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Family-friendly holiday rentals in East Gwillimbury

Find and book unique family-friendly homes on Airbnb

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Popular amenities for East Gwillimbury family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Midtown
4.96 out of 5 average rating, 46 reviews

Great Davenport Hillcrest House

DylanRating, 5 stars5 months ago
Our trip was made better by staying her. The house is beautiful and comfortable and Ottilie wad a courteous and wonderful host. well worth the cost
Home in Windfields
4.44 out of 5 average rating, 9 reviews

Amazing Modern house for all Families near OPG

NathanRating, 5 stars74 months ago
Great place to stay. Excellent communication. Benson always got back to me within 5 minutes of any questions I had. House had everything you need. Already have the house booked again in March.
Home in York
4.89 out of 5 average rating, 75 reviews

Luxury Modern House: Hot Tub, Gym & Steam Shower

ElizabethRating, 5 stars7 months ago
Comfortable and clean in a lovely location. Host was extremely responsive. Highly recommend.
Apartment in Rexdale
4.7 out of 5 average rating, 53 reviews

Mansions of Humberwood

LauraRating, 5 stars3 months ago
Wow! Harjot was an incredible host—kind, caring, and went above and beyond to make our stay as comfortable as possible. The description was spot-on and our experience truly exceeded expectations. This place is a hidden gem in the GTA. The condo offers fantastic amenities, providing plenty of activities when the weather isn't ideal. Highly recommend this space and would definitely book again!
Guest favourite
Apartment in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars1 month ago
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!
Superhost
Cottage in Orillia
4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

AnnalisaRating, 5 stars31 months ago
We spent a couple of days up here, and it was as described. It took me back to my childhood! The classic “by the lake” cottage. And it is that. Complete with a breezeway with life jackets, a great dock, and of course the fantastic lake. We enjoyed a campfire, and the place had everything we needed, for meals and memories. It is a cottage though. You should expect that. It isn’t fancy, and Geoff doesn’t describe it that way. It is how he describes. Geoff is also very responsive, and when we had a question, came back right away. It was a nostalgic little getaway for us! We loved it.
Cabin in Brechin
4.86 out of 5 average rating, 7 reviews

Stunning Waterfront Cottage

StephanieRating, 5 stars7 months ago
Arlee was a sublime host. All of amenities were just as described. the location was great, host was extremely responsive and helpful. I would definitely come back and visit this place again with our family
Guest favourite
Flat in Whitby
4.95 out of 5 average rating, 221 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

BrandonRating, 5 stars1 week ago
Our stay at the Serenity Suite was nothing short of wonderful. Will definitely be looking for availability next time in town!

Family- and pet-friendly home rentals

Guest suite in Ajax
4.62 out of 5 average rating, 206 reviews

Cozy Apt(Walkout Basement) Sleeps 4- 6 & parking

BelindaRating, 5 stars1 month ago
Exactly as described. Nothing fancy. Decent place to sleep, better than a hotel room for the price. Adele was very responsive and communicated regularly. Was a little hard to cook, not a full kitchen but we managed ok. Nice deck to sit on and park across the street. Fairly close to everything, including the lake. Would stay here again. Thanks Adele.
Superhost
Home in Yonge and Eglinton
4.69 out of 5 average rating, 135 reviews

Charming 3 Bedroom & 1.5 bath (Yonge&Eglinton)

KerryRating, 5 stars2 months ago
⭐️⭐️⭐️⭐️⭐️ We had an amazing stay at Julie's place! Julie was instantly responsive and friendly, making us feel right at home. The house is ideally located and super pet-friendly, accommodating our rugged family perfectly. We loved the large dining area, which was fantastic for family meals, and the modern kitchen with a fun Euro stove was a highlight. She had everything we needed, and whenever I reached out, Julie was right there within seconds. I’d give her 10 stars if I could! Highly recommend!
Superhost
Bungalow in Vaughan
4.84 out of 5 average rating, 44 reviews

Spacious, Bright 3 BEDS, 3 BATHS ♥ of Woodbridge

JenniferRating, 5 stars4 months ago
We loved staying at Ann-Marie’s place. It is HUGE! And there are many beds and bathrooms. A great place to gather. We didn’t use the backyard but it looked like fun to sit around the fire pit. Would highly recommend Ann-Marie and her place.
Top guest favourite
Home in Ajax
4.96 out of 5 average rating, 27 reviews

3 bedroom bungalow in South Ajax

AmandaRating, 5 stars2 weeks ago
My family and I stayed at Mrinals unit for 5 weeks during the renovation of our new house. I can say of all the airbnbs I've ever stayed at, this one has been the most stocked, she stocked us with paper towel, toilet paper, laundry detergent, dishwasher detergent, dish soap. Essentially everything you will need to stay comfortably was included! The places also offered us extra linens and the softest and most plush towels. Overall, we had a wonderful 5 week stay, Mrinal was extremely easy to get a hold of and was very flexible for me to extend my stay due to delays. I would 100% recommend this unit to anyone needing to stay in Ajax!
Cottage in Innisfil
4.8 out of 5 average rating, 15 reviews

