Compare Vacation Rentals & Airbnb in Pickering

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Pickering vacation rentals
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1167 Rentals and Airbnb in Pickering

Best family friendly Pickering vacation rentals

Among the 1167 accommodations in Pickering, here are the 4 best family friendly rentals

King Bed, 3 Tvs, Fifa Sports Channels And More… - Pickering
Pickering
22/08 – 02/09
$717/nighttotal: $7887 (11 )

King Bed, 3 Tvs, Fifa Sports Channels And More…

4 4
house , Toronto
This spacious 3-bedroom detached house in Ajax, Canada, offers convenient access to major routes and public transport, situated approximately 35 kilometres east of Toronto and close to natural attractions such as Durham Regional Forest and Ajax Waterfront Park.
This pet-friendly property provides 232 square metres of living space, accommodating up to six guests with three bedrooms, two bathrooms, a fully equipped kitchen, a garden, a patio, and free parking, making it ideal for families visiting the Toronto area.
Luxury & Stylish 3bd | Chefs Kitchen & Cozy - Pickering
9.7 91 reviews
Pickering
12/07 – 31/07
$420/nighttotal: $7980 (19 )

Luxury & Stylish 3bd | Chefs Kitchen & Cozy

1 6
apartment , Toronto
This three-bedroom house, situated in Pickering's West Shore neighbourhood, is conveniently located approximately 4.8km from Pickering GO station, Pickering Town Centre, and Highway 401, offering easy access to Toronto Union Station via a 23-minute GO Train journey.
The property boasts a newly renovated chef's kitchen with stainless steel appliances, including a Wolf cooktop, two modern bathrooms, a large smart TV, keyless entry, and two dedicated parking spaces; sleeping six guests comfortably, it's close to Frenchman's Bay for waterside activities.
Prime Location! Peaceful Country Living With Modern Comfort & City Convenience ! - Pickering
10 2 reviews
Pickering
10/10 – 16/10
$378/nighttotal: $2268 (6 )

Prime Location! Peaceful Country Living With Modern Comfort & City Convenience !

4 5
apartment , Oshawa
This family-friendly bungalow, offering 186 square meters of living space, is situated on Taunton Road in Ajax, providing convenient access to major routes and attractions such as Thermea Spa, Pickering Casino, and the Toronto Zoo, and is also near Rouge National Urban Park and Milne Dam Conservation Park. This property accommodates up to 9 guests with 4 bedrooms and features a fully equipped entertainment basement complete with a pool table, ping pong table, home theatre, and workout equipment, alongside a spacious garden and parking.
167 M² House ∙ 4 Bedrooms ∙ 8 Guests - Pickering
Pickering
10/10 – 16/10
$288/nighttotal: $1728 (6 )

167 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 5
house , Toronto
This modern four-bedroom detached house is situated in Ajax, a short walk from Lake Ontario and its waterfront trail, offering convenient access to major retailers and the Ajax GO Station, which is approximately 3 kilometres away.
This family-friendly property provides accommodation for eight guests across 166 square metres, featuring a main-floor bedroom with a bathroom, an open-concept living space, a balcony with potential lake views, and parking for two vehicles, all within a 5-minute drive of the Ajax Convention Centre and an 8-minute drive of Pickering Casino Resort.

Best Pickering vacation rentals with parking

Upscale Pickering Escape | Near Lake & Dining - Pickering
Pickering
20/06 – 27/06
$1202/nighttotal: $8414 (7 )

Upscale Pickering Escape | Near Lake & Dining

5 2
apartment , Toronto
This five-bedroom, five-bathroom property in Pickering, Ontario, is situated a short 1.8km walk from Lake Ontario and 1.6km from Millennium Square.
The self-catering apartment sleeps ten guests and boasts a fully equipped kitchen, in-unit laundry, parking, air conditioning, Wi-Fi, and a fireplace; nearby attractions include Cineplex Pickering cinemas, Scarborough Golf and Country Club, Toronto Zoo, and Veterans' Point Gardens.
Vacation Home In Pickering - Pickering
9.8 161 reviews
Pickering
10/10 – 16/10
$357/nighttotal: $2142 (6 )

Vacation Home In Pickering

3 4
apartment , Toronto
This modern apartment is located in Pickering, a peaceful suburb just 30 kilometres east of downtown Toronto, offering easy access to shopping, dining, and the Pickering Casino. It has excellent ratings for cleanliness, location, and user experience.
The spacious apartment covers 111 square metres and comfortably accommodates up to eight guests with three bedrooms and two bathrooms. It features a fully equipped kitchen, a private garden, a spa, and free parking for two cars, making it perfect for families or groups of friends.
Enjoy This Cozy 1 Bdrm Basement! - Pickering
10 11 reviews
Pickering
26/08 – 25/11
$99/nighttotal: $9009 (91 )

Enjoy This Cozy 1 Bdrm Basement!

