Vacation rentals with a pool in Michigan City

Guesthouse in Merrillville

A private outdoor gazebo houses a spacious jacuzzi, accompanied by soft lighting and a view of the surrounding greenery. Nearby, a wooden deck features a dining area with a table and chairs, inviting relaxation in a peaceful setting.

4.94 out of 5 average rating, 139 reviews

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

4.97 out of 5 average rating, 100 reviews

A two-story house features a vibrant blue exterior with a spacious porch equipped with rocking chairs. A golf cart is parked in the foreground next to a white picket fence. Clear skies and sunlight enhance the inviting and serene atmosphere.

Home in Michigan City

Beach Nest, Sleeps 20, 5 min. to Lake Michigan.

Beach Nest is a place to relax!! Minutes away from beautiful Lake Michigan. About 1 Hr. away from Chicago Midway and O'Hare airports and Downtown and going east... Notre Dame Football Stadium. Amenities incl. Outdoor Pool, Tennis, Basketball Courts, Putting Green. Paddleboards and Kayaks on Lake Kai. Indiana Dunes National Park, Michigan City Zoo are 10 Minutes away as well as Blue Chip Casino. Horseback riding, Skydiving, Great eateries, Art Galleries. Come and have fun with Family and Friends!

5 out of 5 average rating, 203 reviews

The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.

Home in New Buffalo

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

4.82 out of 5 average rating, 746 reviews

An aerial view captures the inviting pool area surrounded by lush greenery. The sparkling blue pool is framed by several lounge chairs, with a shaded patio leading to a well-maintained RV parked near the entrance. Colorful landscaping adds to the serene outdoor setting.

Camper/RV in Porter

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

4.95 out of 5 average rating, 218 reviews

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

4.95 out of 5 average rating, 105 reviews

An outdoor firepit area is surrounded by teal-colored Adirondack chairs, creating a cozy space for gathering. The house features multiple windows illuminated at dusk, highlighting its charming architecture, while trees provide a natural backdrop, enhancing the outdoor setting.

Home in New Buffalo

NB Getaway w/HotTub,Pool,BBQ & Priv Screening Room

Richly designed 6BR/5BA home near New Buffalo Harbor and beaches. Great Room with stone fireplace. Chef’s kitchen with marble-top island. 3-season sunroom. Elegant, comfy furniture. Primary BR with stone fireplace, twin sinks, tile walk-in shower, and jacuzzi. Lower-level Guest BR with fireplace, full BA, game room, and screening room. Second floor features loft space, 3 BRs, 2 BAs, and a Mother-in-Law Suite with kitchen. Smart TVs in 5 BRs. BBQ deck, firepit patio, and hot tub.

4.96 out of 5 average rating, 224 reviews

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

4.97 out of 5 average rating, 126 reviews

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

4.99 out of 5 average rating, 105 reviews

The charming exterior of the home showcases a vintage orange convertible parked beside a motorbike, set against a lush backdrop of greenery. The gravel path leads to a welcoming entrance surrounded by tall trees and vibrant foliage.

Home in Three Oaks

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Autumn at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. Equal parts sanctuary and playground, this designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

4.98 out of 5 average rating, 172 reviews

A fenced-in pool area features a clear water pool surrounded by a concrete deck. Lounge chairs and a dining set are positioned nearby, while a red umbrella offers shade. A slide is visible in the pool, with cornfields extending in the background under a cloudy sky.

Guesthouse in Cassopolis

Country cottage with hottub for two!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

Guesthouse in Michigan City

The exterior of Lagunitas Coach House is shown, featuring a screened-in porch with two red chairs. Lush greenery and flowers surround the entrance, while a small table rests beside the chairs. A clear blue sky provides a bright backdrop.

4.86 out of 5 average rating, 163 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

4.92 out of 5 average rating, 115 reviews

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

Home in Michigan City

Beautiful home with Beach views in Beachwalk

Enjoy the open concept family room/dining area, flat screen TV, fireplace, and a farmhouse table that seats 12. You can also enjoy the sunset from the top floor "birds nest" with views of the Chicago skyline. The lower level is perfect for kids to watch TV and play games and is equipped with bunks that sleep up to 7 people. A Staircase leads to a private walkway for access to Lake Michigan.

Popular amenities for Michigan City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 12 reviews

Home in Dowagiac

Fall Escape w/Game Room near Wedding Venues & ND

4.95 out of 5 average rating, 21 reviews

The cabin features a wooden exterior with a large covered porch that spans the front. Surrounded by lush greenery, the expansive lawn leads up to the structure, creating a natural and serene setting perfect for outdoor activities.

Home in Union Pier

Private Cabin Retreat - Heart of Harbor Country

4.92 out of 5 average rating, 13 reviews

A bright and spacious backyard features a private pool surrounded by a wooden deck. Comfortable lounge chairs are arranged poolside, with a three-season porch visible in the background. Green grass frames the pool area, enhancing the outdoor relaxation space.

Home in Bridgman

The Poolside Escape | Hot Tub | Arcade | Ping Pong

4.99 out of 5 average rating, 89 reviews

A charming ranch-style house is situated on a spacious green lawn, surrounded by mature trees. The front features a welcoming porch with seating, and a driveway leads to an attached garage on the right. Lush landscaping enhances the tranquil setting.

Home in Sawyer

Fall Fun | Quiet Area | Huge Fenced Yard

4.92 out of 5 average rating, 104 reviews

A modern dining area features a wooden table surrounded by sleek black chairs. Behind it, a vibrant mural of South Bend adds color to the space. A cozy living area with a large sectional sofa and ample natural light can be seen through the open layout.

