Family-friendly vacation rentals in Gary
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Top-rated family-friendly rentals in Gary
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Gary family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Bridgman
4.79 out of 5 average rating, 103 reviewsRelax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours
Clean and comfortable home for our family get away!
Townhouse in New Buffalo
4.93 out of 5 average rating, 102 reviewsDunescape Beach Retreat, Downtown New Buffalo
Had a wonderful stay at the Townehouse in New Buffalo. Beautiful home. Loved all the outdoor patios and enclosed seating area. Spacious rooms and fully stocked bedding and linens. Perfect location right downtown. Walking distance to beach and shops and restaurants. Couldn’t ask for a better spot. Mark was very friendly and accommodating. Can’t wait to go back.
Home in Three Oaks
4.97 out of 5 average rating, 172 reviewsThe Getaway - Three Oaks - 3 BR 1.5 Bath
Lovely place, very clean, great for families or groups with multiple bedrooms. Very clear instructions from the hosts and easy to check-in and out. We stayed here for Notre Dame football game, and it was easy 35 minute drive to South Bend with no traffic; also easy to exit after the game because no traffic at all in our direction. Cute little town a few blocks away with some local shops and restaurants.
Cottage in Union Pier
4.95 out of 5 average rating, 299 reviewsJ’s Beach House: Hot Tub & short walk to beach!
Jen was so sweet, messaged back right away and gave us a list of things to do while we were there on a mini vacation visiting family. Hot tub and deck so clean, amazing and private Thank you and Happy holidays.
Cottage in Three Oaks
4.87 out of 5 average rating, 185 reviewsBlueberry Fields/ House and Retreat
My fiancé and I visited Donna’s place over a summer weekend, and we had the most amazing time. Donna’s house is so beautiful and welcoming - we felt at home. Her place was clean and is filled with the most thoughtful decor. It has everything anyone needs for a peaceful, relaxing stay. She was responsive right from the day of booking to our final day and even stopped by to meet us in person. We look forward to staying at her house again soon!
Cottage in Union Pier
4.96 out of 5 average rating, 192 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Second time staying in this home and it was even better than the last. Great neighborhood and layout and they’ve made some really nice cosmetic updates to the house as well. Can’t wait to come back in the summer!
Cottage in Valparaiso
4.93 out of 5 average rating, 405 reviewsThe Lake Escape -Cozy Lakefront Cottage Valparaiso
It was our best vacation and meeting the new year. Kim is great and so is her house. We liked everything very much. We will definitely come back in the summer to swim in the lake. Thank you very much for the great service and the wonderful house.
Cottage in New Buffalo
4.94 out of 5 average rating, 161 reviewsPerfect Get Away - Private Hot Tub - Lots of Room
Beautiful home, well stocked with helpful kitchen items, towels, etc. great location and an easy walk to all the shops, restaurants and bars in New Buffalo.
Family- and pet-friendly home rentals
Home in New Buffalo
4.95 out of 5 average rating, 230 reviewsAnna's Cottage
We've stayed at Rob's house before and we've always had a wonderful time. The house is cozy and clean, the furniture is comfortable, and we enjoy the fenced in yard. It's a short walk into town. Rob's house is fun even in the winter.
Apartment in Logan Square
4.9 out of 5 average rating, 388 reviewsSunny Logan Square Artists' home
Great apartment, very clean and well kept, we really enjoyed our stay!
Home in Michigan City
4.86 out of 5 average rating, 117 reviewsLakeshore Manor
Very nice Victorian home. Great location
Guesthouse in Stevensville
4.98 out of 5 average rating, 306 reviewsRed Barn Lodge
We had a great winter weekend at Ann & Tim’s place. The house was very cosy, especially with fireplace going. We enjoyed exploring the nooks and crannies and many books. Ann left us homemade bread and an amazing chocolate stout cake. Delicious! Ann and Tim were delightful hosts and we will be back!
Guest suite in Portage Park
4.95 out of 5 average rating, 151 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Jamie was an amazing host and the stay far exceeded expectations! From the detailed information about the city to the decor in the apartment, it was a stay to remember! Jamie was warm and accommodating as was the neighborhood and apartment! I hope to make this a yearly trip and stay here, with Jamie as my host I would always have a great time!
Townhouse in Old Town
4.85 out of 5 average rating, 164 reviewsDowntown Elegance ✨ Private Yard Parking
Great place! Plenty of beds and bathrooms! The garage was a little tight but street parking was easy. Thanks for everything!
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 329 reviewsa SIMPLE place
What a perfect place to spend the weekend with my mom and daughter. Steve was very friendly and responsive. The house is very nice and clean. It was a perfect fit for us.
