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Holiday rentals with a pool in Michigan City

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Quick stats about holiday rentals with a pool in Michigan City

  • Total holiday rentals

    Explore 150 holiday rentals in Michigan City

  • Nightly prices starting at

    Michigan City holiday rentals start at $339 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Michigan City holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Michigan City rentals

  • 4.8 Average rating

    Michigan City stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Michigan City

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

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Top Guest favourite
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!

4.97 out of 5 average rating, 106 reviews
Top Guest favourite
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, private resort-style neighborhood pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax & 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, 248 reviews
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 Miller

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.

4.97 out of 5 average rating, 128 reviews
Top Guest favourite
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

5.0 out of 5 average rating, 216 reviews
Top Guest favourite
The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.
Home in St. Joseph

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

5.0 out of 5 average rating, 114 reviews
Guest favourite
Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

Atomic Acres is a remodeled, 4 bedroom/3,000 sq ft home in the heart of Harbor Country in Sawyer, MI. This home sits on 5 beautiful acres with a fenced in side yard and open back yard with a wandering creek along its border. The amenities are endless: fire pit, seasonal pool & hot tub, patio, ping pong table, pool table, screen porch and more! An aesthetic nod to the mid century era is felt throughout with pieces curated to appeal to the vintage, and all so close to Warren Dunes (1 mile)!

4.96 out of 5 average rating, 102 reviews
Guest favourite
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.

4.96 out of 5 average rating, 203 reviews
Top Guest favourite
Home in New Buffalo

NB Getaway with HotTub, Pool & 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, 112 reviews
Guest favourite
An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.
Home in Lakeside

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). The pool will close Sept 16th, 2027 this year! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), new hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

4.96 out of 5 average rating, 101 reviews
Guest favourite
Home in New Buffalo

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 10/ 20 and hot tub open year round maintained at 104 f . Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

4.94 out of 5 average rating, 142 reviews
Guest favourite
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.
Guesthouse in Michigan City

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.

4.86 out of 5 average rating, 179 reviews
Guest favourite
A spacious deck surrounds a hot tub, with comfortable loungers positioned nearby. In the background, lush greenery frames an open field, and a wooden bridge spans a small area, enhancing the natural setting of the property.
Home in Berrien Springs

18-acre pond retreat | Heated pool & hot tub

Pool mornings, pond paddles and hot-tub nights come together on 18 private acres. Swim in the seasonal host-heated pool, explore the natural pond by kayak, or move indoors for arcade-style games and time around two fireplaces. Sleeps 16 (10 adults max) across five bedrooms with 3.5 bathrooms, Gigabit internet, a playground and two kayaks with life vests. Pool heat is included May 1–October 1.

4.94 out of 5 average rating, 168 reviews

Popular amenities for Michigan City rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A serene pool area features a heated in-ground pool surrounded by lush greenery. Lounge chairs with red umbrellas provide shaded seating. Colorful flowers and tropical plants enhance the peaceful outdoor setting, creating an inviting place for relaxation.
Home in Miller

Bayless Dune Lodge at West Beach - Indiana Dunes!

4.94 out of 5 average rating, 157 reviews
Superhost
A private pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The area is enclosed by a wooden fence, offering privacy, and a storage shed is visible in the background, complemented by a lush green landscape.
Home in New Buffalo

Secluded Pool Playhouse: Hot Tub, Game Room, Fire

4.83 out of 5 average rating, 102 reviews
Top Guest favourite
A charming cottage exterior is shown with large windows allowing ample natural light. Lush landscaping surrounds the entrance, featuring ornamental grasses and rocky accents. The inviting covered porch provides a welcoming entry point to the home.
Home in New Buffalo

Modern Farmhouse - Walk to Downtown, beach & pool!

4.96 out of 5 average rating, 107 reviews
Guest favourite
A backyard oasis is showcased at dusk, with a heated pool reflecting warm lights strung overhead. Colorful pool floats gently rest on the water's surface, while a fire pit table is positioned nearby surrounded by Adirondack chairs, enhancing the inviting atmosphere.
Home in South Bend

Pool | Hot Tub | Backyard Oasis | Game Room | Fun

4.92 out of 5 average rating, 351 reviews
Guest favourite
A screened-in porch features comfortable seating facing the tranquil waters of Lake Kai. Large windows provide an unobstructed view of the serene sunset reflecting on the lake, creating a peaceful and inviting space.
Home in Michigan City

Beachwalk Home on Lake Kia - W/ Cart Rental Option

4.85 out of 5 average rating, 95 reviews
Top Guest favourite
The exterior of a two-story red house is showcased, featuring a welcoming porch with railings. Large windows allow natural light to fill the home, and a paved pathway leads up to the entrance. Surrounding trees enhance the setting's natural charm.
Home in Michigan City

Beachwalk Resort Stunning 4-Bed + Loft - Sleeps 18

4.99 out of 5 average rating, 91 reviews
Top Guest favourite
Home in Michigan City

6BR BeachWalk Gem | Beach+Pool+Lake Michigan View

4.99 out of 5 average rating, 92 reviews
Guest favourite
Home in Union Pier

Harbor Country Poolside

5.0 out of 5 average rating, 19 reviews

Condo rentals with a pool

Guest favourite
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

4.93 out of 5 average rating, 105 reviews
Superhost
A dining area features a wooden table surrounded by six chairs, creating a space for gathering. A spiral staircase leads to an upper level, while nautical-themed decor adorns the walls. An adjacent open doorway reveals additional kitchen space, enhancing the home's inviting layout.
Condo in New Buffalo

New Buffalo Getaway Condo

4.9 out of 5 average rating, 100 reviews
Guest favourite
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

Perfect Location Condo Pools Walk to all Beach 1.5

5.0 out of 5 average rating, 7 reviews
Guest favourite
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

5.0 out of 5 average rating, 71 reviews
Guest favourite
A spacious sun deck is presented, featuring several lounge chairs and a table under a red umbrella. The deck is surrounded by a wooden railing, with an expansive view of the nearby harbor and distant buildings.
Condo in New Buffalo

(3 Nt Min!) New Buffalo Condo With Association

4.84 out of 5 average rating, 32 reviews
Guest favourite
A spacious living area is brightened by natural light from large windows. A cozy seating arrangement features striped sofas around a coffee table, with a fireplace nearby. The open layout provides a view towards the kitchen and dining area, enhancing the communal feel of the space.
Condo in New Buffalo

Charming New Buffalo Condo: Walk to Lake Michigan!

4.91 out of 5 average rating, 22 reviews
Condo in New Buffalo

Large 3BR w/ pool and parking - near everything

4.92 out of 5 average rating, 72 reviews
Superhost
A shared heated pool is featured in an outdoor area, surrounded by lounge chairs and greenery. A covered patio with seating is visible in the background, along with trees providing shade. Umbrellas offer additional sun protection over certain seating areas.
Condo in Union Pier

Union Pier Condo Close To Everything!

4.75 out of 5 average rating, 4 reviews

Other holiday rentals with a pool

Guest favourite
The two-story cottage features a dark blue exterior accentuated by a prominent white star and porch. The front steps lead up to a welcoming entrance door framed in soft pink. Large windows allow natural light to fill the space, surrounded by lush green trees.
Cottage in Michigan City

Beachwalk’s Cozy Cottage - Farmhouse decor

4.93 out of 5 average rating, 83 reviews
Top Guest favourite
A vibrant yellow front door is complemented by stone exterior and a decorative statue. The private pool area features clear blue water, surrounded by loungers on a spacious deck. An indoor sitting area is arranged with green and yellow decor, large windows allow natural light to fill the space.
Home in Michigan City

Cozy~Well-Curated Home•Private Pool• Dog-friendly!

4.92 out of 5 average rating, 62 reviews
Top Guest favourite
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.

5.0 out of 5 average rating, 61 reviews
Guest favourite
A spacious patio area is visible, featuring a circular in-ground pool surrounded by a sunlit deck. Several white lounge chairs are positioned nearby, along with an umbrella-topped table. A two-story white cottage stands in the background, with large windows allowing natural light to enter.
Cottage in Grand Beach

Cottage steps from Lake Michigan

4.68 out of 5 average rating, 22 reviews
Guest favourite
The charming exterior of a light purple house features a welcoming porch with steps leading up. Large windows allow plenty of natural light, while a white picket fence surrounds the property, enhancing its inviting appeal.
Home in Long Beach

Beachwalk- New Kids on the Beach

5.0 out of 5 average rating, 33 reviews
Top Guest favourite
A charming house is showcased with a striking orange exterior. The covered front porch features white railings and a decorative ceiling. A well-maintained walkway leads to the entrance, bordered by colorful foliage. Nearby homes are visible, set in a peaceful neighborhood with a wooded backdrop.
Home in New Buffalo

Modern 5-Bedroom New Buffalo Lakeside Escape

4.98 out of 5 average rating, 41 reviews
Top Guest favourite
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

4.98 out of 5 average rating, 52 reviews
Top Guest favourite
Home in Union Pier

Perfect Family Getaway!

4.99 out of 5 average rating, 72 reviews

When is the best time to visit Michigan City?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$611 NZD$551 NZD$570 NZD$662 NZD$870 NZD$1,162 NZD$1,264 NZD$1,266 NZD$775 NZD$677 NZD$594 NZD$672 NZD
Avg. temp-4°C-3°C3°C9°C15°C20°C22°C22°C18°C11°C4°C-1°C

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