Family-friendly vacation rentals in Glenview

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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 stars9 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, 150 reviews

#4 Adorable Lake Cottage-Cypress Resort & Marine

JenniferRating, 5 stars8 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, 314 reviews

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars2 weeks ago
Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.
Superhost
Cottage in Antioch
4.89 out of 5 average rating, 82 reviews

#8 Hillside Cottage at Cypress Resort & Marine

JenniferRating, 5 stars9 months ago
Every year we visit Cypress there are more improves and amenities. Always a great stay and so much to do. Amanda and her team run this place like a well oiled machine. We visit once in the winter and once or twice in the summer. A favorite for sure.
Superhost
Home in Antioch
4.94 out of 5 average rating, 106 reviews

#1 Old Lake House at Cypress Resort & Marine

NallelyRating, 5 stars6 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!
Superhost
Home in Bristol
4.83 out of 5 average rating, 103 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

RogerRating, 5 stars6 months ago
Great host. Really looked after us and communicated very well.
Guest favourite
Home in Richmond
4.93 out of 5 average rating, 156 reviews

"About Time" You will love it! -12 beds

SteveRating, 5 stars4 months ago
Very nice place to host our large family Christmas gathering. Plenty of room for everybody. The game room was very much appreciated and well used.
Guest favourite
Guest suite in Antioch
4.96 out of 5 average rating, 83 reviews

#10 Lakeview Apartment at Cypress Resort & Marine

SophiaRating, 5 stars5 months ago
We had such a lovely stay! It felt like a home and was very cozy she even left fuzzy robes on the bed that added to the cozy fall vibes! The hot tub was clean and private and the unit had a beautiful view! Everything together made for the perfect relaxing get away!

Family- and pet-friendly home rentals

Guest favourite
Apartment in Logan Square
4.89 out of 5 average rating, 398 reviews

Sunny Logan Square Artists' home

JordenRating, 5 stars2 weeks ago
Loved our stay. Cool neighborhood with lots to do in the direct area. Great advice from Kyle about where to go. Would definitely stay again!
Guest favourite
Guest suite in Portage Park
4.94 out of 5 average rating, 157 reviews

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

JulieRating, 5 stars2 weeks ago
Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!
Guest favourite
Townhouse in Old Town
4.85 out of 5 average rating, 169 reviews

Downtown Elegance ✨ Private Yard Parking

JohnRating, 5 stars5 days ago
Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!
Top guest favourite
Apartment in Andersonville
4.93 out of 5 average rating, 429 reviews

Andersonville Living

ChristyRating, 5 stars2 weeks ago
We 3 loved our stay at Joseph and William's place! The apartment was clean, bright, and filled with art. The kitchen was lovely, the beds were all comfortable and the shower was very hot. We loved the back deck, and I imagine it gets used so much in warmer weather. The location is perfect. We walked to restaurants and shops in Andersonville. It was just minutes from Loyola Univ. which is why we were in town.
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 337 reviews

a SIMPLE place

KaitlinRating, 5 stars5 days ago
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!
Guest favourite
Apartment in Irving Park
4.94 out of 5 average rating, 237 reviews

Cool and Modern Chicago Apartment near Transit

AlexanderRating, 5 stars2 weeks ago
Definitely a great weekend! The look, and feel of the place was very comforting, and had a great flow. Design was tasteful, and anything that was needed was right where you’d expect it to be! A definite recommend!
Top guest favourite
Apartment in Logan Square
4.95 out of 5 average rating, 509 reviews

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

KathlynRating, 5 stars1 week ago
Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again
Guest favourite
Apartment in Evanston
4.9 out of 5 average rating, 152 reviews

Clean and Bright Stay 2BRM close NU campus

SummerRating, 5 stars5 months ago
Tracy's home is clean, comfortable, and feels like a great home to return to when you are visiting Evanston. we didn't get a chance to cook in their fabulous kitchen, but I plan to next time!!

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 stars8 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!
Apartment in The Loop
4.63 out of 5 average rating, 60 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

ParitoshRating, 5 stars4 months ago
I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!
Apartment in The Loop
4.76 out of 5 average rating, 216 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

LauraRating, 5 stars1 week ago
Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.
Guest suite in Berwyn
4.67 out of 5 average rating, 43 reviews

Music Hot Spot’s Main Level

JamesRating, 5 stars3 weeks 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, 387 reviews

"A" Frame Brandenburg Lake

JoelRating, 5 stars2 months ago
Stephen was a welcoming host and the cabin was exactly as described. The location is secluded and quiet, but you’re also close to groceries, restaurants and fun antique stores. Kitchen is well stocked for cooking meals, and the fireplace is cozy and perfect for relaxing. Even with snow on the ground we enjoyed strolling around the property down to the lake. A wonderful stay, we’d love to visit again.
Apartment in The Loop
4.78 out of 5 average rating, 236 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

SantiagoRating, 5 stars1 week ago
The place is unbelievably well located! One block away from the Chicago Riverwalk and one block from the world famous Michigan Av. You can walk anywhere from here, including Lincoln park, the Hancock tower, Willis tower and the millennium park. Awesome place. It is noisy though! But that’s the price you pay for being right in the center of the action! The place is lovely, comfortable and very nicely furnished!

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    $97 CAD 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