
Family-friendly vacation rentals in Keswick, Georgina
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Top-rated family-friendly rentals in Keswick, Georgina
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Keswick, Georgina family-friendly rentals
Family-friendly home rentals with a hot tub

Great Davenport Hillcrest House
I’m almost afraid to leave an accurate review because this place is such a hidden gem I don’t want to compete when we try to stay here again. This home is so beautiful, well stocked, cozy, incredible neighbourhood, and I could go on and on. Ottilie was a thoughtful host with excellent communication and she opened her home up to my family. I will never try to stay anywhere else in Toronto! Thank you, Ottilie!

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.

Creemore Estate Loft
Wonderfully accommodating and helpful hosts that went out of their way to make sure we had everything we needed and much more! We have a lovely time.

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

Couples retreat w/hot tub: Romantic Getaway
Brandy is a fantastic, responsive host. I would recommend her property to anyone! It was exactly what we needed. Thanks Brandy!
Family- and pet-friendly home rentals

Serenity by the Lake: Lake Waterfront Cottage
We have booked twice at this place and we just love it . There’s too much to do and the house is beautiful.

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!

Charming Century Home Close to Vibrant Shops
Beyond the house itself, the hosts were truly outstanding. They were not only extremely courteous but also incredibly responsive to any questions we had, making us feel welcomed and well-cared for throughout our entire stay. Their genuine hospitality added significantly to the positive experience. If you're looking for a unique and memorable stay in Toronto, especially if you appreciate the charm of a well-preserved historic home combined with the warmth of exceptional hosts, look no further. We highly recommend this house.

1950's Romantic & Whimsical cottage on Gull River
Beautiful place! Can’t wait to return. The fishing is fantastic here! Thank you so much Stephanie you are a fantastic host !!!

Entire House w/ Games Room- by Beaches & Downtown
Great place, will stay again

Luxury 5 beds, 6 Baths custom home
Perfect spot for a group trip. Quiet neighborhood, close to the TTC for easy access to downtown. Jay was awesome at handling our request to drop off our luggage prior to our scheduled check-in time. Would definitely stay again!

Midtown Luxury Yonge/Lawrence Close to Downtown
I stayed here with my family for two nights while visiting the city! The space was super nice and welcoming. Spotless, updated, and comfortable. About a 10min walk to transit but straight forward and the neighbourhood felt very safe.
Family-friendly home rentals with a pool

Charming One Bedroom Condo
Great location, comfortable apartment. Host was very responsive and helpful, Amazing views!

College Park :2Bd+2bth + Free parking
This condo was a great location, especially for guests visiting U of T or wanting to be in the heart of Toronto with easy access to adjoining neighborhoods. The apartment had great views of the area, was comfortable, clean with excellent amenities including a superb pool and exercise area on the 2nd floor of the building. Arjun is a most friendly and reliable host. I look forward to staying at his condo for an upcoming visit to Toronto.

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!

The Trails Retreat (Private Cabin)
Jill And Chef Jeff are A++ hosts. They were very responsive to requests and inquires. Their property is a slices of heaven; quiet, and peaceful. Bird songs to start your day. Chef Jeff's culinary delights had us indulging in his masterpieces the next day. I HIGHLY recommend you working with Chef for 1 nights dinner. Thank you to this fabulous couple.

Creemore/Mulmur Country Estate Pool/Tennis/Hot Tub
Had the best time for our bachelor party at Mountain Ash Farm! Patricia and Ron were responsive and super helpful. Will be coming back here!

Your Peaceful Santuary in Nature
Would highly recommend! A very spacious spot with lots of activities and lovely surroundings. The place is very cozy with the wood burning stove and plethora of candles. Annette was very pleasant, responsive and accommodating! We had a great time playing with her dogs in the snow. We will be back!

The Ridge Roost - Uxbridge Township
Enjoyed being in the country. The place was very spacious, big kitchen with everything you need & the beds were comfortable. Stephen was a great host, very responsive and being close by, he was able to help with anything you need. The place is well situated between Port Perry and Uxbridge.

Fantastic Family Get Away- sleeps 8
We had a lovely stay in Liz’s house, the pool was great for the kids, we felt right at home. Liz was very responsive to any queries I had. We would definitely return if we find ourselves back in the area. The piano was a big hit too!
Quick stats about vacation rentals that are family-friendly in Keswick, Georgina
Total rentals
40 properties
Nightly prices starting at
G$2,092 GYD before taxes and fees
Total number of reviews
840 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Osler Bluff Ski Club
- Horseshoe Resort