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Best Vacation rentals and Airbnb offers in Pickering
9.5 46 reviews
Pickering
10/20 – 04/27
$46/nighttotal: $8694 (189 )
1 Bedroom Studio Private Basement In Pickering
1 2
apartment , Toronto
This Toronto basement studio is centrally located in a family-friendly neighborhood, offering easy access to Toronto's attractions, though specific distances aren't provided. The unit sleeps two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, a bathroom with toiletries, air conditioning, and street parking.
9.6 92 reviews
Pickering
10/10 – 10/16
$207/nighttotal: $1242 (6 )
Entire Home In Ajax With Children's Play Area
1 4
apartment , Toronto
This Ajax, Ontario house rental is conveniently located near Highway 401, providing easy access to Toronto and Lake Ontario (under 10 minutes away). The 4-bedroom, 2-bathroom home sleeps eight guests and features a fully equipped kitchen, free high-speed internet, Netflix, on-site parking for three vehicles, and a children's play area.
Pickering
06/27 – 07/04
$110/nighttotal: $770 (7 )
Bright & Modern Private Basement Suite
2 2
apartment , Toronto
This newly renovated 2-bedroom, 1-bathroom apartment in a quiet Toronto residential area offers a private entrance and a fully equipped kitchen, providing a peaceful stay with convenient access to the city's attractions. With a guest capacity of 4, this suite features high-speed Wi-Fi, air conditioning, and a spacious glass shower, making it ideal for families or business travelers seeking comfort and modern amenities.
9.5 44 reviews
Pickering
07/28 – 08/11
$137/nighttotal: $1918 (14 )
2 Bedroom Legal Basement Apartment
1 4
apartment , Toronto
This basement apartment is located in a residential area of Toronto, within a 30-minute drive of the CN Tower and Rogers Centre. Guests consistently rate the apartment excellent for its cleanliness, location, and overall experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to five guests. It features a private entrance, a full kitchen with stainless steel appliances, and amenities like air conditioning, parking, and internet access.
Pickering
10/10 – 10/16
$175/nighttotal: $1050 (6 )
Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront
4 4
house , Toronto
This 4-bedroom house in Ajax offers proximity to the waterfront, is 1.5 miles from Paradise Beach, and is within driving distance of Toronto landmarks, including the Toronto Zoo (12 miles) and Ryerson University (25 miles). This 1800 sq ft accommodation accommodates up to 15 guests and features a fully equipped kitchen with a dishwasher and microwave, complimentary WiFi, air conditioning, and 2-car parking.
8.0 4 reviews
Pickering
10/10 – 10/16
$120/nighttotal: $720 (6 )
Brand New 2 Bedroom Basement Apartment
2 4
apartment , Toronto
This fully furnished two-bedroom, two-bathroom basement apartment rental in Ajax, Ontario, offers easy access to major highways and attractions such as Parkwood Estate and the Markham Museum, minimizing travel time to Toronto. The 2-bedroom unit sleeps four guests and includes a fully equipped kitchen with a refrigerator and microwave, air conditioning, a garden, a spa, parking, and high-speed internet; nearby entertainment options include Cineplex Cinemas Pickering and Deer Creek Golf Course.
9.8 57 reviews
Pickering
10/10 – 10/16
$167/nighttotal: $1002 (6 )
Entire Home North Scarborough
1 5
apartment , Toronto
This three-bedroom Toronto home, located in a quiet neighborhood between Markham and Scarborough, provides easy access to Highway 401 and is under 40 minutes from downtown Toronto and Pearson International Airport. This family-friendly house boasts a fully equipped kitchen with a fridge, microwave, and dishwasher, a private patio, smart lock entry, and accommodates up to six guests with two bathrooms; board games are available for entertainment.
Pickering
06/27 – 07/24
$144/nighttotal: $3888 (27 )
Spacious 1 Bedroom Apartment To Yourself. Perfect For Solo Traveller Or Couples
1 1
apartment , Toronto
This Ajax condo is a 16-minute drive to the Toronto Zoo and 19 minutes to Scarborough Town Centre, offering convenient access to Toronto attractions. This 1-bedroom, 1-bathroom unit sleeps 2 guests and features air conditioning, Wi-Fi, a full kitchen with microwave, and on-site parking, with a barbecue available for outdoor cooking.
Pickering
07/28 – 08/11
$244/nighttotal: $3416 (14 )
Modern 3bedroom Apartment In Prime Pickering Location
3 4
apartment , Toronto
This Toronto area condo in Pickering, Ontario, is located a 3-minute drive from Pickering GO Station, providing convenient access to downtown Toronto in approximately 30 minutes, and is also a 3-minute drive from Pickering Town Centre. This 3-bedroom, 2-bathroom condo accommodates up to 6 guests and offers amenities such as high-speed Wi-Fi, free parking for one vehicle, in-unit laundry, a work desk, Smart TVs with Netflix, and a private primary suite with an en-suite bathroom.
10 3 reviews
Pickering
06/23 – 07/23
$172/nighttotal: $5160 (30 )
Toronto/lakeside Home
1 4
apartment , Toronto
This Toronto apartment rental in West Rouge, Scarborough, offers unparalleled access to Rouge Beach Park (a 2-minute walk) and Rouge Hill GO Transit station (5-7 minutes away), providing easy exploration of Rouge National Urban Park. The two-bedroom, one-bathroom unit sleeps four, boasting a private side yard with a hot tub, BBQ, and fireplace, plus lake views from upper rooms, a fully equipped kitchen, and in-unit internet access.
