
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!

* HOT TUB* Guest Suite - Minutes to the Beach!
Welcome to the Hidden Gem - Romanic Zen Den! Your separate entrance will lead you to your lower level of the bungalow and is the perfect place to find your inner zen after enjoying the beautiful outdoors of Pickering. Elevate your experience with add-on packages! *there is another guest unit on the main floor. You will hear signs of life from above *9 pm pls no loud noise outside 4 min walk to Beach 12 min Casino 11 min Zoo 7 min Mall/Movies 18 min Thermea Spa 30 min Dwntwn Toronto

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.

Bright Private Suite w/Separate Entrance & Patio
PRIVATE Walk Out Basement Apartment W/Separate Entrance. 420 Sq.Ft space. Queen Sized Bed. Oversized Shower w/ Rainfall Shower-head. Microwave, Two Mini Fridges, Coffee/Hot Water Tea Maker. Please note: not a full kitchen. Dining/Work Table w/Benches. High Speed Wi-fi. Living Room w/ Reclining Lazy Boy Couch and 50” Smart Tv. Over 1000 Live Tv Channels and Netflix. Private Little Backyard Patio w/Table. Private Driveway ( 2 Cars). 1 Min Drive to Hwy 401. 15 Min Walk to Ajax Go Station.

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!

Toronto [45 mins] Sleep 8| Free Parking | Backyard
Why you will love your stay here: - ***ENTIRE HOME*** No one will be on the property but those on the booking. This is a DETACHED house. No connecting houses. - Open concept on the main floor so you can connect and create memories - Dedicated work from home spaces . Cat 6 ports -The 2nd floor has 4 different rooms where you can unwind and take a much deserved break - 10ft ceilings on a corner lot with lots of sunlight - Central Hub to Toronto (45 min drive)

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 • 55 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.

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

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

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

4BR Retreat with Hot Tub, Bbq and Pool Table

Home away from home with a hot tub and pool

Ravine Paradise ! heated pool and hot tub!

Lakefront House near Niagara Falls with Hot Tub!

Family Friendly | HOT TUB | Near Toronto & UOIT

Waterfront Cottage with Hot tub
Family- and pet-friendly home rentals

Deerleap Glamping Dome

Treehouse on private, isolated forest (300 acres)

Toronto Island Wonderland View

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

EXQUISITELY DECORATED, 4 Bdrm Townhome W/ Parking!

Glass Dome - Sleep Under The Stars- Free Sundays

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

Modern 4BR Home in North Oshawa
Family-friendly home rentals with a pool

The Hilton BnB Adult Luxury Suite

Stunning Skyline View Condo, Steps to CN Tower

Downtown Markham Unionville

The Penty: Luxurious Penthouse with Pool, Hot Tub

2BR Across from CN Tower & MTCC

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

Gorgeous 2BR Suite | Swimming Pool OPEN | BBQ
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £71 | £72 | £74 | £79 | £84 | £88 | £97 | £97 | £86 | £84 | £81 | £86 |
| 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!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
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- Family-friendly rentals Durham
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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
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Downsview Park
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- York University
- Toronto City Hall




