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

Guest favorite
A cozy living area features a comfortable sofa paired with two black chairs, set against built-in bookshelves filled with books and art. A decorative chandelier hangs above, while a fireplace serves as a focal point, surrounded by a tasteful arrangement of art on the walls.
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!
A spacious living area is depicted with a cozy couch adorned with patterned cushions. A decorative Buddha statue rests above a modern fireplace, enhancing the serene ambiance. Large windows allow natural light to fill the room, illuminating the hardwood floors and inviting seating arrangement.
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 favorite
A modern living area showcases a spacious sectional sofa and a coffee table featuring unique wooden craftsmanship. Natural light floods the room through large glass doors, highlighting greenery from potted plants. A mounted television and built-in shelving with books are positioned on the wall.
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.
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
A hot tub is positioned outdoors, providing a clear view of Lake Simcoe. The bubbling water contrasts with the calm lake backdrop, where trees line the shore. Nearby, seating is visible, enhancing the relaxing environment within the cottage's outdoor space.
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 favorite
The exterior of the cottage is visible, showcasing a light blue structure with a spacious sunroom and a matching shed. A wooden dock extends toward the water, framed by a rocky shoreline. Outdoor seating includes two lounge chairs and a fire pit area with colorful chairs.
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!!
A spacious living area is highlighted by large windows that provide natural light. A wooden dining table sits center stage, surrounded by white upholstered chairs. A stone fireplace adds character to the room, complemented by neutral-toned furnishings arranged for relaxation.
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 favorite
A private hot tub bubbles gently under a clear sky, surrounded by thick snow covering the ground. In the background, a small shed is visible, alongside snow-laden trees providing a sense of winter tranquility.
Cottage in Orillia
4.91 out of 5 average rating, 101 reviews

Couples retreat w/hot tub: Romantic Getaway

EthanRating, 5 stars3 months ago
Brandy is a fantastic, responsive host. I would recommend her property to anyone! It was exactly what we needed. Thanks Brandy!

Family- and pet-friendly home rentals

Superhost
A tranquil waterfront view is captured, showcasing a grassy area leading to the lake. Four black Adirondack chairs are arranged facing the water, under a large tree. A wooden dock extends into the lake, with a ladder visible, inviting reflection and relaxation.
Cottage in Kawartha Lakes
4.79 out of 5 average rating, 104 reviews

Serenity by the Lake: Lake Waterfront Cottage

Juan FelipeRating, 5 stars3 weeks ago
We have booked twice at this place and we just love it . There’s too much to do and the house is beautiful.
Guest favorite
Cottage in Tiny
4.96 out of 5 average rating, 72 reviews

The Beach House Licence#: STRTT-2024-028

AtifRating, 5 stars5 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 favorite
A comfortable living area features a sectional sofa arranged around a glass coffee table. Two art pieces adorn the wall, and natural light filters through large, sheer curtains. A television is mounted on a light wooden console, enhancing the space's modern aesthetic.
Home in Ajax
4.93 out of 5 average rating, 30 reviews

3 bedroom bungalow in South Ajax

SamoriaRating, 5 stars2 months ago
my stay at Mrinals place was amazing! it looks exactly like the photos and was so clean. my family stayed here before moving out of the country and it was literally stocked with anything you’d need! anything we needed in the kitchen they had as well as laundry detergent and cleaning supplies. there was so many extra towels, sheets, and bedding. the check in was super easy and everything was exactly like the photos. The driveway has good space as well, me and my family were able to fit 2 SUV’s. Mrinal was an amazing host and very responsive and kind. I highly recommend!
Top guest favorite
A cozy living room features a vintage sofa adorned with decorative pillows, complemented by a plush armchair. A large window is framed by soft drapes, allowing natural light to brighten the space. An elegant coffee table holds a decorative tray, enhancing the inviting ambiance.
Home in Toronto
4.9 out of 5 average rating, 136 reviews

Charming Century Home Close to Vibrant Shops

RigoRating, 5 stars2 weeks ago
Beyond the house itself, the hosts were truly outstanding. They were not only extremely courteous but also incredibly responsive to any questions we had, making us feel welcomed and well-cared for throughout our entire stay. Their genuine hospitality added significantly to the positive experience. If you're looking for a unique and memorable stay in Toronto, especially if you appreciate the charm of a well-preserved historic home combined with the warmth of exceptional hosts, look no further. We highly recommend this house.
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 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
The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.
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 favorite
A modern living area is presented with soft white seating arranged around a central coffee table. Shelves hold decorative items, while a large window allows natural light to fill the space, offering views of greenery outside. A mounted television complements the inviting atmosphere.
Home in Richmond Hill
4.89 out of 5 average rating, 157 reviews

Luxury 5 beds, 6 Baths custom home

StephenRating, 5 stars1 day 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!
Guest favorite
A living room features a gray sofa accented with decorative cushions, paired with two mid-century modern chairs. A large window allows natural light to illuminate the space. A mounted flat-screen TV and an electric fireplace are visible, enhancing the cozy atmosphere.
Guest suite in Toronto
4.89 out of 5 average rating, 239 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

RachelRating, 5 stars1 week ago
I stayed here with my family for two nights while visiting the city! The space was super nice and welcoming. Spotless, updated, and comfortable. About a 10min walk to transit but straight forward and the neighbourhood felt very safe.

Family-friendly home rentals with a pool

A panoramic view showcases the city skyline against a colorful twilight sky, with soft pink and blue hues filling the horizon. Lush trees and urban structures create a tranquil contrast, highlighting the expanse of the neighborhood below.
Condo 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 favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 220 reviews

College Park :2Bd+2bth + Free parking

JeanneRating, 5 stars1 week ago
This condo was a great location, especially for guests visiting U of T or wanting to be in the heart of Toronto with easy access to adjoining neighborhoods. The apartment had great views of the area, was comfortable, clean with excellent amenities including a superb pool and exercise area on the 2nd floor of the building. Arjun is a most friendly and reliable host. I look forward to staying at his condo for an upcoming visit to Toronto.
Guest favorite
The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.
Condo 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 favorite
A clear view of the heated swimming pool is presented, surrounded by a well-manicured lawn. Two lounge chairs are positioned beside the pool, offering a relaxing space. Lush greenery and trees create a natural backdrop, enhancing the serene atmosphere of the outdoor area.
Cabin in Mono
4.95 out of 5 average rating, 309 reviews

The Trails Retreat (Private Cabin)

PetrinaRating, 5 stars1 day ago
Jill And Chef Jeff are A++ hosts. They were very responsive to requests and inquires. Their property is a slices of heaven; quiet, and peaceful. Bird songs to start your day. Chef Jeff's culinary delights had us indulging in his masterpieces the next day. I HIGHLY recommend you working with Chef for 1 nights dinner. Thank you to this fabulous couple.
Guest favorite
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 favorite
A clear swimming pool is surrounded by a concrete patio. A small shed is visible in the background, accompanied by green plants and a watering can. Lounge chairs are placed along the edge of the pool, creating a welcoming outdoor space.
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 favorite
A serene outdoor area features a passive-solar heated pool surrounded by lush greenery and tall trees. The pool deck, partially visible, includes a slide and seating areas, offering a tranquil retreat in a natural setting.
Home in Uxbridge
4.87 out of 5 average rating, 90 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 favorite
A workspace is positioned with a sleek desk and ergonomic chair, complemented by wall-mounted shelves displaying various items. Natural light fills the room through large windows. A plush rug and a cozy sofa create a comfortable atmosphere, while a colorful playhouse stands nearby.
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 vacation rentals that are family-friendly in Keswick, Georgina

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$2,092 GYD 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

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