Vacation rentals with a pool in Northwest Indiana

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Northwest Indiana

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

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Guest favorite

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.

Guesthouse in Merrillville

4.94 out of 5 average rating, 143 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.

Top guest favorite

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, 109 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.

Superhost

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

4.88 out of 5 average rating, 135 reviews

Experience Fall Beauty & Harbor Country Charm!

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.

Guest favorite

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

4.95 out of 5 average rating, 218 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 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.

Top guest favorite

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

4.96 out of 5 average rating, 184 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.

Top guest favorite

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

4.96 out of 5 average rating, 226 reviews

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!

Guest favorite

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

4.97 out of 5 average rating, 126 reviews

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.

Top guest favorite

A natural pathway leads to a charming safari yurt, adorned with greenery and decorative elements. A wooden archway introduces the entrance, while a nearby barrel sauna complements the serene outdoor setting, surrounded by trees and mulch landscaping.

Yurt in Homewood

4.98 out of 5 average rating, 125 reviews

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN! April - mid Nov RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Gazebo w/2 twin beds (seasonal) Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest Contact me for Fall/Winter Glamping no more than 10. RV and Safari Yurt not included in Winter. Event Yurt is. It's heated!

Guest favorite

The swimming pool area features a vibrant blue pool with a fountain at its center. Surrounding the pool, comfortable loungers are arranged, and hanging flower planters add a touch of greenery. A spacious building is visible in the background, framed by lush trees.

Guesthouse in Porter

4.88 out of 5 average rating, 825 reviews

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Hot tub open all year! Pool will reopen May 1. The Pool Barn is only 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Outside enjoy our Pool, hot tub, grill, firepit, playground, & we are on the hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 5 beds, couch, & full kitchen. No cleaning fee. Book today!

Top guest favorite

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

4.99 out of 5 average rating, 106 reviews

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.

Top guest favorite

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

4.98 out of 5 average rating, 174 reviews

Couples cottage with hot tub!

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.

Guest favorite

A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.

Apartment in Chicago

4.9 out of 5 average rating, 120 reviews

50th Floor Mag Mile Studio

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.