Family-friendly vacation rentals in Keswick, Georgina

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Popular amenities for Keswick, Georgina family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cottage in Kinmount
4.91 out of 5 average rating, 35 reviews

Mid-Century Kawartha Lakefront Estate

KellyRating, 5 stars7 months ago
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!
Guest favorite
Home in Midtown
4.96 out of 5 average rating, 46 reviews

Great Davenport Hillcrest House

DylanRating, 5 stars4 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
Guest favorite
Home in York
4.89 out of 5 average rating, 75 reviews

Luxury Modern House: Hot Tub, Gym & Steam Shower

ElizabethRating, 5 stars6 months ago
Comfortable and clean in a lovely location. Host was extremely responsive. Highly recommend.
Condo in Rexdale
4.7 out of 5 average rating, 53 reviews

Mansions of Humberwood

LauraRating, 5 stars2 months ago
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!
Guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 211 reviews

College Park :2Bd+2bth + Free parking

LindseyRating, 5 stars3 months ago
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.
Superhost
Cottage in Orillia
4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

AnnalisaRating, 5 stars30 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 favorite
Cottage in Orillia
4.83 out of 5 average rating, 30 reviews

Orkney Beach 1 on the shores of Lake Simcoe

KaylaRating, 5 stars5 months ago
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!!
Cabin in Brechin
4.86 out of 5 average rating, 7 reviews

Stunning Waterfront Cottage

StephanieRating, 5 stars7 months ago
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

Top guest favorite
Apartment in Horning's Mills
4.96 out of 5 average rating, 283 reviews

Beautiful Riverside Country Apartment

JordanRating, 5 stars2 weeks ago
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.
Guest favorite
Bungalow in Orillia
4.87 out of 5 average rating, 239 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

BrittaneyRating, 5 stars2 days 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 favorite
Home in Roncesvalles Village
4.92 out of 5 average rating, 146 reviews

Cozy one bedroom apartment in Roncesvales village

BrunaRating, 5 stars1 week ago
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.
Guest favorite
Guesthouse in Schomberg
4.93 out of 5 average rating, 411 reviews

Country Cabin for Long and Short Stays King bed

GaryRating, 5 stars2 weeks ago
Peaceful escape that’s close to the city. It’s nice to have hotel-like amenities but also privacy and a full kitchen
Top guest favorite
Cottage in Kawartha Lakes
4.9 out of 5 average rating, 117 reviews

1950's Romantic & Whimsical cottage on Gull River

JulieRating, 5 stars5 months ago
Beautiful place! Can’t wait to return. The fishing is fantastic here! Thank you so much Stephanie you are a fantastic host !!!
Top guest favorite
Home in Toronto
4.89 out of 5 average rating, 133 reviews

Charming Century Home Close to Vibrant Shops

EleanorRating, 5 stars3 months ago
Lovely home for a family stay in an incredibly convenient location.
Superhost
Home in Barrie
4.81 out of 5 average rating, 248 reviews

Entire House w/ Games Room-by Ski Hills & Downtown

VyomRating, 5 stars3 weeks ago
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.
Superhost
Cottage in Washago
4.8 out of 5 average rating, 244 reviews

The Islandview

NitishRating, 5 stars1 month ago
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

Top guest favorite
Guest suite in Orangeville
4.92 out of 5 average rating, 737 reviews

Hot Tub & Cozy Fireplace - Headwaters Retreat

JessicaRating, 5 stars1 week ago
Cozy cozy!. Really close to the Millcroft Inn and Spa. Susan was wonderful and very responsive. Would come back here again.
Guest favorite
Condo in Unionville
4.91 out of 5 average rating, 113 reviews

Downtown Markham Unionville

AndreaRating, 5 stars1 week 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!
Guest favorite
Cabin in Mono
4.95 out of 5 average rating, 299 reviews

The Trails Retreat (Private Cabin)

LillyRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Sebright
5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

AaronRating, 5 stars6 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.
Guest favorite
Guesthouse in Orangeville
4.95 out of 5 average rating, 349 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Yu-HanRating, 5 stars2 months ago
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.
Guest favorite
Bungalow in Lafontaine Beach
4.9 out of 5 average rating, 50 reviews

Sweet Memories of Georgian Bay

FionaRating, 5 stars5 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 favorite
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

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

Joanna LRating, 5 stars8 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!
Top guest favorite
Condo in Downtown Toronto
4.94 out of 5 average rating, 82 reviews

BEST VIEW in the City! Luxury condo

HeatherRating, 5 stars2 months ago
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

    ﺩ.ﺇ37 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