
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.

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.

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.

Entire Suite : Private Place in Pickering Village
Absolutely NO Party or Event Quiet and safe neighborhood . spacious and comfortable above Ground walk-out basement ,bright with lots of natural sunlight. Just east of Toronto , about 40 minutes to DT Toronto by car. Separate entrance, have the whole walkout basement to you. private bathroom and open concept area with large living room, dining room & kitchen . Just minutes ( by car) to the Highway 401, Pickering Go station . Walmart Pickering supercenter about 5 mins away .

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!

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.

Peaceful & Private Karma Stay, Easy Toronto Access
Relax in the spacious, newly renovated basement with a separate entrance. As hosts, we take pride in being approachable and friendly. Having spent our own fair share of time away from home since a young age & exploring different places, we deeply understand the importance of providing a warm & peaceful environment for our guests. Your comfort and well-being are our top priorities, and we're here to ensure your stay feels like a welcoming home.

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

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

Beautiful Penthouse with Breathtaking View

Year-Round Heated Pool & Hot Tub Family Oasis

The Fort York Flat

Luxury Stay w/phenomenal view!

Large Luxury Villa with Swim Spa! Near downtown!

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

Modern Executive Townhome w/ Rooftop Hot Tub Oasis
Family- and pet-friendly home rentals

GTA Suite | Lakeridge Ski Resort | Pickering GO

Private Lower 1 BR + Sofabed Self Checkin with PKG

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

Spacious 2BD 3-6 ppl homestyle BSMT mansion with window basement 130sqm

The Cozy Cove Studio

Mackenzie Cottage

Orchard cottage, experience the farm in the city

Airbnb King & Queen/Wifi/ near Toronto & Casino
Family-friendly home rentals with a pool

The King's Rest

The Hilton BnB Adult Luxury Suite

Treehouse on private, isolated forest (300 acres)

The Penty: Luxurious Penthouse with Pool, Hot Tub

Ravine Paradise ! heated pool and hot tub!

Toronto's Perfect View Apartment

Bright, spacious luxury basement apartment

Condo in Heart of Mississauga
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,269 GYD | G$20,478 GYD | G$20,896 GYD | G$22,359 GYD | G$23,821 GYD | G$24,866 GYD | G$27,374 GYD | G$27,374 GYD | G$24,448 GYD | G$22,986 GYD | G$22,986 GYD | G$22,777 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 620 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at G$2,090 GYD per night before taxes and fees

Verified guest reviews
Over 17,490 verified reviews to help you choose

Pet-friendly vacation rentals
Find 160 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
400 properties have a dedicated workspace

Wi-Fi availability
610 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
Destinations to explore
- Montreal Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Mount Pocono Vacation rentals
- Capital District, New York Vacation rentals
- Grand River Vacation rentals
- Island of Montreal Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Rentals with lake access Pickering
- Rentals with an EV charger Pickering
- Rentals with a fireplace Pickering
- Apartment rentals Pickering
- Waterfront rentals Pickering
- Rentals with a washer and dryer Pickering
- Rentals with breakfast Pickering
- Condo rentals Pickering
- Cottage rentals Pickering
- Townhouse rentals Pickering
- Rentals with outdoor seating Pickering
- Guesthouse rentals Pickering
- Private suite rentals Pickering
- House rentals Pickering
- Rentals with a hot tub Pickering
- Rentals with pools Pickering
- Beachfront rentals Pickering
- Smoking-friendly rentals Pickering
- Rentals with a fire pit Pickering
- Rentals with a patio Pickering
- Rentals with beach access Pickering
- Pet-friendly rentals Pickering
- Fitness-friendly rentals Pickering
- Family-friendly rentals Durham Region
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Toronto City Hall
- Rouge National Urban Park
- Christie Pits Park
- Royal Ontario Museum
- Royal Woodbine Golf Club
- Nathan Phillips Square




