
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

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

HotTub & Fireplace Getaway - Headwaters Retreat
We enjoyed our stay at Susan's place! Quiet, private and had a real homey feel... and the hot tub was a nice touch! would certainly rent again!

College Park :2Bd+2bth + Free parking
Absolute awesome stay at Arjun’s. The place is cozy, comfy and packed with all you need for a perfect get away. Arjun is a very reactive and accommodating host. He was there during the checkin process, a first time for us. Usually you deal with a code or a key-box… Thank you Arjun, we will definitely book your condo 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!

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.

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.

Waterside Haven: spacious retreat w/hot tub
We had a wonderful time at this beautiful house. There were plenty of amenities and lots to do nearby. It was spacious and the hot tub was the perfect touch. We were very happy with everything ❤️

Serenity Suite w/Sauna-Your Entire Apt Awaits You
I will always recommend this place to stay. I have stayed here 3 times now over the years and it's great. Exactly as described, and the sauna is fabulous.
Family- and pet-friendly home rentals

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.

Country Cabin Escape | King Bed | Pet Friendly
Sure! Here's a review you can use: "I had a perfect stay at this Airbnb. The space was exactly as described—peaceful, serene, and surrounded by nature. It provided the perfect escape from the hustle and bustle. The property was clean, fresh, and well-maintained, making it a truly relaxing environment. The surroundings were beautiful, offering a calming atmosphere. I highly recommend this place for anyone looking for a tranquil getaway. Would definitely stay again!"

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
I spent a full week here. This is an older home but has some nice renovations done and it's really clean! It's an older neighbourhood but I felt safe and had no concerns out walking. It's a very quiet, private area but really close to the highway which was great for access to my office. I would definitely stay again. I was even accommodated for an additional night when I made an error in my booking. Thank you for a great stay! 🙏

Designer Condo with beautiful harbour view.
Staying at Carolyn’s place was an excellent choice! Carolyn was very responsive, communicative and accommodating. The instructions provided were simple and easy to follow. The unit is stunning! You can tell it was designed very well & thoughtful pieces throughout the unit. The unit was really clean. The area had amazing restaurants & shops to check out. I plan to be back during the summer!

Luxury 5 beds, 6 Baths custom home
Another fantastic stay at Jay’s place! He is very responsive and quick to restock necessities. House has plenty of space for everyone with multiple living areas. Looking forward to our next stay!

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
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!
Family-friendly home rentals with a pool

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

The Trails Retreat (Private Cabin)
This cabin was a total delight! It was peaceful, surrounded by nature and everything we were looking for. The cabin itself is spacious, clean, with great amenities and equipped with games and books so you’ll never experience a dull moment. I highly recommend this place!

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!

Sunny Pines Farm Studio Tennis Court/Bruce Trail
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.

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.

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!

Scenic cottages (2bdrm) south shore Sturgeon Lake
We had a great time Gord’s place!The cabin is spacious, cozy, and functional with a fully equipped kitchen and two full bathrooms. Great location with easy access to the pool and a beautiful view of the lake where you can enjoy stunning sunsets right from the deck. The grounds are meticulously maintained with beautiful flowerbeds and ample lakeshore space, very quiet,creating a peaceful and tranquil atmosphere. Gord and his family are exceptional hosts—friendly, respectful, accommodating, and quick to respond to any questions we had. Gord even offered a flexible check-in time and provided two heaters for a couple of chilly nights. His local recommendations for nearby attractions were also greatly appreciated. Additionally, their thoughtful gesture of providing a play kitchen structure with toys made our toddler incredibly happy. We highly recommend Gord’s place to anyone seeking a peaceful retreat surrounded by nature. Thank you for a memorable stay—we look forward to returning!
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
Destinations to explore
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- Blue Mountain Village
- Budweiser Stage
- Port Credit
- Horseshoe Resort
- Mount St. Louis Moonstone
- University of Toronto
- Snow Valley Ski Resort
- CF Toronto Eaton Centre
- Toronto Zoo
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- Massey Hall
- Royal Woodbine Golf Club
- Yonge-Dundas Square
- Osler Bluff Ski Club
- Royal Ontario Museum
- Trinity Bellwoods Park
- Lakeridge Ski Resort
- Hockley Valley Resort - Golf, Spa and Ski
- Georgian Bay Islands National Park