Family-friendly holiday rentals in Keswick, Georgina

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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, 48 reviews

Great Davenport Hillcrest House

LindsayRating, 5 stars1 month ago
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!
Home in Windfields
4.44 out of 5 average rating, 9 reviews

Amazing Modern house for all Families near OPG

NathanRating, 5 stars77 months ago
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.
Guest favourite
Home in York
4.89 out of 5 average rating, 75 reviews

Luxury Modern House: Hot Tub, Gym & Steam Shower

ElizabethRating, 5 stars9 months ago
Comfortable and clean in a lovely location. Host was extremely responsive. Highly recommend.
Serviced apartment in Clearview

Creemore Estate Loft

VictoriaRating, 5 stars20 months ago
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.
Superhost
Cottage in Orillia
4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

AnnalisaRating, 5 stars33 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
Cottage in Orillia
4.84 out of 5 average rating, 31 reviews

Orkney Beach 1 on the shores of Lake Simcoe

KaylaRating, 5 stars8 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 stars10 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
Guest favourite
Tiny home in Mono
4.94 out of 5 average rating, 159 reviews

Tiny home in Mono

AngelaRating, 5 stars4 months ago
What inspired me to book this tiny cabin again was how peaceful the space feels. We’d benefited from treatments and classes with Ellen during a previous stay and I was excited to get to book with her this time and was not disappointed. Thank you Ellen, for your heart centred approach to hosting. It was great for me to be able to relax in your tiny cabin.

Family- and pet-friendly home rentals

Superhost
Bungalow in Orillia
4.87 out of 5 average rating, 248 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

Trevor and KristineRating, 5 stars2 weeks ago
Another prefect stay at DJs place. We will definitely be booking again next time we are in the area.
Superhost
Cottage in Kawartha Lakes
4.79 out of 5 average rating, 105 reviews

Serenity by the Lake: Lake Waterfront Cottage

TaylorRating, 5 stars1 week ago
Jaan & Nithya were great hosts. The place was beautiful and they were very helpful and responsive when we had any questions! Great place for a family getaway on the lake. Definitely recommend!
Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 72 reviews

The Beach House Licence#: STRTT-2024-028

AtifRating, 5 stars6 months ago
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.
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 stars9 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
4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

DavidRating, 5 stars2 months ago
Great place, will stay again
Guest favourite
Cottage in Kawartha Lakes
4.98 out of 5 average rating, 81 reviews

Beautiful Balsam Lake Retreat-2Hammocks on Balsam

TaraRating, 5 stars6 months ago
Beautiful cottage with a spectacular view of the lake! Very quiet and peaceful for rest and relaxation. The fireplace made the cottage even more cozy on some very cold winter days during our stay. The bed was very comfortable and the entire cottage was well set up for a relaxing atmosphere. Everything was easy to find and anything you could possibly need was there. We loved that amenities like grocery stores and restaurants were close by and easily accessible.
Guest favourite
Home in Richmond Hill
4.89 out of 5 average rating, 157 reviews

Luxury 5 beds, 6 Baths custom home

StephenRating, 5 stars3 days ago
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!
Superhost
Home in Creemore
4.97 out of 5 average rating, 34 reviews

Mulmur Getaway, outside of Creemore

CarolRating, 5 stars8 months ago
Great place for a peaceful getaway in beautiful surroundings just a few minutes from town. Can’t say enough good things! Comfortable and cozy in combination with spacious, airy and bright. Everything you need. Lots of space with walking paths for kids and dogs. Great working kitchen. Huge deck with great bbq. Beautifully kept property. Responsive and friendly host.

Family-friendly home rentals with a pool

Apartment in North York
5 out of 5 average rating, 12 reviews

Charming One Bedroom Condo

EleftheriaRating, 5 stars3 months ago
Great location, comfortable apartment. Host was very responsive and helpful, Amazing views!
Guest favourite
Guest suite in Orangeville
4.92 out of 5 average rating, 771 reviews

Hot Tub & Pool Getaway - Headwaters Retreat

TeresaRating, 5 stars4 days ago
Susan’s place was clean, well-equipped and pristine. It was indeed a beautiful retreat, complete with hot tub and a pool. Communication with her was always pleasant and accommodating. Everything was well thought-out.
Guest favourite
Apartment in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars3 months 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!
Top guest favourite
Cabin in Mono
4.95 out of 5 average rating, 309 reviews

The Trails Retreat (Private Cabin)

CarolynRating, 5 starstoday
10 STAR!!! Amazing property! Impeccably maintained gorgeous cabin (rustic/modern and very classy) and surrounding grounds. So lovely! The hosts have thought of absolutely everything. I didn't want to leave! Now on my bucket list to return, hike Mono Cliffs then relax by the sparling clean pool. The Trails Retreat Cabin is an affordable deluxe property that you really should treat yourself to!
Guest favourite
Chalet in Creemore
5 out of 5 average rating, 26 reviews

Creemore/Mulmur Country Estate Pool/Tennis/Hot Tub

RonenRating, 5 stars10 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!
Top guest favourite
Guest suite in Orangeville
4.97 out of 5 average rating, 161 reviews

Your Peaceful Santuary in Nature

JillRating, 5 stars4 months ago
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!
Guest favourite
Home in Uxbridge
4.85 out of 5 average rating, 91 reviews

The Ridge Roost - Uxbridge Township

JulieRating, 5 stars2 weeks ago
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.
Top guest favourite
Home in Scarborough
4.86 out of 5 average rating, 43 reviews

Fantastic Family Get Away- sleeps 8

SarahRating, 5 stars2 weeks ago
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 holiday rentals that are family-friendly in Keswick, Georgina

  • Total rentals

    40 properties

  • Nightly prices starting at

    $13 SGD 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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  2. Canada
  3. Ontario
  4. Georgina
  5. Keswick
  6. Family-friendly rentals