Family-friendly vacation rentals in Keswick, Georgina

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Keswick, Georgina

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Jan 27 – Feb 3

G$37,090 GYD per night

Guest favorite

Tiny home in Mono

4.94 out of 5 average rating, 152 reviews

Tiny home Soaring Heart Wellness Spa

A clean, bright space with high ceilings, privacy, and charm overlooking our Herbal Tea Garden. You can hike the Bruce Trail, relax by our pond or cycle through the Dufferin County Forest. Relax in the hot tub, book a massage, or enjoy a campfire under the stars. Check services online: Soaring Heart Wellness Inside is a bed, kitchenette, writing desk and sitting area. Outdoor is barbecue , firepit, and attached outhouse. Short walk to indoor bath Great local food and restaurants close by.

May 20 – 27

G$12,226 GYD per night

Guest favorite

Guest suite in Vaughan

4.92 out of 5 average rating, 542 reviews

Luxury Modern Two Bedrooms Basement Apartment

No 3rd party booking! No parties! No visitors! ARRIVING W/ EXTRA GUEST WILL GET CHARGED DOUBLE 24hr Exterior Surveillance Tons of upgrades and high end modern features! High ceiling above grade basement unit. Open concept living space include fireplace, smart TV(no cable, please use your streaming login), full kitchen, laundry and large wardrobe One parking on our driveway Free Wifi Enjoy scenic trails in Woodbridge 10min to Vaughan Mills outlets & Canada's wonderland 15min to Pearson airport

Jul 19 – 26

G$20,904 GYD per night

Guest favorite

Apartment in Wasaga Beach

4.95 out of 5 average rating, 357 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

Nov 25 – Dec 2

G$28,781 GYD per night

Guest favorite

Apartment in Horning's Mills

4.96 out of 5 average rating, 255 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Sep 5 – 12

G$16,616 GYD per night

Guest favorite

Apartment in Whitby

4.95 out of 5 average rating, 156 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!

Apr 27 – May 4

G$16,399 GYD per night

Guest favorite

Condo in Innisfil

4.84 out of 5 average rating, 171 reviews

Marina view at Friday Harbor 2bdm/2bth Pool option

Friday Harbour is a brand new all season resort just 1 hour and 15 minutes from Toronto. A perfect getaway without the long drive. Airbnb guests can now purchase a pass for the beach club pool! This Airbnb is an eight hundred square foot condo all newly furnished with king bed in master bedroom with ensuite bathroom, Queen bed in guest bedroom. Enjoy 65” Samsung Smart TV or sitting on the huge deck overlooking the marina and island homes. Board walk to beach, this place is amazing!

Apr 15 – 22

G$19,844 GYD per night

Guest favorite

Apartment in Oshawa

4.95 out of 5 average rating, 622 reviews

Just like home

This is an fully furnished basement apartment Quiet neighborhood close to bus stop, shopping and restaurants. Ten minute drive to Oshawa Center and downtown Oshawa. Reserve parking in driveway on left side. Breakfast ingredients are included; Eggs, Bacon, Cereal ,Toast, Coffee , Tea and etc. Our guests can rest assured that the bedding is washed and changed with each and every new guest, and for those who stay for a week or more , bedding is changed every five days or upon request.

Sep 24 – Oct 1

G$11,107 GYD per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private HotTub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

G$15,655 GYD per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Mar 4 – 11

G$34,938 GYD per night

Guest favorite

Apartment in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

Sep 28 – Oct 5

G$15,829 GYD per night

Guest favorite

Guesthouse in Schomberg

4.93 out of 5 average rating, 344 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

Jun 3 – 8

G$24,322 GYD per night