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.

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!

4.88 out of 5 average rating, 135 reviews

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

Harbor Country Charm w Heated Pool Open Til 10/12!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

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.

4.96 out of 5 average rating, 184 reviews

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

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, 225 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.

4.98 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, 27 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.

5 out of 5 average rating, 12 reviews

Home in Dowagiac

Fall Escape w/Game Room near Wedding Venues & ND

4.93 out of 5 average rating, 28 reviews

A spacious outdoor pool is surrounded by a black metal fence, offering a sense of privacy. Lush greenery and trees create a natural backdrop. Two lounge chairs are positioned near the pool, inviting relaxation under the shade of nearby foliage.

Home in Three Oaks

Beautiful, sunny 4 BR home with pool and hot tub

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

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

5 out of 5 average rating, 23 reviews

An indoor pool area is illuminated by soft lighting, creating a calming atmosphere. A slide and a basketball hoop are visible by the pool. A plush seating area is arranged along the poolside, with a television mounted on the wall opposite. Indoor plants add a touch of greenery.

Home in Goshen

Indoor Pool Oasis - perfect for large groups

4.87 out of 5 average rating, 15 reviews

A spacious living area features a light grey sectional sofa oriented toward a stone fireplace. Natural light fills the room through large windows, and built-in shelves display books and decorative items. A small white coffee table enhances the cozy atmosphere.

Home in Union Pier

New Pool, Hot Tub, Short Walk To Beach

4.74 out of 5 average rating, 100 reviews

The exterior of a two-story house features a light brown facade with dark red shutters framing the windows. A white front door, accented with a decorative arch, leads to a small staircase. The landscaped yard includes a path and greenery, creating an inviting entrance.

Home in South Bend

Year Round Hot Tub, Outdoor Pool, 3 Bedroom & Bar

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.

An outdoor pool is surrounded by a spacious deck featuring lounge chairs and patio tables. Sunlight reflects off the water's surface, while the area is framed by greenery, creating an inviting space for relaxation.

4.67 out of 5 average rating, 3 reviews

New Buffalo Condo Indoor & Outdoor 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.

A private balcony is featured, furnished with a round table and four black woven chairs. The view showcases the community parking area and marina beyond, framed by the clear sky and trees in the distance.

4.87 out of 5 average rating, 15 reviews

Idyllic New Buffalo Condo: Walk to Beach & Shops!

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!

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.

4.6 out of 5 average rating, 5 reviews

New Buffalo Condo with Association Pool and Beach!

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.

4.94 out of 5 average rating, 93 reviews

Nightingale Dunes - Modern beach town retreat

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

Other vacation rentals with a pool

4.93 out of 5 average rating, 74 reviews

Home in Schererville

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

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

Vacation home in Stevensville

An aerial view captures a lakeside community featuring numerous chalet-style homes. Lush greenery surrounds the area, with the shimmering expanse of Lake Michigan visible in the background. A swimming pool and recreational facilities can be seen, along with parking areas and sandy volleyball courts.

4.93 out of 5 average rating, 69 reviews

A-Frame On Lake Michigan - beach, sports, + pool

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)