Family-friendly holiday rentals in Keswick

Bed of Roses Airbnb. 45 mins N of Toronto. Hot tub

*Requests typically replied to within 15 mins during the day.* Private bright 2 bedroom basement (sleeps 4 & no shared areas), 45 minutes N of Toronto. We live in a safe neighbourhood, in a home which backs onto a forest. Walking distance to a train station and a very large mall. You will have two private bedrooms, your OWN bathroom and full kitchen, 3 fireplaces, internet & HOT TUB! Separate entrance. No parties. No instant booking. We screen our guests as we live upstairs with our kids.

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.

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

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.

Waterfront Retreat | 6BR • Hot Tub • Private Beach

Create lasting memories at this Lake Simcoe family retreat. Kids will love the sandy beach, kayaks, SUP, lily pad & play area, while adults unwind in the hot tub under the stars or gather by the firepit at sunset. Inside, a lakeview kitchen opens to dining spaces for shared meals, with 3 cozy family rooms and a game room for fun. Comfortable bedrooms ensure restful nights. From summer swims to winter ice fishing, this getaway is perfect year-round for families, reunions & friends.

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)

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.