Holiday rentals with a pool in Michigan City

Guest house in Merrillville

4.92 out of 5 average rating, 188 reviews

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples 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.

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.

4.91 out of 5 average rating, 56 reviews

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

Welcome to The Keystone Ranch! Vintage charm meets modern comfort in our bright & airy, limestone ranch home. It’s a perfect getaway for families or friends…just minutes away from our beautiful beaches & outdoor adventures. We’re located in the ❤️ of Michigan City, close to great food & SO MANY local favorites! What You’ll love… •in ground pool + fenced in yard •3 season lanai + fire pit •Spacious kitchen •Lower level chill space Perfect central location… close to INDIANA DUNES NATIONAL PARK!

4.97 out of 5 average rating, 125 reviews

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.

A charming two-story cottage is showcased, featuring multiple large windows that allow abundant natural light. The exterior is accented by a mix of dark brown and light beige siding, with a wooden door leading into the home. Lush greenery surrounds the property.

5 out of 5 average rating, 14 reviews

Hilltop Cove- Beautiful 2 bed/ 2 bath in Beachwalk

Welcome to Hilltop Cove! Your perfect getaway at our stunning 2-bedroom, 2 full bathroom cottage in the desirable Beachwalk resort community. Nestled just a short walk or golf cart ride away from the incredible amenities this vibrant community has to offer such as a pool, lake and park. Our property promises a relaxing and fun-filled stay for all guests. Book your stay at our Beachwalk spot and experience the ultimate in comfort, convenience, and coastal charm. We look forward to hosting you!

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.

4.85 out of 5 average rating, 94 reviews

Beachwalk Home on Lake Kia - W/ Cart Rental Option

Our Lakehouse is unique in that it's sits directly on Lake Kai - Beachwalk's beautiful interior Lake. Of the 200+ homes located in "Beach Walk" Resort, less than 20 are on Lake Kai making our home very unique & your vacation memorable. It’s definitely one of the most sought out locations in all of Beachwalk ** Exciting NEW Update for the 2026 Season New Golf Cart Rental Option - reserve after booking ** Minimum 30 years of age to book ** ** Maximum capacity is 8 Adults and 8 Children **

4.99 out of 5 average rating, 90 reviews

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

Beach + Resort Amenities! Perfect for families—close to events, water, and summer + fall fun. Located in BeachWalk Community this space offers stunning Lake Michigan views, easy across the street access to the beach, 6 bedrooms, 5 baths, 2 living spaces. This comfortable + relaxing beach setting will sleep up to 18 adults. 3 large decks, grill and outdoor seating. Plus Enjoy access to community pool, pickle ball, paddle boards, coffee/ice cream shop kayaks, playground and other fun rec!

Superhost

A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.

Home in Three Oaks

4.84 out of 5 average rating, 108 reviews

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

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.

4.96 out of 5 average rating, 198 reviews

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.

4.97 out of 5 average rating, 243 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, 134 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.

Guest house in Valparaiso

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.

4.95 out of 5 average rating, 225 reviews

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 optional . 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 after payment of grounds fees.