1 2
apartment , Toronto
This family-friendly Ajax apartment, near downtown Ajax's amenities and shopping malls, offers easy access to Toronto, though precise distances to specific Toronto landmarks require knowing the exact address.
The freshly renovated one-bedroom property sleeps two (with a possible third person), features a queen-sized bed, a fully equipped kitchen, air conditioning, and excellent guest reviews; nearby parks and trails provide recreational opportunities.
City Comfort Meets Nature  Walk To Lake & Trails - Pickering
Pickering
01/08 – 31/08
$275/nighttotal: $8250 (30 )

City Comfort Meets Nature Walk To Lake & Trails

3 2
apartment , Toronto
This three-bedroom flat is located in the Scarborough district of Toronto, offering convenient access to local amenities and a reasonable distance from downtown attractions such as the Hockey Hall of Fame and the Royal Ontario Museum.
This furnished apartment accommodates up to six guests and includes a microwave, dishwasher, air conditioning, and free three-car parking, with the basement area excluded for privacy.

Frequently Asked Questions about vacation rentals in Pickering

  • What should a first-time visitor not miss in Pickering?

    For a first-time visit, you should definitely check out the Rouge National Urban Park. It's a beautiful spot with lots of walking trails and wildlife to see. If you're interested in history, head to the Pickering Museum Village to see what life was like in the 19th century.
  • What are the best Airbnb and vacation rentals in Pickering?

    Private Apartment W/separate Entrance, Mercedes Palace and Love And Relax At Dream Catcher Retreat are the most popular Airbnb and vacation rentals in Pickering among travelers.

  • Which neighborhood in Pickering should you consider for a vacation rental?

    The neighbourhood of Frenchman's Bay is a popular choice for vacation rentals. It's close to the waterfront and has a good selection of restaurants and shops. If you're looking for something more quiet, the neighbourhood of Rougemount is a good option.
  • What are the most popular Airbnbs in Pickering?

    Among the Airbnbs in Pickering, Private Apartment W/separate Entrance, Mercedes Palace and Love And Relax At Dream Catcher Retreat are the most popular ones.

  • What are the top family-friendly attractions in Pickering?

    Pickering has lots to offer families! The Toronto Zoo is just a short drive away and is a great day out for all ages. For a more local experience, head to the Pickering Museum Village for a glimpse into the past. The waterfront is also a great spot for families, with playgrounds and picnic areas.
  • What are the best vacation rentals with a pool in Pickering?

  • When is the best time to book a vacation rental in Pickering?

    The best time to book a vacation rental in Pickering is during the shoulder seasons, from April to June and September to October. You'll avoid the crowds and get better prices. If you're looking for a summer holiday, book well in advance as rentals tend to get booked up quickly.
  • What are the best rentals for families and kids in Pickering?

  • What events or festivals should visitors check out in and around Pickering?

    Pickering has a few events throughout the year, but the biggest one is the Pickering Village Festival in July. This is a great event for families, with live music, food stalls, and activities for kids. The nearby city of Toronto also has a lot of festivals and events throughout the year.
  • What are the best rentals or Airbnbs with a jacuzzi in Pickering?

  • What are the best budget-friendly activities in Pickering?

    There are plenty of free things to do in Pickering. Take a walk or cycle along the waterfront, visit the Pickering Museum Village, or explore the Rouge National Urban Park. You can also find free events at the Pickering Recreation Complex.
  • What are the best restaurants with local dishes in Pickering?

    For a taste of local cuisine, try the Pickering Village Restaurant. They have a great selection of traditional Canadian dishes. If you're looking for something a bit more casual, head to the Pickering Market for a variety of food stalls.
  • What are the best walking or cycling routes in Pickering?

    The Waterfront Trail is a great option for both walking and cycling. It stretches along the Lake Ontario shoreline and offers stunning views. For a shorter walk, try the Rouge National Urban Park trails.
  • Are there pet-friendly attractions in Pickering?

    The Rouge National Urban Park is a great place to bring your dog. There are plenty of trails and open spaces for them to run around. Many restaurants and cafes in the area also welcome dogs.
  • What are the benefits of choosing a vacation rental in Pickering?

    Vacation rentals offer more space and privacy than a hotel room. They can also be a more cost-effective option, especially for families or groups. Many rentals also offer amenities that you won't find in a hotel, such as a kitchen and laundry facilities.
  • What are the top sports attractions and facilities in Pickering?

    Pickering has a variety of sports facilities, including the Pickering Recreation Complex, which has a swimming pool, ice rink, and fitness centre. The city is also home to the Pickering Panthers, a junior hockey team that plays in the Ontario Junior Hockey League.

