Family-friendly holiday rentals in Pickering

4.93 out of 5 average rating, 434 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!

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.

4.92 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.

4.96 out of 5 average rating, 123 reviews

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

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.

4.9 out of 5 average rating, 335 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

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.

4.86 out of 5 average rating, 131 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!

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.

4.92 out of 5 average rating, 108 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!!

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, 163 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)

4.86 out of 5 average rating, 132 reviews

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.

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.

4.78 out of 5 average rating, 236 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!

4.99 out of 5 average rating, 189 reviews

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

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.

4.93 out of 5 average rating, 247 reviews

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

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.

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.