Family-friendly holiday rentals in Glenview

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Glenview family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Lake Villa
4.86 out of 5 average rating, 43 reviews

Lakeside Getaway

AndreRating, 5 stars11 months ago
Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!
Guest favourite
Cottage in Antioch
4.93 out of 5 average rating, 149 reviews

#4 Adorable Lake Cottage-Cypress Resort & Marine

JenniferRating, 5 stars10 months ago
This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.
Guest favourite
Home in West Town
4.85 out of 5 average rating, 316 reviews

Lux Urban 3BR/3BA Duplex + Parking!

AllisonRating, 5 stars4 weeks ago
Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.
Superhost
Cottage in Antioch
4.89 out of 5 average rating, 84 reviews

#8 Hillside Cottage at Cypress Resort & Marine

DaveRating, 5 stars3 weeks ago
This was my second time staying at this lakehouse, and it was just as great as I remembered. I absolutely love the peaceful surrounding area—it's a perfect spot to relax and enjoy nature. The hosts were very responsive and helpful, answering any questions I had right away. Everything in the listing was exactly as described, and the check-in instructions were clear and easy to follow. The house was clean, comfortable, and had everything I needed. I’m already looking forward to coming back again!
Superhost
Home in Antioch
4.94 out of 5 average rating, 106 reviews

#1 Old Lake House at Cypress Resort & Marine

NallelyRating, 5 stars8 months ago
Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!
Flat in Bronzeville
4.33 out of 5 average rating, 27 reviews

Spacious 2bdm unit 15min to Dwtn

HeavenaRating, 5 stars1 month ago
i loved this airbnb, great spot if you just want to explore chicago. max was super quick with responses and helpful with any questions i had.
Apartment in Andersonville
4.89 out of 5 average rating, 9 reviews

Bright and Beautiful Penthouse - Close to the lake

GautamRating, 5 stars34 months ago
We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.
Superhost
Home in Bristol
4.84 out of 5 average rating, 109 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

KristyRating, 5 stars4 days ago
Will was very responsive and his place was very relaxing and cozy. My family had a great time!

Family- and pet-friendly home rentals

Guest favourite
Flat in Roscoe Village
4.96 out of 5 average rating, 303 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

LetaRating, 5 stars2 weeks ago
I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.
Guest favourite
Flat in Logan Square
4.9 out of 5 average rating, 405 reviews

Sunny Logan Square Artists' home

KatyRating, 5 stars2 weeks ago
We loved our stay at Kyle’s place - it was decorated SO cute (I went with two girlfriends and I’m pretty sure we all squealed with joy when we first opened the door). The location was perfect - just a quick walk to all the shops and restaurants Logan Square had to offer - and to public transportation (which we used the whole time in Chicago). The neighborhood was very peaceful and quiet; we all felt very safe. When I come back to Chicago, I will absolutely be staying here again. Thanks for sharing your space with us, Kyle! We loved it! (Side note: you gave me so many ideas for house decor, your style is impeccable!)
Top guest favourite
Home in Uptown
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Top guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 294 reviews

Stylish Studio in Historic Logan Square

PeterRating, 5 stars1 week ago
Liz and Martin did a great job providing clear instructions for check in and the place was exactly as described. The room was very clean and provided a lot of privacy. Great location and is convenient to the subway and the area has a lot to do.
Top guest favourite
Guest suite in Portage Park
4.94 out of 5 average rating, 163 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

TerenieRating, 5 stars5 days ago
Jamie was a really amazing host! She was friendly, helpful, caring and went over and beyond to make sure me and my kids were comfortable and had everything we need. Gave us lots of great recommendations to restaurants and as a first timer in Chicago she made sure I was aware of the traffic and other helpful information! My kids LOVE her she was vey nice, patient and gentle with them. Kid friendly house/area VERY quiet. The beds are the BEST after a long day of traveling very comfortable. The place was beautiful very nice decor and nicely maintained. We will definitely be staying here on our next visit to Chicago.
Top guest favourite
Flat in Andersonville
4.93 out of 5 average rating, 436 reviews

Andersonville Living

AndrewRating, 5 stars3 weeks ago
Comfortable, homey place for our group of five. Great back deck for outdoor time. Wonderful neighborhood with lots of shops and restaurants. Good beds.
Top guest favourite
Flat in Logan Square
4.95 out of 5 average rating, 517 reviews

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

NatalieRating, 5 stars2 weeks ago
Great host. Would definitely stay again. Good location, convenient subway within a few minutes walking. 12 min to Downtown.
Guest favourite
Flat in Logan Square
4.96 out of 5 average rating, 122 reviews

Garden Unit Getaway-Bucktown

HaleyRating, 5 stars2 weeks ago
great stay, super clean apartment, great communication on keith’s end would definitely stay again. thank you for accommodating me!

Family-friendly home rentals with a pool

Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars10 months ago
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Flat in The Loop
4.77 out of 5 average rating, 223 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

JaredRating, 5 stars2 weeks ago
The location is perfect for getting to any part of Chicago. It's within walking distance of endless activities, and within one to two blocks of multiple "L" and subway lines that will take you anywhere. You are staying in the middle of the city, so you will hear the train and sirens throughout the night; however, the host provides disposable ear plugs which were very helpful. I had no problem sleeping throughout the night. Front desk staff is always friendly. The host is very responsive, and courteous. Washer and dryer in unit helped me with not having to pack as many cloths for my trip. Everything was spotless upon arrival. Would absolutely stay here again.
Guest suite in Berwyn
4.68 out of 5 average rating, 44 reviews

Music Hot Spot’s Main Level

JamesRating, 5 stars2 months ago
A great stay right near a Main Street. Tons of options for going out but still quiet in your space. Warning. You will smell the BBQ restaurant and you will salivating.
Superhost
Chalet in Ingleside
4.84 out of 5 average rating, 389 reviews

"A" Frame Brandenburg Lake

LisaRating, 5 stars2 weeks ago
Stephen was a great host. The grounds are beautiful! Very peaceful and quiet. The house is nice and cozy. I will definitely stay there again!
Place to stay in Berwyn

Beat-Town Flex Stays

KimberlyRating, 5 stars25 months ago
Second stay. Rose accomplishes blending comfortable clean accommodations with a relaxed and folksy vibe. Recommended!
Flat in The Loop
4.76 out of 5 average rating, 242 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

RobertRating, 5 stars3 weeks ago
Great location and nice floor plan. A bit noisy because of the elevated train, however, earplugs were provided and I enjoyed watching the trains. I would definitely stay there again.

Quick stats about holiday rentals that are family-friendly in Glenview

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹6,044 before taxes and fees

  • Total number of reviews

    440 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore