Family-friendly holiday rentals in Pickering

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 690 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 17,950 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 180 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    440 properties have a dedicated workspace

  • Wifi availability

    680 of Pickering holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pickering rentals

  • 4.8 Average rating

    Pickering stays are highly rated by guests – averaging 4.8 out of 5!

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
Home in Pickering
4.93 out of 5 average rating, 431 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!

Guest favourite
A cozy living area features a light-colored sofa adorned with pillows, paired with a simple coffee table. A dining table is positioned in the background. Natural light flows through the elegant window treatments, contributing to a bright and inviting space.
Guest suite in Pickering
4.92 out of 5 average rating, 167 reviews

Separate 2 Bedroom & 2 Washroom up to 4 people.

Hotel-style apartment in a home annex. Not a basement. The apartment has 2 bedrooms with attached washrooms, Living area, kitchen, dining. Our property accommodates up to 4 people. Children are welcome to stay. Conveniently located just off Highway 401. Close to downtown Pickering, Go Station, mall, restaurants. We are a good stopover point if you are traveling to downtown Toronto which is only a 40 min drive. Note: Show us your ID when "Checking In" and it has to match with your booking name.

Top guest favourite
A modern living space is highlighted by a spacious bed and an entertainment area featuring a large wall-mounted TV. A cozy seating arrangement includes a soft couch and a stylish armchair. Ambient lighting is provided by a chandelier above, complemented by a decorative fire feature.
Guest house in Pickering
4.96 out of 5 average rating, 123 reviews

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.

Top guest favourite
The living room features two couches, one convertible into a bed, surrounding a coffee table. A fireplace is situated to the left, with a stack of wood beside it. A wall-mounted TV is visible, enhancing the space's functionality for relaxation and entertainment.
Guest suite in Pickering
4.97 out of 5 average rating, 116 reviews

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!

Guest favourite
Guest suite in Pickering
4.9 out of 5 average rating, 330 reviews

Hot Tub Oasis | 35 Min to DT | Main Floor Suite

Completely private studio suite kitchenette (no full kitchen)(no stove)(no oven) Airbnb is a separate unit with a separate entrance Exclusive hot tub access Modern space with Fireplace and 55 inch smart TV for streaming Fast Wi-Fi Approximately 30 minutes from downtown Toronto 15min to Thermea Spa, Frenchman’s Bay, Durham Live Casino, Toronto Zoo/Porsche Experience Center Parking spot for SUV size car. Trucks will not fit. Safe and secure with a disclosed exterior entrance camera

Top guest favourite
Guest suite in Ajax
4.96 out of 5 average rating, 585 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.

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
4.86 out of 5 average rating, 130 reviews

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

Contemporary 3 bed, 2 bath home w/ a European-feel. Centrally located on a low traffic court. Spacious, clean & bright! Featuring a large walk-out family room, high ceilings and wood-burning fireplace. Renovated w/ wood floors throughout. Large sunny west-facing backyard + 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!

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
4.99 out of 5 average rating, 162 reviews

Toronto [45 mins] Sleep 8| Free Parking | Backyard

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 serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.
Guest suite in Pickering
4.78 out of 5 average rating, 235 reviews

Muskoka on the City

Located in Rouge National Urban Park, steps from a beautiful lake and beach(Note:beach was temporarily closed by government now).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!

Top guest favourite
A cozy bedroom features a spacious bed with elegant bedding, flanked by two nightstands. A dresser is positioned against the wall, and natural light filters through a window, illuminating the soft grey walls and light-colored flooring.
Home in Ajax
4.99 out of 5 average rating, 186 reviews

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 • 65 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.

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
4.93 out of 5 average rating, 246 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 spacious living area features a large sectional sofa paired with a modern armchair. Natural light streams through the expansive windows, highlighting a round coffee table and a light-toned area rug underneath. A potted plant adds a touch of greenery to the serene space.
Home in Pickering
4.88 out of 5 average rating, 144 reviews

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!

Popular amenities for Pickering family-friendly rentals

When is the best time to visit Pickering?

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Avg. price$136 SGD$136 SGD$143 SGD$138 SGD$147 SGD$154 SGD$169 SGD$169 SGD$151 SGD$147 SGD$142 SGD$151 SGD
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Destinations to explore

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