Kid-friendly holiday rentals in Valparaiso

4.9 out of 5 average rating, 364 reviews

Best Deal In Michigan City 1.3 miles to Beach

StevenRating, 5 stars2 months ago

We stayed at Crystal's during the Christmas season and we enjoyed it very much. The house itself was very comfortable and clean. The roominess allowed my family of 6 to spread out and enjoy ourselves. The close proximity to the outlet mall was great! We also visited a local winery (Shady Creek) and had a fantastic time. Crystal's is a definite recommendation.

4.96 out of 5 average rating, 183 reviews

Cottage in New Buffalo

Voted #1 Family Getaway In SW MI for 2019-2024

NicoleRating, 5 stars6 months ago

Great property for two families with small kids! The listing has everything you need, including pack and plays & a highchair. Dana was super responsive and laid out easy instructions + local recommendations. S’mores on our last night was a big hit!

4.88 out of 5 average rating, 104 reviews

Home in Three Oaks

The Lucky Charm House -Walk to it all! Cute, cute

KyungRating, 5 stars5 months ago

Great place to stay with dogs. Very large fenced in yard. If you do have a smaller dog, you need to keep an eye on them because there's gaps at the bottom in some areas that they can squeeze out of. I can confirm with our 10 lbs yorkie who did just that. The yard chairs were a bit scary. They were breaking and felt very unstable to sit in. Central AC was nice and kept the whole house very cool. Having 2 bathrooms is a bonus.

4.92 out of 5 average rating, 130 reviews

Cottage in Stevensville

Escape to The Sunshine Cottage of Harbor Country!

RebeccaRating, 5 stars4 months ago

The home was very easy to find, and was in a little neighborhood. The house was very clean and had a very relaxed atmosphere. Atmosphere Kate was responsive to all of my requests and made it very easy to check in

4.87 out of 5 average rating, 158 reviews

Cottage in Grand Beach

Beachglass -Golf Cart Family Friendly Kids & Pets

LuisRating, 5 stars3 months ago

I really enjoyed my stay. The place was cozy and comfortable. Very clean and matched the description. There was much to do in the area and only about 5 minutes from downtown New Buffalo. Kayse was very helpful and responsive if I had question. I would book again!

4.92 out of 5 average rating, 310 reviews

Home in New Buffalo

New Buffalo / Farmesque with a splash of modern

NoelleRating, 5 stars3 weeks ago

There were 9 of us girls that visited for a lovely winter girls weekend. We had the best time! Plenty of space for all of us to cook, play games, and hang out. Would definitely love to visit in the future again! Highly recommend for walkability and space.

4.94 out of 5 average rating, 108 reviews

Home in New Buffalo

The Riviera Beach Retreat one mile from downtown

VictoriaRating, 5 stars4 months ago

Can't say enough good things about Misty and the house. We did a girls trip and it was perfect. The house is beautiful, the neighborhood is quiet with the beach very close to the house. We loved it so much we talked about when we could come back! Thank you Misty!

Apartment in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

MariaRating, 5 stars6 months ago

We've stayed here before. It's always really clean and nice. The towels are super soft, and the pillows and linens are awesome. You're right across from the outlet mall, and a farmers market type store across the other way. There's a cute little ice cream shop on the corner. You're close to the beach and the zoo. It's just a nice place to rest and reset. I highly recommend it.

Apartment in Lincoln Square

4.96 out of 5 average rating, 361 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

JesseRating, 5 stars3 months ago

I live in the neighborhood and had family visiting for the holidays -- this was a great location, close by to me and easy street parking. My parents enjoyed having space to relax in the morning with their coffee. My teenage niece loved looking through all of the puzzles and games. This is a great space for anyone coming to the city to explore - a quiet street yet easy to access everything in Lincoln Square and the rest of the city via bus or train. Highly recommend, a great space for any group.

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Popular amenities for Valparaiso kid-friendly rentals

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Free parking on premises

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Child-friendly house rentals

4.83 out of 5 average rating, 241 reviews

Home in Cedar Lake

Vacation home on south end of Cedar Lake

ToddRating, 5 stars1 week ago

What a great place. Close to everything. Loved it.

4.92 out of 5 average rating, 106 reviews

Beautiful home with Beach views in Beachwalk

SamanthaRating, 5 stars4 months ago

Well-maintained house, spotless upon arrival, great view of the area from the kitchen. Ice machine was a great touch especially with a bunch of people in the house! Would definitely come back!

4.94 out of 5 average rating, 157 reviews

Home in Sawyer

Beautifully eclectic Sawyer cottage

ReneeRating, 5 stars2 months ago

Really enjoyed Tim's place. It was very spacious and clean and the space had a great vibe. It was centrally located to a lot of restaurants and places and the hot tub was huge. Nice quiet location. Would definitely stay here again.

4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

KarynRating, 5 stars2 months ago

Very spacious and just as described. Perfect location for visiting family and would be great in the summer!

4.95 out of 5 average rating, 63 reviews

Home near the lake with an inground pool

FreddieRating, 5 stars2 weeks ago

Clean house and will definitely book again for our needs. Very comfortable with everything.

4.96 out of 5 average rating, 165 reviews

Home in Momence

Riverfront Oasis: Parks+ Kayaks+Relaxation Await!

MonicaRating, 5 stars3 weeks ago

Enjoyed the home..enough room for whole family

4.91 out of 5 average rating, 145 reviews

Pet Friendly Getaway with Hot Tub!

