
Family-friendly holiday rentals in East Gwillimbury
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Top-rated family-friendly rentals in East Gwillimbury
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Popular amenities for East Gwillimbury family-friendly rentals
Family-friendly home rentals with a hot tub

Great Davenport Hillcrest House
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.

Amazing Modern house for all Families near OPG
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.

Luxury Modern House: Hot Tub, Gym & Steam Shower
Comfortable and clean in a lovely location. Host was extremely responsive. Highly recommend.

Mansions of Humberwood
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!

Family cottage just steps away from Lake Simcoe
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.

Orkney Beach 1 on the shores of Lake Simcoe
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!!

Stunning Waterfront Cottage
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

Waterside Haven: spacious retreat w/hot tub
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

High Park Lux: Sauna •King Bed •Family Friendly
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!!

Spacious, Bright 3 BEDS, 3 BATHS ♥ of Woodbridge
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.

The Beach House Licence#: STRTT-2024-028
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.

3 bedroom bungalow in South Ajax
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!

Luxury 5 beds, 6 Baths custom home
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!

SNAKE CABIN(rustic, 'off-the-grid')
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!

Midtown Luxury Yonge/Lawrence Close to Downtown
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.

Vibrant downtown place
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

College Park :2Bd+2bth + Free parking
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.

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

Downtown Markham Unionville
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!

Luxury heart of downtown by CN Tower/ MTCC/Union
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 !

Chic, High-Rise Apartment with CN Tower Views
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!

The Ridge Roost - Uxbridge Township
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.

Fantastic Family Get Away- sleeps 8
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!

Hidden Farm Escape in the Heart of the Kawarthas
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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- Rogers Centre
- Scotiabank Arena
- CN Tower
- Budweiser Stage
- Port Credit
- Horseshoe Resort
- University of Toronto
- Mount St. Louis Moonstone
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- CF Toronto Eaton Centre
- Snow Valley Ski Resort
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Royal Woodbine Golf Club
- Massey Hall
- Harbourfront Centre
- Yonge-Dundas Square
- Osler Bluff Ski Club
- Trinity Bellwoods Park
- Royal Ontario Museum
- Royal Alexandra Theatre
- BMO Field