
Family-friendly vacation rentals in Keswick
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Keswick
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

2 Bed-2Bath-Kitchen | Private | Family-Couple-Work
We have an ideal place for you regardless of work, pleasure, or family time. The recently renovated suite includes: - Separate keyless entry - 2 bedrooms with closets - Living room with 55" TV - Full kitchen with storage & dining - 2 full bathrooms (1 en suite) - 2 on-premises Parking - Laundry - WiFi & more FAST EV Charger-Check for availability ($15/charge) CENTRAL LOCATION! Steps to Upper Canada Mall, Groceries, Restaurants, Trails, Parks, Golf Course, Costco, Walmart, Highway, Go, & more

Four season glamping dome under the stars
Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Stylish, Modern 2nd Floor Private Apt. Quiet Area
Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

Adorable Entire Suite,Sep. Entry,1 Parking
Enjoy easy access to stores, restaurants and entertainment from this perfect location. Only 5 min. drive to GO Train & Bus Terminal with quick, convenient transport to Downtown Toronto, Canada’s Wonderland, etc. This lower level guest suite is fully equipped with own laundry, kitchenette with mini fridge, Induction 2 burner Cook Top Stove, microwave, toaster and coffee maker. Cozy Fireplace, 60” screen HD TV and Luxurious King Size Bed Safe Neighbourhood with walking trails and parks.

Granny's Cottage
Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

Private Loft w Sauna, Fireplace, Wi-Fi & Projector
Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Romantic Cabin N the Woods just 80km from CN Tower
This Romantic 1 bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Birthdays, Anniversaries, Honeymoons & Proposals! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom! Or simply enjoy a time away to re-connect with your loved one! Sit under stars Year Round in the modern new Hot tub after your run or walk on 200 acres of hilly trails 5kms from the cabin ( Brown Hill Tract)

Cozy apartment in Newmarket
This cozy home, located at Leslie and Mulock, is within walking distance of parks, grocery stores, and restaurants. It’s a short drive to Southlake Hospital, Historic Downtown Newmarket, the GO station, and Upper Canada Mall, Walking distance to Pickering College. Guests have full access to the first floor, featuring a living room, kitchen, dining room, and a private basement apartment, with a private bathroom. Perfect for a comfortable and convenient stay.

Modern, Private and Luxurious!
Welcome to our bright and stylish lower level unit in a friendly new development! You'll enjoy all the comforts of home in this cozy space. Located near Base Borden, the Honda Plant and Baxter Labs. 5 mins from Nottawasaga Inn. 30 mins to skiing at Snow Valley Ski Resort, Hockley Valley Resort, and Mansfield Ski Club. Right around the corner is an awesome community park that features a summer splash pad and a great winter tobogganing hill.

The Quiet Retreat
Welcome to our cozy suite, your perfect private retreat. Soft beige walls and warm lighting create a comforting atmosphere in our open-concept space. Unwind in the sleeping area or kick back in the living and dining areas with a good book or work. Our separate entrance ensures complete privacy, allowing you to come and go as you please. Make yourself at home in our warm and inviting place, your home away from home. License #BL2023-00257

1 Bedroom Hotel Style Short/Long term Available
Come stay at this brand new all-season, private & modern guest suite close to all Innisfil has to offer! 1.2 km away from Lake Simcoe, Big Cedar Golf Course & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

Lovely 2-bedroom at Friday Harbour
Friday Harbour Resort welcomes you to the start of something extraordinary. Friday Harbour was designed to be a destination. A destination you look forward to visiting all year round, where you can unwind and truly feel relaxed. Whether you arrive to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of way to enjoy your days.
Popular amenities for Keswick family-friendly rentals
Family-friendly home rentals with a hot tub

Kempenhaus- Lake Simcoe Cottage & Spa

Family Friendly | HOT TUB | Near Toronto & UOIT

Luxury Guest House with Private Hot Tub and Trails

South Geodome - Birchwood Luxury Camping

Serene Comfort. Hot Tub, Full Suite with Kitchen

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Spacious Hideaway in Nature

Hillside Haven: Serene Studio Retreat for 4
Family- and pet-friendly home rentals

Deerleap Glamping Dome

Studio Apartment

Lovely one bedroom guest suite in the country

Cozy Beeton Retreat - Gas Fireplace

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Romantic King Suite | Countryside | Pet Friendly

Orchard cottage, experience the farm in the city

The Chieftain Suite
Family-friendly home rentals with a pool

Farmhouse Guest Suite; Year round hot tub

Cozy Stays – Your Fall Getaway at Friday Harbour

The Hilton BnB Adult Luxury Suite

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Treehouse on private, isolated forest (300 acres)

Utopia villa and spa

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
When is the best time to visit Keswick?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $163 CAD | $192 CAD | $144 CAD | $125 CAD | $219 CAD | $213 CAD | $221 CAD | $260 CAD | $213 CAD | $184 CAD | $141 CAD | $213 CAD |
| Avg. temp | -7 °C | -6 °C | -1 °C | 6 °C | 12 °C | 17 °C | 20 °C | 19 °C | 15 °C | 9 °C | 3 °C | -3 °C |
Quick stats about vacation rentals that are family-friendly in Keswick

Total vacation rentals
Explore 40 vacation rentals in Keswick

Nightly prices starting at
Keswick vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Keswick vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Keswick rentals

4.7 Average rating
Keswick stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with outdoor seating Keswick
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- Pet-friendly rentals Keswick
- Cottage rentals Keswick
- House rentals Keswick
- Rentals with a washer and dryer Keswick
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- Family-friendly rentals Georgina
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- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Snow Valley Ski Resort
- Rouge National Urban Park
- Christie Pits Park
- Toronto City Hall
- Royal Ontario Museum