EmmyRating, 5 stars1 week ago

The house was very cute and exactly what we were looking for! A great cozy weekend away.

4.95 out of 5 average rating, 245 reviews

Cozy House near Beach, Casino, Outlets, & Hiking

CraigRating, 5 stars6 months ago

Cozy place, friendly hosts, great communication, exactly as described.

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Kid-Friendly apartment rentals

Apartment in Lincoln Park

4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars2 months ago

We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

Apartment in Lincoln Square

4.79 out of 5 average rating, 289 reviews

Cozy Garden-Subterranean Apartment

BenRating, 5 stars2 months ago

Great place and neighborhood. The place was definitely cozy and matched exactly what the listing described.

Apartment in Lincoln Park

4.82 out of 5 average rating, 282 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

KirbyRating, 5 stars1 month ago

Excellent 2 bedroom in Lincoln Park. Architecture is wonderful, the amenities were all as described, and the host was proactive about an issue we had with the heat. Would definitely book again!

4.85 out of 5 average rating, 117 reviews

Apartment in Hyde Park

Garden Apartment in captivating Hyde Park

GregRating, 5 stars1 month ago

I had a really nice stay at Jon’s place. Very big space and well kept. Great hosts. Good location in Hyde Park near 53rd street restaurants and shops and the Whole Foods on Hyde Park Blvd

4.84 out of 5 average rating, 245 reviews

Apartment in Evanston

Adorable 1BR apartment near Northwestern

BeckyRating, 5 stars1 month ago

This was a great home base for a weekend of activities in the north suburbs! The kitchen had been recently updated and there were nice homey touches throughout - extra blankets, coffee maker, etc. I might have to return in the summer just for the adorable backyard space!

4.82 out of 5 average rating, 173 reviews

Apartment in Evanston

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

RobertRating, 5 stars1 week ago

We have stayed here numerous times, have always been completely satisfied with our accommodations, and intend on returning really soon!

Apartment in Logan Square

4.88 out of 5 average rating, 120 reviews

Bright, Cheery Logan Square Getaway

MelissaRating, 5 stars3 months ago

Great location! The place was very easy to find and within walking distance some really good restaurants. Loved our stay!

Apartment in Logan Square

4.95 out of 5 average rating, 504 reviews

2nd floor of 1908 brick two-flat in Logan Square

GinaRating, 5 stars6 days ago

I stayed for about a week at Paul and Sarah's home and it was very pleasant. They provided very detailed instructions for check-in and I had no problems navigating to the building. The apartment itself is cozy and gets plenty of light in the daytime, though the floorboards were a bit creaky so I recommend treading lightly if you're someone with heavy footsteps. The TV also doesn't come with a streaming device so if you plan on watching Netflix/etc. be sure to bring your own device or an HDMI cable that can mirror a laptop. There was also an induction plate provided for light cooking which was helpful on the days I didn't want to do takeout. Overall this was a great home base for exploring Logan Square with very easy access to other neighborhoods/downtown via the Blue line and bus.

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Child-Friendly Holiday Condos

4.81 out of 5 average rating, 115 reviews

Condo in Evergreen Park

Evergreen Park Condo with balcony and Jacuzzi tub

KindallRating, 5 stars2 months ago

The stay was nice and clean and very convenient location.

4.95 out of 5 average rating, 122 reviews

Condo in Bridgeport

Entire 3Bed/2Bath Condo Near McCormick & Metro

VeraRating, 5 stars2 months ago

Super apartment, very clean, bathroom good. Everything, especially kitchen, well equipped. John always responded immediately and guided you how to get in the apartment. 100% recommended

4.9 out of 5 average rating, 108 reviews

Condo in Bridgeport

Convenient & Spacious 3BR Condo w/Free Parking

DanRating, 5 stars1 week ago

Great place in a quite neighborhood. Close to the convention center and really close to some awesome restaurants.

4.82 out of 5 average rating, 339 reviews

Condo in Wrigleyville

Dream Condo steps from Wrigley Field!

CarrieRating, 5 stars3 months ago

I’ve stayed at one of his places before and both times super clean, easy to get to. Josh was always so quick to reply. Bonus was it included parking! Will stay with him again

4.98 out of 5 average rating, 127 reviews

Condo in River North

Luxurious River North 3BR/2BA- Free Onsite Parking

DaraRating, 5 stars2 months ago

This place was great and very accommodating for our for our family of 6 (parents & 4 young adult kids). We were able to walk everywhere. Hosts were very communicative and very responsive. And, what a surprise to wake up to a delivery of Stan's Donuts!!! Definitely would recommend this place to anyone visiting Chicago.

4.92 out of 5 average rating, 118 reviews

Condo in Chinatown

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown

SunoakRating, 5 stars4 months ago

This location was perfect for our weekend trip. It was located right by the subway station and easily accessible by car. The space was clean and there were plenty of towels and the kitchen was stocked. We were there for the Chicago Marathon and the route went right through Chinatown. There is parking available on the street in front of the listing but there is also a public parking lot a couple blocks away.

4.83 out of 5 average rating, 135 reviews

Condo in Pullman

Gamers Getaway 20 minutes from downtown

Jakalia LRating, 5 stars5 months ago

The Airbnb was amazing, I had a few friends stay with me we had a nice time the host is very helpful and nice always responding fast if I needed anything . Overall stay was great.