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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.

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Top guest favourite
A modern kitchenette is shown, featuring a silver refrigerator and a stainless-steel microwave above the stove. Light cabinetry contrasts with a wood countertop. A gray sofa sits in the foreground, accompanied by a wall clock and a lamp, enhancing the sleek and organized space.
Apartment in Pickering
4.94 out of 5 average rating, 345 reviews

“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!

Top guest favourite
A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.
Guest suite in Pickering
4.88 out of 5 average rating, 739 reviews

* 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

Guest favourite
The spacious living area features a leather sectional sofa and a cozy ottoman, situated atop a soft area rug. A modern kitchen with an island and dark cabinetry is visible in the background, complemented by ambient blue lighting.
Guest suite in Ajax
4.99 out of 5 average rating, 148 reviews

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.

Guest favourite
Guest suite in Pickering
4.91 out of 5 average rating, 262 reviews

Urban HotTub Oasis/Separate Entrance/Unit/DT 30min

Completely private studio suite kitchenette (no full kitchen) Exclusive hot tub access for ultimate relaxation Modern space with Fireplace and smart TV for streaming Fast Wi-Fi and dedicated parking included Approximately 30 minutes from downtown Toronto Conveniently located near Thermea Spa and Frenchman’s Bay, Pickering Casino Resort & Toronto Zoo One parking spot for SUV size car or smaller. Trucks will not fit. Safe and secure with a disclosed entrance camera and responsive hosting

Top guest favourite
A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.
Home in Pickering
4.84 out of 5 average rating, 116 reviews

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!

Guest favourite
A well-maintained exterior of a single-story brick residence is highlighted, featuring a manicured lawn and vibrant flowerpots along the entrance. A vehicle is parked in the driveway, and decorative accents add a welcoming touch to the home.
Flat in Donevan
4.93 out of 5 average rating, 855 reviews

Just like home

This is an fully furnished basement apartment Quiet neighborhood close to bus stop, shopping and restaurants. Ten minute drive to Oshawa Center and downtown Oshawa. Reserve parking in driveway on left side. Breakfast ingredients are included; Eggs, Waffles, Cereal ,Toast, Coffee , Tea and etc. Our guests can rest assured that the bedding is washed and changed with each and every new guest, and for those who stay for a week or more , bedding is changed every five days or upon request.

Top guest favourite
A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.
Farm stay in Uxbridge
4.98 out of 5 average rating, 250 reviews

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.

Guest favourite
A bright living area features a neutral-toned sofa positioned across from a wooden coffee table adorned with a small vase of colorful flowers. A wall art piece of abstract design adds visual interest. The open layout includes doorways leading to the kitchen and bedrooms.
Home in Pickering
4.86 out of 5 average rating, 150 reviews

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!

Top guest favourite
The living room features a large sectional sofa and a coffee table with a decorative plant. A modern gas fireplace is situated beneath a wall-mounted television displaying a streaming service. Sunlight fills the space through multiple windows, creating a bright and cozy atmosphere.
Home in Pickering
4.98 out of 5 average rating, 131 reviews

Chefs Kitchen I TorontoZoo I 8km to EV Chrg I Park

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)

Superhost
A modern living area features a gray sectional sofa and two light-colored chairs positioned around a glass coffee table. A wall-mounted television is situated above a contemporary electric fireplace, with a decorative plant adding a touch of greenery to the space.
Guest suite in Whitby
4.81 out of 5 average rating, 128 reviews

Luxury 2 Bedroom Apartment - 5 mins to Thermea Spa

★ "Very nice apartment! Clean, spacious, and modern'' ★ ☞ Fully Private unit!!! ☞ Fully equipped kitchen!!!! With all required machines and pots ☞ Extended Kitchen Island ☞ All rooms w/ queen + Sheets and Duvet !!!!!! ☞ 55” smart Samsung TV w/ Netflix + Samsung sound bar with Sub ☞ Central AC + Heating ☞ Onsite washer + dryer ☞ Parking → 1 on the driveway!!!! ☞ 700mbps wifi ☞ Open Concept 5 mins → Thermëa spa village 12 mins → Whitby and Ajax GO Station

Guest favourite
A cozy living area is presented with a grey sofa adorned with yellow cushions. A large TV is mounted on the wall, facing a white coffee table on a textured rug. A colorful abstract painting decorates one wall, complemented by a small indoor plant.
Flat in Pickering
4.92 out of 5 average rating, 212 reviews

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.

Guest favourite
A modern living space features a comfortable gray couch and two stylish lamps on side tables. A coffee table sits at the center, with a small dining area visible in the background. Natural light enters through large windows, enhancing the warm ambiance.
Guest suite in Ajax
4.77 out of 5 average rating, 123 reviews

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.

Popular amenities for Pickering family-friendly rentals

When is the best time to visit Pickering?

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Quick stats about holiday rentals that are family-friendly in Pickering

  • Total holiday rentals

    Explore 620 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 17,490 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    400 properties have a dedicated workspace

  • Wifi availability

    610 of Pickering holiday rentals include wifi 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

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