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

“Elysium” Where happiness is real!
Stay connected with our fast Bell Fibe Wi-Fi, free parking and unwind with over 1000 streaming channels on our TV, including Netflix and Prime. Whether you're here to catch the game or watch an exciting fight you’ll have everything you need for a great time Our location is the perfect base for discovering all that Pickering has to offer. You’ll be just a short drive away from fantastic restaurants, lively bars, shopping spots, and even casinos—everything you need for a fun and convenient stay!

Luxury Ground-Level "Suite Escape"
"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

Luxury Suite w/ Cafe & Sauna in Pickering
We welcome you to stay at our luxury suite that is perfect for a vacation retreat, visiting family/friends or for a business trip. Enjoy your own in-suite café, sauna, and fireplace. Our serene space will leave you relaxed from the very start to the end of your stay. There's plenty of room for yoga or stretching. Located just walking distance to Pickering’s beautiful waterfront, minutes to HWY 401, shopping, restaurants, and the GO Train Station that can take you to Downtown Toronto & more!

Brand New Private Luxury Suite Open Consept living
Sun filled Private Suite, cozy & modern. Entire space with separate entrance. Peaceful Ravine, walking path & Sunrise. Minutes to the 401 & Ajax GO Station. 18 min to Toronto Pan Am Sports Centre. Drive or GO to downtown Toronto. Walking distance to a wide variety of restaurants, major shopping plazas, Walmart, Costco, RCSS, Iqbal foods, Ajax Downs & Casino. Life Time Athletic, Ajax convention Centre. Minutes to Lake Ontario & Pickering Casino. 12 min to Dagmar Ski Resort & Whitby Thermëa spa.

Oasis near TO | Private Main Floor | Hot Tub Suite
Completely private studio suite kitchenette (no full kitchen)(no stove)(no oven) Airbnb is a separate unit with a separate entrance Exclusive hot tub access Modern space with Fireplace and 55 inch smart TV for streaming Fast Wi-Fi Approximately 30 minutes from downtown Toronto 15min to Thermea Spa, Frenchman’s Bay, Durham Live Casino, Toronto Zoo/Porsche Experience Center Parking spot for SUV size car. Trucks will not fit. Safe and secure with a disclosed exterior entrance camera

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
Contemporary 3 bed, 2 bath home w/ a European-feel. Centrally located on a low traffic court. Spacious, clean & bright! Featuring a large walk-out family room, high ceilings and wood-burning fireplace. Renovated w/ wood floors throughout. Large sunny west-facing backyard + 6 car-park on the driveway. Enjoy many unique amenities like our chromo-therapy steam room & outdoor Brazilian hammock. Walking distance to strip plaza, restaurants & parks. A comfortable home away from home!

Walk to Lake | 2BR Family Suite | Near Toronto
✨ Prime Location – 3 mins to HWY 401, Pickering GO & Town Centre 🌊 In West Shore — walk to the beach, lighthouse & Lake Ontario! Perfect for sunrise & family strolls. 🛌 Fully private walk-up basement suite — no shared spaces, clean & comfy • 2 comfortable bedrooms + spacious living room 🚗 Free parking for 2 vehicles 🍳 Full kitchen for easy meals 👨👩👦 Ideal for families & travelers exploring Toronto 🌟 Enjoy complete privacy, comfort & beachside vibes in Pickering!

Muskoka on the City
Located in Rouge National Urban Park, steps from a beautiful lake and beach(Note:beach was temporarily closed by government now).Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Private Sauna Suite Retreat
1 Bedroom • 1.5 Bathrooms • Private Entire Unit Newly renovated and quiet, just minutes from Hwy 401 and local restaurants. Highlights • Private self check-in • Driveway parking for 1 car • Private sauna • 65 Inch TV with Netflix Amenities Fresh towels, linens, tooth brushes & pastes, hairdryer, home essentials, shower essentials, and extra pillows/towels on request. Spotless home, quick replies, and your comfort guaranteed - book with confidence.

Lower Unit - Central location
Enjoy the charming touches of this cozy basement suite with a clean modern feel. Beautifully decorated featuring a spacious open concept living room/kitchen combo area with spacious island and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is bright and full of warmth. Conveniently located: 5 min walk to Pickering Town Center, 10 min walk to the Pickering GO and 2 min drive to 401.

Ultra-Modern Luxury Retreat! Close to Thermea SPA.
COZY and INVITING, this modern suite is in a quiet, family-friendly Ajax neighborhood. Just 10 minutes to Thermea Spa and Ajax GO Station, and a short walk to parks, shops, and groceries. Newly built with deluxe finishes, the 1,000 sq. ft. space includes in-floor heating, an electric fireplace, a spacious sofa, and smart TV with Netflix/Prime. Downtown Toronto is 35–45 mins by car, and Pearson Airport or Mississauga in about 55 mins.

Serene Stays - Pickering (5Beds, 2.5Baths, 4Park)
Welcome to Serene Stays - Pickering, where you'll find comfort, style, and convenience all come together! This is a newly built, spacious 4 bedroom, 2 storey home where you can completely relax with access to the entire home - boasting 4 bedrooms, 2.5 bathrooms, living room, dining room, full kitchen, private outdoor patio, and laundry room. This home has 4 parking spaces and is perfect for large families or groups!
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

4BR Escape with HotTub, Bbq & PoolTable

“Lakeside Dreams”: All season HotTub w/lake views

Backyard Oasis | Hot Tub & Playground

Home away from home with a hot tub and pool

Downtown Markham Unionville

The Penty: Luxurious Penthouse with Pool, Hot Tub

Stylish Condo | Walk to BMO Field + FIFA Festivals

Large Luxury Villa with Swim Spa! Near downtown!
Family- and pet-friendly home rentals

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Rustic Ridge

Large house 3 bed 2 bath 2 parkings

Treehouse on private, isolated forest (300 acres)

Toronto Island Wonderland View

SNAKE CABIN(rustic, 'off-the-grid')

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

NEWLY RENOVATED, 3 Bdrm Modern Oasis W/ Parking!!!
Family-friendly home rentals with a pool

Pool Now Open | Executive Suite | 3PM checkout

The Hilton BnB Adult Luxury Suite

Luxury CN Tower and Lake View Penthouse Sleeps 10

Stunning Skyline View Condo, Steps to CN Tower

Four season glamping dome under the stars

Bright and Airy Guest Suite with Pool

Luxury Stay w/phenomenal view!

2BR Across from CN Tower & MTCC
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £78 | £78 | £83 | £80 | £85 | £88 | £97 | £97 | £87 | £85 | £82 | £87 |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Pickering

Total holiday rentals
Explore 690 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 17,950 verified reviews to help you choose

Pet-friendly holiday rentals
Find 180 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
440 properties have a dedicated workspace

Wifi availability
680 of Pickering holiday rentals include wifi access

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

4.8 Average rating
Pickering stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with a hot tub Pickering
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- Rentals with a patio Pickering
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Distillery District
- Toronto Eaton Centre
- Exhibition Place
- Downsview Park
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Casa Loma
- Massey Hall
- Scarborough Town Center
- York University
- Dufferin Grove Park
- Lakeridge Ski Resort





