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Family-friendly vacation rentals in Keswick, Georgina

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Keswick, Georgina family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Midtown
4.96 out of 5 average rating, 46 reviews

Great Davenport Hillcrest House

DylanRating, 5 stars5 months ago
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
Top guest favourite
Guest suite in Orangeville
4.92 out of 5 average rating, 744 reviews

HotTub & Fireplace Getaway - Headwaters Retreat

NathanRating, 5 stars5 days ago
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!
Guest favourite
Condo in Downtown Toronto
4.93 out of 5 average rating, 214 reviews

College Park :2Bd+2bth + Free parking

CarineRating, 5 stars1 month ago
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
Guest favourite
Condo 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
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
Home in Sebright
5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

AaronRating, 5 stars7 months ago
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.
Superhost
Cottage in Orillia
4.73 out of 5 average rating, 208 reviews

Waterside Haven: spacious retreat w/hot tub

JenniferRating, 5 stars3 months ago
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 ❤️
Guest favourite
Apartment in Whitby
4.96 out of 5 average rating, 224 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

AlannahRating, 5 stars1 week ago
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

Superhost
Bungalow in Orillia
4.87 out of 5 average rating, 240 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

BrittaneyRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in Schomberg
4.93 out of 5 average rating, 417 reviews

Country Cabin Escape | King Bed | Pet Friendly

ZalakbanuRating, 5 stars2 weeks ago
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!"
Top guest favourite
Cottage in Kawartha Lakes
4.9 out of 5 average rating, 117 reviews

1950's Romantic & Whimsical cottage on Gull River

JulieRating, 5 stars6 months ago
Beautiful place! Can’t wait to return. The fishing is fantastic here! Thank you so much Stephanie you are a fantastic host !!!
Superhost
Home in Barrie
4.8 out of 5 average rating, 251 reviews

Entire House w/ Games Room- by Beaches & Downtown

ConnieRating, 5 stars3 weeks ago
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! 🙏
Guest favourite
Condo in Innisfil
4.93 out of 5 average rating, 206 reviews

Designer Condo with beautiful harbour view.

AlexRating, 5 stars1 month ago
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!
Guest favourite
Home in Richmond Hill
4.89 out of 5 average rating, 150 reviews

Luxury 5 beds, 6 Baths custom home

LeslieRating, 5 stars3 weeks ago
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!
Top guest favourite
Tiny homes 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, 229 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

KatherineRating, 5 stars2 weeks ago
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

Condo in North York
5 out of 5 average rating, 11 reviews

Charming One Bedroom Condo

EleftheriaRating, 5 stars1 month ago
Great location, comfortable apartment. Host was very responsive and helpful, Amazing views!
Guest favourite
Cabin in Mono
4.95 out of 5 average rating, 301 reviews

The Trails Retreat (Private Cabin)

SwarnaRating, 5 stars5 days ago
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!
Guest favourite
Chalet in Creemore
5 out of 5 average rating, 26 reviews

Creemore/Mulmur Country Estate Pool/Tennis/Hot Tub

RonenRating, 5 stars8 months ago
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!
Guest favourite
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars1 week ago
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.
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.
Guest favourite
Bungalow in Lafontaine Beach
4.9 out of 5 average rating, 50 reviews

Sweet Memories of Georgian Bay

FionaRating, 5 stars6 months ago
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.
Guest favourite
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars9 months ago
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!
Cottage in Kawartha Lakes
4.71 out of 5 average rating, 21 reviews

Scenic cottages (2bdrm) south shore Sturgeon Lake

JuliaRating, 5 stars9 months ago
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

  1. Airbnb
  2. Canada
  3. Ontario
  4. Georgina
  5. Keswick
  6. Family-friendly rentals