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, 47 reviews

Great Davenport Hillcrest House

EllenRating, 5 stars1 week ago
Ottilie was an excellent host, and welcomed my group with a beautiful fresh fruit Platter. Such a lovely touch. Ottilie was responsive and helpful and we found her place to be just right for our six day stay.
Home in Windfields
4.44 out of 5 average rating, 9 reviews

Amazing Modern house for all Families near OPG

NathanRating, 5 stars75 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!
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.
Guest favourite
Cottage in Orillia
4.83 out of 5 average rating, 30 reviews

Orkney Beach 1 on the shores of Lake Simcoe

KaylaRating, 5 stars6 months ago
We had an awesome stay. It was girls/moms weekend away. Got to sleep in each morning on comfy beds as late as we wanted but seeing the sunrises was great too! All the furniture was super comfy. The cottage had all the amenities we needed and more. The lake was picturesque and the grounds were beautiful. The hot was the icing on the cake for us ladies though. Clean and the perfect temperature. I would absolutely recommend staying At Orkney Beach and would love to come back again in the summer for a longer stay. 3 night wasn't enough. Murray was a pleasure to deal with. Thanks so much for hosting us!!
Cabin in Brechin
4.86 out of 5 average rating, 7 reviews

Stunning Waterfront Cottage

StephanieRating, 5 stars8 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
Superhost
Cottage in Orillia
4.73 out of 5 average rating, 209 reviews

Waterside Haven: spacious retreat w/hot tub

SidneyRating, 5 stars1 week ago
Brandy was a great host. We stayed for about 5 weeks while our home was being repaired and the house had everything we needed — even a baby tub and crib for our little ones. The hosts were very proactive and awesome to communicate with. Highly recommend!

Family- and pet-friendly home rentals

Top guest favourite
Home in Roncesvalles Village
5 out of 5 average rating, 43 reviews

High Park Lux: Sauna •King Bed •Family Friendly

MeghanRating, 5 stars1 month ago
Couldn’t have asked for a better host or place to stay. Esther and Sebastian were thoughtful and kind. Their home is stunning and has everything you could possibly need! The kitchen is so well appointed. We would definitely stay again and highly recommend this spot if you’re visiting Toronto!!
Superhost
Bungalow in Vaughan
4.84 out of 5 average rating, 44 reviews

Spacious, Bright 3 BEDS, 3 BATHS ♥ of Woodbridge

JenniferRating, 5 stars5 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.
Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 72 reviews

The Beach House Licence#: STRTT-2024-028

AtifRating, 5 stars3 months ago
Place was nice amd cosy for our family break in winter. Great toys collectiom for 2 years old, good books collection for older kids. Only downside was that it didn't have microwave which was tricky with 2 yr old especially when trying to warm up milk quickly. TV could have been bigger fpr the space but it was still good enough. Ian was very helpful and responsove during our stay, he got snow cleaned promptly during our stay.
Top guest favourite
Home in Ajax
4.96 out of 5 average rating, 28 reviews

3 bedroom bungalow in South Ajax

SamoriaRating, 5 stars2 weeks ago
my stay at Mrinals place was amazing! it looks exactly like the photos and was so clean. my family stayed here before moving out of the country and it was literally stocked with anything you’d need! anything we needed in the kitchen they had as well as laundry detergent and cleaning supplies. there was so many extra towels, sheets, and bedding. the check in was super easy and everything was exactly like the photos. The driveway has good space as well, me and my family were able to fit 2 SUV’s. Mrinal was an amazing host and very responsive and kind. I highly recommend!
Guest favourite
Home in Richmond Hill
4.89 out of 5 average rating, 151 reviews

Luxury 5 beds, 6 Baths custom home

FarhanRating, 5 stars2 weeks ago
Jay’s place was great for our family. Big space, lots of rooms, nice big kitchen. Bring more towels if you’re a big group. One of the showers was leaking to the floor below (Jay was really responsive to get this fixed, which he said he’d do after our visit). Kitchen is huge and definite plus if you’re with a big group, was a nice place to gather each morning and make breakfast together! Well stocked, though missing a basic frying pan. If you have elderly family, the stairs are a bit difficult to navigate. And lots of sharp edges around if you have little kids. Overall worked out well for our multi generation family trip!
Top guest favourite
Tiny home in Schomberg
4.99 out of 5 average rating, 204 reviews

SNAKE CABIN(rustic, 'off-the-grid')

MattRating, 5 stars1 month ago
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!
Guest favourite
Guest suite in Toronto
4.89 out of 5 average rating, 232 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

BruceRating, 5 stars3 days ago
My hosts Lucy and Don were completely accommodating, communicative, and responsive. Coming and going was a breeze. A completely outfitted kitchen with all that you'd need. The space offers total privacy. A quiet, but lively-enough neighborhood, steps away from Yonge St. It checked off all the boxes and I'm very satisfied with the experience and my stay.
Guest favourite
Apartment in Downtown Toronto
4.92 out of 5 average rating, 236 reviews

Vibrant downtown place

AbdelrahmanRating, 5 stars1 month ago
In his headline, Alex says, "I'm a professional (electrical engineer) and I'll be a good host." Alex is an electrical engineer and was a good host, as simple as that. The place was right next to the subway, in a very walkable area with lots of nice distanations nearby. Would definitely consider staying there again.

Family-friendly home rentals with a pool

Guest favourite
Apartment in Downtown Toronto
4.93 out of 5 average rating, 216 reviews

College Park :2Bd+2bth + Free parking

JacRating, 5 stars2 weeks ago
Arjun's place does exactly what it says on the tin. Located in a very convenient downtown location you are walking distance to Yonge and Bloor, Queens Park, or the Eaton's Centre. There are excellent grocers and coffee shops nearby. Public transportation is plentiful. We thought about renting a car and realised we didn't need one. The flat itself is older but has all the conveniences one would expect. Overall a pleasant stay.
Superhost
Apartment in Downtown Toronto
4.7 out of 5 average rating, 307 reviews

2 BDRM + 2 BATH + Free Parking - MTCC, CN, Jays!

SydneyRating, 5 stars4 months ago
We found Krishna’s place after having a horrendous experience at another air bnb and having to cancel it, and we had such a great experience here. It was clean, cozy, easy to check in, and within walking distance of so many great things. Krishna was very responsive and helpful whenever we needed anything. Would definitely stay here 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
Apartment in Downtown Toronto
4.87 out of 5 average rating, 326 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

JuliaRating, 5 stars1 month ago
Lovely place , felt right at home . Crystal was very helpful and responsive, given it was a very last minute booking. The street was very quiet and so was the building itself . Very cozy getaway in the heart of downtown Toronto for an incredibly good price . Thank you so much for making our short stay nothing short of AMAZING !
Guest favourite
Apartment in Downtown Toronto
4.97 out of 5 average rating, 237 reviews

Chic, High-Rise Apartment with CN Tower Views

SheaRating, 5 stars5 months ago
We had an excellent stay at Virginia’s place! Four of us came to Toronto for a concert at the Rodger’s Centre which was just across the street. The unit was quite a bit bigger than I expected! There was plenty of room for all four of us, we never felt crowded. We were able to walk to a huge variety of restaurants and activities. Virginia was beyond kind and welcoming. Super quick to respond and easy to communicate with! I would highly recommend staying with Virginia to anyone coming to Toronto!
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.
Top guest favourite
Home in Scarborough
4.86 out of 5 average rating, 42 reviews

Fantastic Family Get Away- sleeps 8

HeatherRating, 5 stars8 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 :)

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

  • Total rentals

    80 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

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