Guesthouse in Plymouth
4.99 out of 5 average rating, 567 reviewsSue's Place
Sue's place was just lovely. From the moment when we discovered the homemade muffins waiting for us on the counter, I knew it was going to be a nice experience. I've stayed in a fair number of airbnbs, but this one has to be the cleanest, most comfortable and most carefully - and thoughtfully - stocked, ever. The beds are the most comfortable I've ever slept in - including my own at home! And if you've forgotten to bring/pack anything, I almost guarantee that Sue has it in the cottage. And the fact that we were able to bring our two precious dogs was such a blessing. located just a stone's throw from a lovely, quiet lake, the neighborhood is peaceful and secluded - yeah there are several nice restaurants within a short 10 to 12 minute drive. (The lakeside Puerta Vallarta Mexican restaurant, 5 min away, was some of the best Mexican food I've had in 20 years, BTW...). And there's lots of fun antique stores, coffee shops and restaurants in the town of Plymouth, just 10 min away. Enjoy!
Family-friendly home rentals with a pool
Cottage in Lakeside
4.62 out of 5 average rating, 74 reviewsCozy Cottage Steps to Beach, Pool, Hot Tub & More
Booked the A unit with friends for a wedding hosted at Lakeside Inn .02 miles away.. The kitchen was great, furniture comfy. Steep stairs so may be hard for older folks, but there are two bedrooms on 1st floor. We did not use the hot tub or pool, so no comments. Loved the front room and screened in porch. Lots of options to sit, visit, play games. Nice to be able to seat 10 at the dining room table. We had the property to ourselves, there is a B side, so no issues with neighbors. Shared some feedback with Frank and he appreciated it. If you have a big group—you would love being side-by-side. The unit was great with two nice bathrooms to get ready for wedding! Thanks Frank!
Home in Union Pier
4.89 out of 5 average rating, 27 reviewsUnion Pier Pool home
Awesome stay! Booked here for a nice relaxing weekend get away where we wouldn’t need to travel to have fun. That is exactly what this place offered. Great pool & hot tub, and house has plenty of room making it feel relaxing and gives everyone plenty of space. Easy walk down to the beach - you get to leverage the private side of the beach which is very very nice. Overall great stay and will look to book again!
Tiny home in Sawyer
4.77 out of 5 average rating, 137 reviewsAfter Dune Delight
Such a cute home. Right across the road from the Warren dunes. Easy to get back and forth with a bicycle. The cutest little ice cream shop right next door. Bed was comfortable and the bunk beds are roomy. Would definitely stay here again.
Home in New Buffalo
4.97 out of 5 average rating, 76 reviewsModern Farmhouse - Walk to Downtown, beach & pool!
The Modern Farmhouse was exactly as described and fit 8 adults without any problems. Geoff and Sarah have everything you need in the house. Plus it is a very short walk to great restaurants, the beach, and other things to do in downtown New Buffalo. Most importantly, Geoff and Sarah are very responsive and helpful hosts. I cannot say enough how great they were! They provided us with a wealth of information within their welcome packet, too. I would highly recommend the Modern Farmhouse to anyone wanting to stay in New Buffalo.
Home in Union Pier
4.97 out of 5 average rating, 32 reviews2025 Open! Private Heated Pool and Hot Tub!
Beautiful home! Easy walk to the beach or stay back and enjoy the pool and hot tub! Spacious backyard and plenty to do for everyone! Everything was clean, very clear directions on how everything worked and even provided some recommendations for things to do nearby. Thanks for the hospitality!
Condo in New Buffalo
4.92 out of 5 average rating, 75 reviewsNightingale Dunes - Modern beach town retreat
Joel and Kathi's place is beautiful and very spacious. Kitchen is well-stocked. Lots of sleeping options. Be cautious if you have mobility differences as the only way to the second floor is the spiral staircase. However, all amenities (bedroom, bathroom, kitchen) are available on the first floor. Would love to come back!
Apartment in New Buffalo
4.88 out of 5 average rating, 60 reviewsExit 1 - Escape To The Lake
Beautiful condo in a fantastic location. Great sunsets from the balcony. Would absolutely stay here again.
Home in Mishawaka
4.68 out of 5 average rating, 178 reviewsSleeps 18 w/ Indoor Court, Heated Pool & Hot Tub!
We had 11 adults and five small children in the house for 4 days. There was room to gather and to get away from each other as needed. The indoor pool and hot tub were in great shape and perfect for our family. All appliances worked well. Bathrooms were well equipped. Beds were very comfortable. The host was available when we had questions. Wi-Fi worked great for streaming on multiple devices at the same time. Could use a few more chairs in the dining area.
Quick stats about vacation rentals that are family-friendly in Gary
Total rentals
140 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
4.6K reviews
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
140 properties include access to wifi
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