
Family-friendly vacation rentals in Keswick, Georgina
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Top-rated family-friendly rentals in Keswick, Georgina
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Popular amenities for Keswick, Georgina family-friendly rentals
Family-friendly home rentals with a hot tub

Mid-Century Kawartha Lakefront Estate
Jeremy's home in the Kawartha's was absolutely perfect for our 2 families and young children. From the moment we arrived we felt so at home! The property is stunning, nestled amongst the trees, though wide open and bright- there is generous deck space, a lawn for kids to run around on (as well as a zip line, swing and hammocks!!) and a sweet meandering path that leads to a quiet lake and dock. The home itself has a comfortable, spacious and relaxed vibe. It's mid century, art filled and modern. The kitchen has everything you could possibly need for creative cooking, and the amenities in general are generous- from board games to water sports, sauna and hot tub. While there we had rainy days and colder days, but there was always so much to do and explore that every day was rich. This home would also be a perfect winter getaway.. maybe one day!

Great Davenport Hillcrest House
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

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!

College Park :2Bd+2bth + Free parking
My husband and I were travelling with our 7-year-old son and Arjun’s condo was perfect. It was a great location, we didn’t have to drive anywhere all week. The local restaurants were amazing and while street noise could be heard in the condo the building itself was quiet. The apartment was clean, well stocked and the beds were comfortable! Based off Arjun’s detailed instructions it was easy to access the amenities such as parking and the pool (which was warm and clean!) We would definitely stay here 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
Family- and pet-friendly home rentals

Beautiful Riverside Country Apartment
Excellent place to stay for the night, very well priced, easy to find and was very clean and clutter free. Had easy access to internet and tv without issues. Wendy was very responsive and accommodating.

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka
DJ's place is a beautiful location and as described. DJ was also accommodating to allow an extra dog. Our weekend away was very enjoyable. I thought there could have been better communication between us and the host/co hosts. There were times where my messages were read immediately but responded to over 24 hours later, or ignored entirely. There were no issues with the place itself. I would return again.

Cozy one bedroom apartment in Roncesvales village
Seher is a sweetheart, very pleasant and friendly, she made us feel at home. We had an emergency and needed to book her house and she was very helpful from the beginning. The accommodation is extremely cozy, organized and very clean. The Dundas West station on the green line is just a 7-10 minute walk away and there are bus and streetcar lines available. Simply the perfect place to stay in Toronto with all the convenience, security and comfort we need during a trip. I highly recommend it.

Country Cabin for Long and Short Stays King bed
Peaceful escape that’s close to the city. It’s nice to have hotel-like amenities but also privacy and a full kitchen

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 !!!

Charming Century Home Close to Vibrant Shops
Lovely home for a family stay in an incredibly convenient location.

Entire House w/ Games Room-by Ski Hills & Downtown
We stayed here during Snowmaggedon' 25 and the cozy place made it more enjoyable. We even got stuck twice due to lot of snow, but the neighbors in the area were very helpful and it just became another fun snow activity. Location is close to the good snow resorts in area and offers a lot of activities to do. The place was clean and pet friendly. All of us and the our pup had a great weekend. Highly recommended for ski/snow sport getaways.

The Islandview
We had a great time at Corals cottage. The cottage is pet friendly, very conveniently located close to LCBO, grocery stores and Casino Rama. private access to lake and very clean. highly recommended. we loved our winter stay.Thanks Coral.
Family-friendly home rentals with a pool

Hot Tub & Cozy Fireplace - Headwaters Retreat
Cozy cozy!. Really close to the Millcroft Inn and Spa. Susan was wonderful and very responsive. Would come back 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!

The Trails Retreat (Private Cabin)
We had the most peaceful stay, we were arriving in a snow storm and Jill was just a fantastic host! She ensured to shovel clear paths for us and ensured we had what we needed. The cottage was the perfect spot to relax and be cozy. Thank you so much for having us!

All Season Waterfront Retreat with Pool & Hot Tub
Gary & Mina were excellent hosts. They greeted us for check in and where very accommodating. Any questions we had were quickly answered via the AirBNB app. The house was full of character and had lots of things to do indoors and outdoors. The kitchen was well stocked with supplies, utensils and kitchen wares. There was a washer/dryer centrally located which was great for towels and the Weber BBQ was in top notch condition. Water toys well maintained (2 kayaks, 1 paddle board, 1 canoe and 1 paddle boat). Pool and hot tub worked great, which was a must for our cottage getaway.

Sunny Pines Farm Studio Tennis Court/Bruce Trail
Fantastic property with the back fields. Our dogs had a blast. Some fantastic options for food around. Had an unexpected issue during our stay that is out of their control. They were very responsive and reasonable to communicate with. Will still come back and certainly recommend to others.

Sweet Memories of Georgian Bay
Idyllic gem on Georgian bay. Perfect for a small family getaway by the lake. The resort pool is a big plus for the kids. Beautiful surroundings and stunning sunsets. Jefferson is a great host. Very friendly and responsive. He kindly accommodated our request.

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

BEST VIEW in the City! Luxury condo
The city view from the apartment was breathtaking! The apartment and building were both immaculate. So easy to get around the city from this location. We absolutely loved our stay!
Quick stats about vacation rentals that are family-friendly in Keswick, Georgina
Total rentals
40 properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
820 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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