Art Deco Home near Lake Simcoe W/Patio & Fire pit

SonjaRating, 5 stars20 months ago
Our stay was easy right from the beginning, super flexible as we changed our dates. Instructions were clear and helpful, we also received information about a nearby private beach which was super helpful and timely, we had a lovely walk there in the first night. We loved the house, it is so spacious with everything you could need. There was a lovely outdoor space too. We would highly recommend this house and host! Thank you!
Guest favourite
Home in Richmond Hill
4.89 out of 5 average rating, 149 reviews

Luxury 5 beds, 6 Baths custom home

MosheRating, 5 stars1 month ago
Jay is an exceptional host—always available when needed and incredibly reliable! The place is fantastic, impeccably clean, and feels just like home. Absolutely spotless!
Guest favourite
Guest suite in Toronto
4.89 out of 5 average rating, 229 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

KatherineRating, 5 stars1 week ago
Don & Lucy were great hosts and were super responsive and friendly. We needed a place to stay in our neighbourhood for a week on the fly with our two teenage sons and our dog - their suite fit the bill. Kitchen was loaded which I appreciated making it easy to eat in or walk and grab some local takeout. There was enough room to chill and hang out as well. Loved having an inexpensive lot literally across the street to park in overnight. Would highly recommend!
Home in Oro Medonte
4.95 out of 5 average rating, 102 reviews

Maple Syrup Time in Ski Country

AngelaRating, 5 stars37 months ago
We enjoyed the weekend we spent at Sylvia & Rick Inn and how they did everything possible to make our stay as enjoyable as possible. Good tips for activities as well!

Family-friendly home rentals with a pool

Apartment in North York
5 out of 5 average rating, 11 reviews

Charming One Bedroom Condo

EleftheriaRating, 5 stars1 month ago
Great location, comfortable apartment. Host was very responsive and helpful, Amazing views!
Top guest favourite
Home in Scarborough
4.86 out of 5 average rating, 42 reviews

Fantastic Family Get Away- sleeps 8

HeatherRating, 5 stars7 months ago
Our family of 6 stayed at this wonderful family home for a week. My in laws are in their 70s and our two boys are ages 5 and 8. This home was the perfect layout for all of us. We all had our own space and the boys really enjoyed hanging out in the backyard “gazebo.” Upon arrival, we immediately felt right at home. This place has a beautiful, peaceful feel to it. Everything was clean and well laid out and the hosts have not missed a thing for their guests. Their guidebook was very thorough and helpful to those new to the area of Toronto/Scarborough. We did not have a car but found it very easy (and quick) to get around via Ubers. We were downtown for a blue jays game (kids Jay sundays are great!!) and a concert. We also spent one afternoon at the hockey hall of fame and the St. Lawrence market. A wonderful oasis to come “home” to at the end of a day in the city. The neighbourhood is so lovely just like this home. Thank you Liz and Derek for an amazing holiday!
Superhost
Farm stay in Cannington
4.9 out of 5 average rating, 83 reviews

Hidden Farm Escape in the Heart of the Kawarthas

AmanpreetRating, 5 stars8 months ago
This place was beautiful and homey! Honestly, the upper floor was much bigger than we expected and very clean. The bathrooms were all renovated and looked beautiful. The space was nice and kitchen was very pristine. The pool area was enjoyable and pond was nice to boat in. Would recommend this place for a nice family cottage trip :)
Apartment in Markham
4.77 out of 5 average rating, 181 reviews

LUXURY CLEAN PENTHOUSE AT YONGE AND STEELES

TonyaRating, 5 stars2 months ago
Great host and location. This host is very responsive. The location is large, convenient, and comfortable. We will stay again !
Guest favourite
Home in Uxbridge
4.86 out of 5 average rating, 88 reviews

The Ridge Roost - Uxbridge Township

CarolRating, 5 stars3 months ago
Stephen and Wendy were great hosts. They responded to every question and need and made us feel at home. The stay was quiet and very comfortable. Thank you Stephen and Wendy for accommodating all of our needs. I highly recommend Stephen and Wendy’s Air bnb.
Tiny home in Bradford West Gwillimbury
4.75 out of 5 average rating, 44 reviews

Guest house with electric appliances no oven.

JannaRating, 5 stars1 month ago
I had to travel for my studies and spent 5 days here...it was absolutely perfect for what I needed.... somewhere quiet to study, cozy to sleep, compact convenient kitchen and bathroom. I appreciate the hosts quick responses, and hospitality. The location is excellent, just 15-20 minute drive into Barrie, and very easy to navigate.
Guest favourite
Guest suite in Scarborough
4.89 out of 5 average rating, 93 reviews

Comfortable Suite in the Prestigious Bluffs Area

PrimaRating, 5 stars4 months ago
Harold's place is on a beautiful, private street, where nature sings back to you! Gorgeous nature is around the property. Harold is an amazing host, very kind and helpful in ways that were above and beyond! I would definitely recommend this place as a private and peaceful retreat!

Quick stats about holiday rentals that are family-friendly in East Gwillimbury

  • Total rentals

    90 properties

  • Nightly prices starting at

    £8 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore