
Family-friendly vacation rentals in Pickering
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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!

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. 30 min 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 village

Spacious Basement with Separate Entrance!
Open concept basement apartment (No walls separating rooms) 1 Queen bed and a couch folds out into a Double bed (Futon). **Accommodates Family of 4, NOT 4 Adults. Separate entrance with ONE prkg spot. Located in a prestigious, quiet, neighborhood in Pickering that borders Toronto. Walking distance from Rouge National Urban Park, Hiking Trails, plaza, and public Transit. 5 minutes drive from U Of T (Scarborough) Close to Toronto Zoo, PanAm Center, Go Stn and Hwy- 30 mins to Downtown Toronto

* 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

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.
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!

Lakeside Sweet Home
Private entrance with passcode keypad self check-in 10-MINUTES WALK to BEACH !!! 2 bedrooms, Queen-sized+Full-sized bed and a Sofa bed in the living room 30-sec walk to Bus stop 4-min drive to Pickering Go station 3-min drive to reach Hwy 401 8-min drive Toronto Zoo 30-min drive Toronto City Center 40-inch TV with smart TV box Free Washer and Dryer in the suite Fully equipped Kitchen. Coffee maker,stove,oven,microwave, and refrigerator, toaster, cookware and dishes

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.

Adorable 1-bedroom with free parking on premises
Forget your worries in this spacious and serene space. Enjoy this cozy, modern guest suite with a private bathroom, kitchen, workspace, HD TV with alexa fire stick Amazon Prime and fast wifi. Perfect getaway, 5 minutes walk to Ajax Waterfront Park and close to Casino Ajax, Rotary Park and general hospital. Note that this is a guest suite as a part of the main house where the landlord and their family live.

Muskoka on the City
Located in Rouge National Urban Park, steps from a beautiful lake and beach. 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!
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

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

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

The Penty: Luxurious Penthouse with Pool, Hot Tub

The Fort York Flat

Luxury Stay w/phenomenal view!

Luxur condo in downtown Mississauga

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

Cyberspace - no cleaning fees, New Private Hot Tub
Family- and pet-friendly home rentals

Private 1BR Condo w/Kitchen

GTA Suite | Lakeridge Ski Resort | Pickering GO

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

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

Spacious Guest Room close to 401

Mackenzie Cottage

Private 1-br Apartment: Your Secluded Getaway!

Quiet oasis minutes from Toronto
Family-friendly home rentals with a pool

The Hilton BnB Adult Luxury Suite

Treehouse on private, isolated forest (300 acres)

Backs onto nature near IBM and Hospital

Bright, spacious luxury basement apartment

Hidden gem in Humber bay shores Toronto w/ parking

Condo in Heart of Mississauga

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Private 2-Bdrm Hideaway with Parking
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,308 GYD | G$20,517 GYD | G$20,936 GYD | G$22,401 GYD | G$23,867 GYD | G$24,914 GYD | G$26,798 GYD | G$26,798 GYD | G$24,495 GYD | G$23,029 GYD | G$23,029 GYD | G$22,820 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$2,094 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
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Toronto City Hall
- Christie Pits Park
- Royal Woodbine Golf Club