Destinations nearby

Best Pickering vacation rentals with a balcony

Family Home Near Toronto, Game Room, Backyard, Parking, Self-checkin - Pickering
9.3 18 reviews
Pickering
10/10 – 16/10
$404/nighttotal: $2424 (6 )

Family Home Near Toronto, Game Room, Backyard, Parking, Self-checkin

3 4
house , Toronto
This three-bedroom house is situated in Pickering, a suburb of Toronto, located 27 kilometres from the Ontario Science Centre and 37 kilometres from the Royal Ontario Museum, offering a peaceful escape from the city's hustle and bustle. The property has received excellent ratings for cleanliness, location and overall experience.
This spacious home, covering 19 square metres, comfortably accommodates up to seven guests. The house features a fully equipped kitchen, a private balcony with garden views, a water park, complimentary Wi-Fi, private parking, and is conveniently located near cycling and hiking trails.
Spacious 3 Bedroom Walkout Basement Apartment - Pickering
9.2 16 reviews
Pickering
10/10 – 16/10
$212/nighttotal: $1272 (6 )

Spacious 3 Bedroom Walkout Basement Apartment

3 4
apartment , Toronto
This three-bedroom Ajax apartment, situated approximately 5km from the Ajax Convention Centre and Deer Creek Golf Club, offers easy access to the Pickering Casino Resort.
Sleeping six guests, this self-catering property boasts two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, a Smart TV, on-site parking, and a terrace with garden access; it’s roughly a 30-40 minute drive from Toronto.
Home Away From Home! - Pickering
Pickering
14/08 – 29/08
$154/nighttotal: $2310 (15 )

Home Away From Home!

1 2
apartment , Toronto
This Pickering flat offers convenient access to Toronto attractions, situated approximately 12.5 kilometres from the Toronto Zoo and 37 kilometres from Yonge-Dundas Square.
This one-bedroom flat, measuring 37 square meters, accommodates up to three guests and features a private balcony, complimentary WiFi, private parking, and a kitchenette, with the Toronto Zoo a mere 12.5 kilometres away.
Luxury 2br Suite Stylish Stay With 2 Free Parking - Pickering
Pickering
14/08 – 29/08
$248/nighttotal: $3720 (15 )

Luxury 2br Suite Stylish Stay With 2 Free Parking

1 2
apartment , Toronto
This Pickering flat is situated 6.1 kilometres from the Toronto Zoo and over 27.4 kilometres from central Toronto's attractions, including the Ontario Science Centre and Distillery District.
This one-bedroom apartment accommodates up to nine guests and offers a fully equipped kitchen, air conditioning, complimentary WiFi, and a balcony and terrace, with free private parking available.

Best Pickering vacation rentals with air conditioning

Modern 3 Bedroom Home Surrounded By Parks - Pickering
9.2 10 reviews
Pickering
12/07 – 31/07
$353/nighttotal: $6707 (19 )

Modern 3 Bedroom Home Surrounded By Parks

1 6
apartment , Toronto
This Highland Creek, Toronto apartment is situated near the 401 highway, a 15-minute walk (approximately 1.2km) from the University of Toronto Scarborough campus, and within easy driving distance (around 10-20km depending on the attraction) of the Toronto Zoo and several parks including Morningside Park.
The three-bedroom property sleeps six guests, boasts a generously sized kitchen with quartz countertops and stainless steel appliances, a private backyard deck, four driveway parking spaces, ensuite laundry facilities, and high-speed Wi-Fi; ideal for families or groups visiting the city.
“Elysium” Where Happiness Is Real! - Pickering
9.9 416 reviews
Pickering
10/07 – 12/07
$196/nighttotal: $392 (2 )

“Elysium” Where Happiness Is Real!

1 2
apartment , Toronto
This basement flat is located in Pickering, a suburb east of Toronto, just a short drive from the Toronto Zoo, Pickering Casino, and Pickering Town Centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained flat can accommodate two guests and has a private entrance, ensuring privacy and independence. Guests can enjoy access to a range of amenities including a fully equipped kitchen, a comfortable living area with a TV and high-speed internet, and a private garden.
Roro's Comfy Basement - Pickering
10 3 reviews
Pickering
28/07 – 11/08
$182/nighttotal: $2548 (14 )

Roro's Comfy Basement

1 4
apartment , Toronto
This private basement flat offers its own entrance and two parking spaces in a well-connected Toronto district, convenient for accessing local amenities and attractions.
This dwelling accommodates four guests across two bedrooms with king-size beds, featuring a fully equipped kitchen, in-suite laundry, a dedicated workspace, and a 55-inch Smart TV.
Luxury4br | Steps To Lake Ontario| Near Go Station - Pickering
9.8 13 reviews
Pickering
10/10 – 16/10
$356/nighttotal: $2136 (6 )

Luxury4br | Steps To Lake Ontario| Near Go Station

1 5
apartment , Toronto
This Ajax apartment, near Lake Ontario and a short walk (approximately 1.6 km) from Ajax Waterfront Park and Duffins Creek, offers convenient access to local amenities including Sobeys supermarket, restaurants, and casinos.
The four-bedroom, three-bathroom property sleeps nine guests, features a modern kitchen with quartz countertops and stainless steel appliances, and includes parking, laundry facilities, and high-speed fibre internet; enjoy the open-plan living space with balcony and proximity to parks and trails including the Waterfront Trail.
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