
Family-friendly holiday rentals in Pickering
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Pickering

Total holiday rentals
Explore 680 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 18,900 verified reviews to help you choose

Pet-friendly accommodation
Find 190 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
440 properties have a dedicated workspace

Wi-Fi availability
670 of Pickering holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Pickering rentals

4.7 Average rating
Pickering stays receive an average rating of 4.7 out of 5 from guests
Top-rated family-friendly rentals in Pickering
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

* 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

“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 & Stylish 3BD | Chefs Kitchen & Cozy
Discover the charm of our inviting 3-bedroom house in the heart of Pickering's family friendly neighbourhood, West Shore. Featuring a newly renovated luxurious chef's kitchen, comfortable living space, and a tranquil layout, our home offers the perfect blend of relaxation and convenience. With Frenchman's Bay just minutes away, you'll have easy access to the best of the beautiful lake. Convenient Location - Minutes to Go Station, Pickering Town Centre and HWY 401! 25 Min. to UNION STN Via GO

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt
Legal lower-level basement apartment with kitchen and living room. Sleeps up to 6 guests with 2 queen beds and 1 sofa bed. Close to Hwy 401, restaurants, shopping, parks, Toronto Zoo, and GO Train. 🚗 *1 PARKING SPOT ONLY*. Additional vehicles may apply directly to the City of Pickering's Parking Consideration Program, subject to City approval. Any parking tickets or fines are the guest's responsibility. 👥 Extra Guests: $25/day 🌳 No smoking in/out of the property. 🔑 Private entrance

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!

Modern 4beds+Office: Whole house with 4/5 parking
Welcome to our charming retreat nestled in the heart of Pickering. This cozy 4-bed house offers a serene escape from the busy Toronto city while staying conveniently close to all its attractions. Step inside to a state-of-the-art furnished living space. Modern kitchen and vibrant dining. 4 bedrooms 2.5 baths 1 dedicated office 2 balconies for patio space 2 free driveway parking Ideal for families, friends and working professionals seeking comfort and urban living at its finest.

Sleep 6+ Free parking- 2bds- 1bath No pets/smoke
Enjoy this newly renovated separate unit with privacy and security. 2 bedrooms! 1 bathrooms. This place can hold 6 people.2 single mattress/foam for the 7 &8 guest. Great for people who are visiting the city and ready to explore Toronto and GTA. This place is walking distance from local restaurants to buffets, bars, parks and Multicultural restaurants. This street has safety, family privacy and lots of room for parking. Smoke free and pet free. Bring your own towels!!

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)

Walk to Lake | 2BR Family Suite | Near Toronto
✨Prime Location—3 mins to HWY 401 & GO Station 🌊West Shore—walk to beach & Lake Ontario 🏡Fully private walk-up basement suite with its own exclusive entrance, full kitchen & bath. NO SHARED INDOOR SPACES! (Note: This rental unit is only included the entire Basement area. Ground/Second Floors are for host only which not included.) 🛏️2 Comfy bedrooms + spacious living room 🚗Free parking for 2 vehicles 👥Ideal for families & travellers

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!

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.
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Hot Tub Oasis | 35 Min to DT | Main Floor Suite

The Bubble Glamping Dome

Ravine Paradise ! heated pool and hot tub!

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Home away from home with a hot tub and pool

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

Summer Getaway with HotTub, PoolTable • Sleeps 10+
Family- and pet-friendly home rentals

Serene Stays - Pickering (5Beds, 2.5Baths, 4Park)

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

Modern 4BR Home in North Oshawa

Rouge Basement · Sleeps 6 & Free Parking

EXQUISITELY DECORATED, 4 Bdrm Townhome W/ Parking!

Treehouse on private, isolated forest (300 acres)

Deerleap Glamping Dome

Large house 3 bed 2 bath 2 parkings
Family-friendly home rentals with a pool

Toronto Vacation | ➊ The One Toronto Villa

Four season glamping dome under the stars

The Ridge Roost - Uxbridge Township

Toronto Pool Retreat

1BR Bluffs | Pool + Yard | Pets Ok | EV Charger

New Custom-Built | Marble Pool + BBQ | Toronto

The Hilton BnB Adult Luxury Suite

Luxurious 2 bdr suite near SQ1, UTM, parking/pool
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $146 AUD | $146 AUD | $154 AUD | $157 AUD | $171 AUD | $185 AUD | $182 AUD | $182 AUD | $162 AUD | $158 AUD | $153 AUD | $162 AUD |
| 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 |
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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Coca Cola Coliseum
- Massey Hall
- Enercare Centre
- Vaughan Mills