Home in South Bend

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

5 out of 5 average rating, 26 reviews

A large heated pool is surrounded by a spacious patio and lush green trees. Two lounge chairs are positioned on one side, and a patio umbrella is visible nearby. The area is enclosed by a fence, providing a sense of privacy.

Home in Lakeside

Private! Warren Woods Pool Retreat

4.91 out of 5 average rating, 307 reviews

A game room features a multi-game table for pool, air hockey, and ping pong, surrounded by comfortable bean bag seating. Bright, geometric lighting enhances the space, while classic arcade machines and a large wall Connect 4 game add fun to the cozy environment.

Home in South Bend

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

5 out of 5 average rating, 6 reviews

A designated fire pit area is surrounded by a circle of colorful chairs, set against a sandy backdrop. Green shrubbery provides a natural border, while Lake Kai is visible in the distance, enhancing the inviting outdoor setting.

Home in Michigan City

Nestled on Lake Kai, Perfect for Family Vacations

Condo rentals with a pool

4.73 out of 5 average rating, 11 reviews

A screened-in porch features a wooden circular table accompanied by four matching chairs. A cozy seating area with blue cushions and decorative pillows is also present. Natural light filters through the surrounding trees, enhancing the serene atmosphere.

Condo in Union Pier

Union Pier Condo with Association Heated Pool.

4.7 out of 5 average rating, 10 reviews

A screened-in porch is equipped with a large dining table surrounded by six chairs. Two lanterns are positioned on the table, enhancing the space's functionality. The porch features a blend of natural light and green walls, with a comfortable seating area for relaxation.

Condo in Union Pier

(2026 OPEN!) Union Pier Condo With Heated Pool.

5 out of 5 average rating, 5 reviews

An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.

Condo in New Buffalo

Fall 2 nt min Perfect Location Condo Pools Walk to

4.97 out of 5 average rating, 35 reviews

A spacious deck is shown, featuring a wooden table with an umbrella and string lights illuminating the area. The view of the ocean is visible in the background, with a sunset casting soft colors in the sky. The side of the building is also visible, with multiple windows.

Condo in Coloma

Amazing Beach Condo with pool and great sunsets!

4.94 out of 5 average rating, 93 reviews

A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.

Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.6 out of 5 average rating, 5 reviews

A covered patio area features two chairs overlooking a marina with docked boats. Hanging ferns provide greenery, while a table adorned with a floral arrangement and a blue tablecloth adds a pop of color. The sky is partly cloudy with hints of blue.

Condo in New Buffalo

New Buffalo Condo with Association Pool and Beach!

4.98 out of 5 average rating, 50 reviews

An aerial view of a resort area by Lake Michigan showcases several chalet-style buildings arranged around a spacious parking area. Lush green trees line the shoreline, and the calm water reflects the natural surroundings, emphasizing a serene environment. A sandy beach is visible nearby.

Condo in Stevensville

Sunset Pointe Chalet #31: Beach+ Pool + Games

5 out of 5 average rating, 63 reviews

An aerial view captures a cluster of charming chalets arranged in a semi-circle along the shoreline. The surrounding lush greenery and open parking area enhance the setting. Nearby, amenities such as pools and recreational spaces are visible, blending nature with community living.

Condo in Stevensville

Sunset Pointe Chalet #32: Beach + Pool+ Sports

Other vacation rentals with a pool

5 out of 5 average rating, 3 reviews

Townhouse in Union Pier

Luxe by the Lake | Pool Access | Near Downtown and

5 out of 5 average rating, 26 reviews

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. An island with bar stools is centered, complemented by pendant lighting. Large windows offer a view of the outdoor area, allowing natural light to enhance the space.

Home in New Carlisle

Luxury home with pool.

Townhouse in Saint Joseph

A spacious balcony features a small table and chairs, overlooking a serene marina. The sun shines brightly on the water, reflecting off the surface, while the surrounding docks and distant buildings create a tranquil atmosphere.

5 out of 5 average rating, 8 reviews

Marina Sunset: Savor Fall Flavors in Saint Joseph

4.85 out of 5 average rating, 74 reviews

A clear view of the pool area is presented, showcasing a refreshing blue pool surrounded by a concrete patio. Lounge chairs and a dining set with an umbrella are positioned nearby, while a trampoline is visible in the background. The house features a deck with steps leading down to the pool.

Home in Saint Joseph

Updated 3 bdrm house w/ pool near beach & country

4.97 out of 5 average rating, 31 reviews

An outdoor lounge area features a sectional sofa surrounding a circular table. A pool is visible in the background, alongside colorful pool floats. Orange umbrellas provide shade over the seating, while green grass and paved pathways enhance the space's appeal.

Home in Buchanan

Buchanan Pool House 2 King Beds 25 min to ND

5 out of 5 average rating, 25 reviews

An aerial view captures the chalet community set along a serene shoreline, featuring a series of triangular-roofed buildings arranged nearby a clear blue waterway. Lush greenery surrounds the area, contributing to a tranquil lakeside atmosphere.

Cabin in Stevensville

101 is all the fun! Arcade + Pool + Beach

5 out of 5 average rating, 25 reviews

A serene walkway is encircled by lush greenery and vibrant foliage, leading up to a charming house with large windows. A brick path gently winds through the garden, while a fence creates a sense of privacy. Outdoor seating is visible, inviting relaxation amidst the greenery.

Guesthouse in South Bend

Enchanting Pool House (2.2 miles from Notre Dame)