Family-friendly holiday rentals in Pickering

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.

4.88 out of 5 average rating, 827 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

Indoor spacesKitchenHot tub

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.

4.91 out of 5 average rating, 173 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.

FamilyKitchenAccess

4.94 out of 5 average rating, 109 reviews

A spacious back deck features a hot tub and seating area, surrounded by greenery. Large glass doors provide a view into the living room, while a cooking area and dining table are positioned outdoors. A metal container holds beverages, inviting relaxation.

Home in Ajax

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Bring your family or team together in this luxurious home! Beautifully refurnished in 2022, including a new hot tub and new hotel-quality mattresses & linens, this 4000 sq. ft house is ideally suited for large families or athletic teams. Featuring a remodeled kitchen w/ gas stove, 7 new beds (3 king), gym, office, smart TVs, 4 parking spaces & fast Wi-Fi. Only 5 minutes from the 401 & Ajax Go Train station, accessing the city is a breeze. Tennis + playground 50 meters away. *3 extra beds avail

Indoor spacesKitchenNearby

4.85 out of 5 average rating, 107 reviews

Luxury & Stylish 3BD | Chefs Kitchen & Cozy

Discover the charm of our inviting 3-bedroom house in the heart of Pickering's family friendly neighbourhood, West Shore. Featuring a newly renovated luxurious chef's kitchen, comfortable living space, and a tranquil layout, our home offers the perfect blend of relaxation and convenience. With Frenchman's Bay just minutes away, you'll have easy access to the best of the beautiful lake. Convenient Location - Minutes to Go Station, Pickering Town Centre and HWY 401! 25 Min. to UNION STN Via GO

KitchenFamilyNearby

A cozy living area is presented with a light-colored couch adorned with throw pillows, facing a circular coffee table. Two armchairs are placed on a soft area rug. An accent mirror reflects the space, while a plant adds a touch of greenery to the corner.

4.81 out of 5 average rating, 137 reviews

Family Friendly Basement with Separate Entrance!

Open concept basement apartment (No walls separating rooms) 1 Queen bed and a Futon folds out into a Double bed . Accommodates Family of 4, NOT 4 Adults (2Adults/2children) . Separate entrance/ONE prkg spot. Located in a quiet neighbourhood in Pickering. Family friendly, NO parties/gatherings. Close to 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. PLEASE read ALL house rules prior to booking.

Indoor spacesFamilyAccuracy

4.94 out of 5 average rating, 209 reviews

A comfortable sofa in a neutral brown tone is positioned in the living room, complemented by a decorative blanket. In the background, a modern kitchen with bar stools and a light-colored counter is visible, along with a window allowing natural light into the space.

Flat in Pickering

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

Legal lower-level basement apartment with kitchen and living room. Sleeps up to 6 guests with 2 queen beds and 1 sofa bed. Close to Hwy 401, restaurants, shopping, parks, Toronto Zoo, and GO Train. 🚗 *1 PARKING SPOT ONLY*. Additional vehicles may apply directly to the City of Pickering's Parking Consideration Program, subject to City approval. Any parking tickets or fines are the guest's responsibility. 👥 Extra Guests: $25/day 🌳 No smoking in/out of the property. 🔑 Private entrance

Indoor spacesKitchenCheck-in

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.

4.87 out of 5 average rating, 142 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!

Indoor spacesFamilyQuiet

Superhost

A cozy living area features two comfortable seating options, each with decorative pillows. A small coffee table is positioned between them. In the background, the kitchen area is visible, showcasing modern cabinetry and appliances. Soft lighting accentuates the warm tones of the furnishings.

4.85 out of 5 average rating, 130 reviews

Sleep 6+ Free parking- 2bds- 1bath No pets/smoke

Enjoy this newly renovated separate unit with privacy and security. 2 bedrooms! 1 bathrooms. This place can hold 6 people.2 single mattress/foam for the 7 &8 guest. Great for people who are visiting the city and ready to explore Toronto and GTA. This place is walking distance from local restaurants to buffets, bars, parks and Multicultural restaurants. This street has safety, family privacy and lots of room for parking. Smoke free and pet free. Bring your own towels!!

FamilyKitchenHospitality

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.

4.99 out of 5 average rating, 172 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)

FamilyIndoor spacesCleanliness

Superhost

The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.

Dome in Uxbridge

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

FamilyKitchenCheckout

4.86 out of 5 average rating, 158 reviews

4.84 out of 5 average rating, 191 reviews

Walk to Lake | 2BR Family Suite | Near Toronto

✨Prime Location—3 mins to HWY 401 & GO Station 🌊West Shore—walk to beach & Lake Ontario 🏡Fully private walk-up basement suite with its own exclusive entrance, full kitchen & bath. NO SHARED INDOOR SPACES！ (Note: This rental unit is only included the entire Basement area. Ground/Second Floors are for host only which not included.) 🛏️2 Comfy bedrooms + spacious living room 🚗Free parking for 2 vehicles 👥Ideal for families & travellers

KitchenFamilyHeating

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.