
Family-friendly vacation 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!

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
Welcome! Our 3 bedroom, 2 bath home is centrally located on a low traffic court. Spacious, clean and bright! Featuring a large walk-out family room with high ceilings and a wood-burning fireplace. Completely renovated with wood floors throughout. Large sunny west-facing backyard and 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!

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt
Spacious lower-level legal basement apartment featuring open-concept living room & kitchen. 2 queen-sized beds & 1 sofa bed. Located near the 401, grocery stores, restaurants, malls, casinos, parks, Toronto Zoo & 5-minute drive to the GO Train. 1 vehicle parking. Electric car charging $10/day Extra guests $25/day. Private side entrance for self-check in with access code. ✅ Wi-Fi, iMac & Printer ✅ TV Box with Netflix/Amazon Prime ✅Variety of Board Games ✅ Full Kitchen w/condiments

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!

4BR |Chef Kitchen| Casino Dagmar Thermea (15km)
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!

RedDore - 2 Bedroom Cozy Basement Suite
Enjoy the charming touches of this spacious basement suite with a clean modern feel. Beautifully decorated featuring a spacious living/dining room combo area, and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is luxurious and full of warmth. Along with our beautiful accomodations we have car rentals available to make your trip complete. Just ask for details.
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

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

Home away from home with a hot tub and pool

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub

The Fort York Flat

Family Friendly | HOT TUB | Near Toronto & UOIT

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

Large & Bright 2BR+Den in Midtown w/ Free Parking

South Geodome - Birchwood Luxury Camping
Family- and pet-friendly home rentals

Modern Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard

*BRAND NEW*Perfect 4 BR Townhouse Markham *Sleep 8

Luxurious Spacious Dream Home with Parking!

Entire Home Steps from Beach-prestigious location

EXQUISITELY DECORATED, 4 Bdrm Townhome W/ Parking!

Cyberspace - no cleaning fees, New Private Hot Tub

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

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

Private Walkout Suite | 3 PM Checkout | 1.5G Wifi

The Hilton BnB Adult Luxury Suite

Treehouse on private, isolated forest (300 acres)

The Penty: Luxurious Penthouse with Pool, Hot Tub

The Farmer's Cottage

Hidden gem in Humber bay shores Toronto w/ parking

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,293 GYD | G$20,502 GYD | G$20,920 GYD | G$22,385 GYD | G$23,849 GYD | G$24,895 GYD | G$27,406 GYD | G$27,406 GYD | G$24,477 GYD | G$23,849 GYD | G$23,012 GYD | G$24,477 GYD |
| 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 vacation rentals that are family-friendly in Pickering

Total vacation rentals
Explore 650 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at G$4,184 GYD per night before taxes and fees

Verified guest reviews
Over 17,640 verified reviews to help you choose

Pet-friendly vacation rentals
Find 170 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
430 properties have a dedicated workspace

Wi-Fi availability
650 of Pickering vacation rentals include wi-fi access

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

4.7 Average rating
Pickering stays receive an average rating of 4.7 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- BMO Field
- Distillery District
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Lakeridge Ski Resort
- Dufferin Grove Park
- Downsview Park
- Toronto City Hall
- Christie Pits Park




