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.
Condo in Pickering
4.93 out of 5 average rating, 337 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
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, 146 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. 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

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
4.87 out of 5 average rating, 734 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

Top Guest favourite
A cozy living area is presented, featuring a large comfortable couch and a wooden coffee table. A television stands atop a media console, with a decorative plant placed on the table. The space is illuminated by natural light streaming through glass doors, leading to the outdoor patio.
Guest suite in Ajax
4.96 out of 5 average rating, 531 reviews

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.

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, 114 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!

Superhost
A cozy living space features a modern television stand with a flat-screen TV, accentuated by a bold artwork. A gray couch with yellow cushions invites relaxation, complemented by a light rug atop wooden flooring. Large windows allow natural light to brighten the room.
Home in Ajax
4.85 out of 5 average rating, 213 reviews

Moons & Noons -Separate Unit for your Comfort

Welcome to our charming retreat in Ajax! You'll be greeted by living space adorned with carefully curated decor. The sofa beckons you to unwind, while the large windows' scenic views allow natural light to fill the room. Just take a stair down to the Basement, to be greeted by an elegant kitchenette. Enjoy a drink on the sofa while watching shows on 55' QLED. Step into a world of relaxation in our stunning bathroom designed to calm your stress. Your unforgettable stay awaits U!

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, 149 reviews

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

Guest favourite
Guest suite in Pickering
4.91 out of 5 average rating, 258 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. Safe and secure with a disclosed entrance camera and responsive hosting

Guest favourite
A welcoming home features a well-maintained exterior surrounded by lush green trees. The entrance is adorned with a small balcony and pathway, inviting guests into a bright living space. The design balances modern elements with natural landscaping, creating an inviting first impression.
Apartment in Pickering
4.82 out of 5 average rating, 121 reviews

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.

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.
Apartment in Pickering
4.93 out of 5 average rating, 210 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.

Top Guest favourite
The living area features a spacious couch and two cozy blue accent chairs, positioned around a round coffee table. A large flat-screen TV is mounted on the wall, while a modern mirror reflects the open concept layout, enhancing the light from the recessed lighting.
Home in Ajax
5 out of 5 average rating, 121 reviews

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.

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, 120 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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Avg. price$172 NZD$174 NZD$178 NZD$190 NZD$203 NZD$211 NZD$233 NZD$233 NZD$208 NZD$196 NZD$196 NZD$194 NZD
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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 $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 17,490 verified reviews to help you choose

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    610 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

Destinations to explore

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