
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.

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.

The Metropolitan Retreat (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

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.

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

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.

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!

Cozy cottage for two 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.

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.

50th Floor Mag Mile Views, Balcony, Pool, Gym
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.

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 and hot tub. Property on 6 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 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .

Couples, Quiet, Skiing Close, Romantic, Farm, Cozy
Escape to this private, renovated bungalow for two, nestled in nature. Perfect for a quiet retreat, it features a dedicated workspace, fast Wi-Fi a well equipped kitchenette and a seasonal stock tank pool. Enjoy private walking trails on a scenic farm yet you’re only 45 minutes from Notre Dame, Shipshewana, and Lake, Michigan beaches. A charming and peaceful getaway awaits.

The Cranny at Michaels Nook
The Cottage is located in the woods, with a large grass yard featuring a large heated in ground pool and a 6 person Caldera hot tub. Great place for a couples retreat or a small family gathering. Pool is closed for winter from Sept 30th to May 30th. Hot tub is open year round.
Popular amenities for Northwest Indiana rentals with a pool
House rentals with a pool

4 BD Notre Dame | Pool | Hot Tub | Fire Pit | BBQ

Luxury home with pool.

Hot Tub Retreat | Private, Peaceful & Cozy

Just Updated in Lakeside | Pool + Hot Tub + Porch!

Beautiful, sunny 4 BR home with pool and hot tub

Beautiful home in Beachwalk/Notre Dame weekends

Pool House On The Lake

5 Bedroom Luxury Home In Heart of Beachwalk Resort
Condo rentals with a pool

Large 3BR w/ pool and parking - near everything

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Idyllic New Buffalo Condo: Walk to Beach & Shops!

Perfect Location Condo Pools Walk to all Beach 1.5

Nightingale Dunes - Modern beach town retreat

New! Dave's Last Resort Lakeside-Comfy Cabin 5

Sunset Pointe Chalet #31: Beach+ Pool + Games

Flexible & Fresh Lakefront Condo
Other vacation rentals with a pool

Upscale High-Rise Apt · Rooftop Pool + Views

Munster hide away

Hilltop Cove- Beautiful 2 bed/ 2 bath in Beachwalk

Stay Gold, a Sawyer retreat

Enchanting Pool House (2.2 miles from Notre Dame)

Resort Villa with Pool and Hot Tub

Studio unit with kitchenette #2

Andersonville Luxury Pool Escape
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- University of Chicago
- The 606
- Chicago Cultural Center




