Holiday rentals with a pool in Northwest Indiana

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.

Value · Location · Condition

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.

Value · Location · Cleanliness

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)!

Location · Family · Access

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.

Location · Value · Layout

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.

Location · Value · Amenities

Fun game-room suite with hot tub & optional Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest

Location · Value · Hot tub

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.

Value · Location · Walkability

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.

Value · Location · Beach

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

Family · Location · Air conditioning

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) .

Location · Family · TV

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Just a few days left this summer at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection to loved ones and nature + 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.

Family · Location · Accuracy

Studio apartment for two with pool & 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.

Location · Family · Wi-Fi