitchen is perfect for making up any meal and enjoying it on the balcony overlooking the water. Long day of hiking? Soak in the complex hot tub.

Top guest favourite
Home in Cleveland
4.97 out of 5 average rating, 117 reviews

Malibu House | Luxe Lakefront Escape w/Indoor Pool

Malibu House | Luxe Lakefront Escape w/ Indoor Pool 🌊 Private 7,000 sq ft Lake Michigan estate 🏖️ Direct beachfront access — “Malibu of the Midwest” 🏠 6 ensuite bedrooms | sleeps 14 guests 🎬 Private movie theater & epic game room 🏊‍♂️ 45-ft indoor pool + 85” TV lounge 🔥 Chef’s kitchen & 20-ft fireplace views 🏌️‍♂️ Minutes to Whistling Straits & Kohler Resort 💎 A Wisconsin Getaways exclusive experience Book NOW and be prepared for your loved ones to call you the BEST EVER!

Top guest favourite
A spacious bedroom is presented with large windows overlooking lush greenery. An inviting bed adorned with a patterned quilt is complemented by wooden furniture, including a dresser and mirror. A cozy seating area is visible next to the fireplace, creating a warm atmosphere.
Apartment in Bellaire
4.96 out of 5 average rating, 224 reviews

Lakeview 🌅 Fireplace, Walk to Summit GC & Pools ⛳️

This 1 bedroom, 2 bed, 1 bath 605 sq. ft. condo sleeps 4 and is located in Summit Village. The condo features a full kitchen, wood burning fireplace, queen sleeper sofa, and private deck for stunning Lake Bellaire sunsets. Your stay includes access to the resort’s multiple indoor and outdoor pools and the indoor hot tub. Our condo is a short walk to the Summit Golf Course, Shanty Town and the Lakeview Restaurant. Staying here means you're right in the heart of Shanty Creek Resort!

Guest favourite
Chalet in Gaylord
4.96 out of 5 average rating, 241 reviews

Bear’s Den ~ Hot Tub, 2 Pools,Kayaks,Skiing&Trails

Leave your worries behind at this spacious and charming 3-bedroom chalet, set on a peaceful lake with a private outdoor hot tub. Just 6 miles from downtown Gaylord, this Alpine retreat is perfect for year-round family fun. Spend your days kayaking, swimming, fishing, or barbecuing on the deck, then unwind on the dock or soak in the hot tub as the sun sets over the water. Whether summer adventures or snowy getaways, this lakefront chalet is the perfect Up North escape.

Top guest favourite
A cozy seating area features a gray sofa adorned with decorative pillows and a small pouf. Natural light streams through a wall of windows, offering views of the lush landscape. A wall-mounted television is positioned nearby, enhancing the relaxing ambiance.
Apartment in Manistee
4.99 out of 5 average rating, 143 reviews

Clean & Cozy Lake MI Studio w/ Water Views

Escape & unwind at this Lake MI studio condo. Perfect for adventurers, couples, or small family looking to getaway to the coast in a space that blends tranquility, convenience, & warm hospitality. The condo was lovingly curated with details to make your stay special & provide an elegant yet charming feel. Enjoy water views, superb hosting, & an exceptional location near condo amenities, Lake MI, Manistee’s Historic downtown, & much of what West MI has to offer.

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