10 132 reviews
Pickering
08/14 – 08/29
$138/nighttotal: $2070 (15 )
Ultra-modern Luxury Retreat! Close To Thermea Spa.
1 2
apartment , Toronto
This one-bedroom rental is located in the quiet, family-friendly neighborhood of Ajax, just 10 minutes from the Thermea Spa. The apartment has excellent user, location, and cleanliness ratings. The apartment has a modern open-concept layout and can accommodate two guests. Amenities include a patio area, a wine fridge, a SONOS music system, an Atmos air purifier, a Level 2 EV charger, and laundry for stays of five days or longer.
10 3 reviews
Pickering
07/15 – 07/15
$256/nighttotal: $93440 (365 )
Cute Corner Model Home By Brock&taunton In Whitby.
4 3
apartment , Oshawa
This four-bedroom, three-bathroom apartment in Oshawa offers an excellent user and location rating, and very good cleanliness rating. It is pet-friendly and has a kitchen, air conditioning, parking, and internet. With a guest capacity of eight, this apartment is perfect for families or groups of friends. It is located in a quiet neighborhood, just a short walk from the city center. The apartment has a fully equipped kitchen, a comfortable living room, and a private balcony.
Top Vacation Rentals for Families in Pickering
These family-friendly vacation rentals in Pickering offer spacious layouts and easy access to top city attractions.
8.8 20 reviews
Pickering
10/10 – 10/16
$284/nighttotal: $1704 (6 )
Furnished Family Home King Bed Parking Bbq Backyard Discounted Price
3 5
apartment , Toronto
This Pickering vacation home, near Lake Ontario and Rouge National Urban Park, offers easy access to Toronto-area attractions within a 5-10 mile radius. This 2,500-square-foot property boasts three bedrooms, two bathrooms, sleeps six, and includes a private fenced yard, swimming pool, spa, tennis court, and barbecue grills; enjoy free Wi-Fi and on-site water park fun.
9.7 127 reviews
Pickering
09/04 – 09/07
$139/nighttotal: $417 (3 )
Brand New 2 Bedroom Basement Apartment (1)
1 3
apartment , Toronto
This basement apartment is conveniently located in a central Toronto neighborhood, close to major stores and highways, making it easy to explore the city. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience. This two-bedroom, one-bathroom rental comfortably accommodates up to four guests. The apartment is fully furnished, including a kitchen with a fridge, freezer, and microwave, plus air conditioning and free parking, making it a convenient and comfortable choice for travelers.
10 6 reviews
Pickering
07/30 – 08/05
$502/nighttotal: $3012 (6 )
Modern Nest - 4 Br House, 5 Beds, 2.5 Baths, 3 Park
4 2
apartment , Oshawa
This Pickering vacation home, a 12-minute drive from the Toronto Zoo and 19-minute drive from Scarborough Town Centre, offers convenient access to major attractions. This four-bedroom, three-bathroom house sleeps ten guests and includes a fully equipped kitchen, laundry facilities, a tennis court, and covered parking; nearby amenities include the Cedarena Ice Rink and Cineplex Pickering Cinemas.
Pickering
06/25 – 10/16
$250/nighttotal: $28250 (113 )
7 Bedroom And 6 Washroom House With 2 Kitchen And 2 Laundry And A Huge Backyard
3 2
apartment , Toronto
This Scarborough, Toronto vacation home is situated near Lake Ontario (2.3 miles), Scarborough Town Centre (3 miles), and Bluffer's Park, with easy access to Eglinton Station. This 1,800-square-foot house sleeps eight, features three bedrooms, a fully equipped kitchen, free Wi-Fi, air conditioning, a private yard with a playground, and parking.
Best Pickering vacation rentals with parking
Pickering
06/23 – 07/23
$711/nighttotal: $21330 (30 )
Upscale Pickering Escape | Near Lake & Dining
5 4
apartment , Toronto
This five-bedroom, five-bathroom Pickering rental is an 11-minute walk from Lake Ontario and a 10-minute drive from Toronto attractions like the Toronto Zoo and Cineplex Pickering. The 10-guest home features a fully equipped kitchen, in-unit laundry, parking, air conditioning, Wi-Fi, and a fireplace, offering convenient self-catering and comfortable entertainment options.
Pickering
10/10 – 10/16
$205/nighttotal: $1230 (6 )
Modern 4‑bedroom Retreat I 2‑car Parking I Steps From The Ajax Waterfront
4 4
house , Toronto
This modern 4-bedroom house is located in Ajax, Ontario, just a 1-minute drive from Lake Ontario and Ajax Waterfront Park, with Costco and Walmart a short drive away. This family-friendly rental offers 1790 square feet of living space with 4 bedrooms and 5 bathrooms, accommodating up to 8 guests with features like a main-floor bedroom, an open-concept living area, and parking for 2 vehicles.
Pickering
06/27 – 07/04
$409/nighttotal: $2863 (7 )
King Bed Convenience On Main Floor
4 2
apartment , Toronto
This 3-bedroom house is located in Ajax, Canada, offering convenient access to major routes and highways, with nearby attractions like Durham Regional Forest and Ajax Waterfront Park. This pet-friendly rental features 2690 square feet of living space, a fully equipped kitchen with a dishwasher, and an outdoor patio, accommodating up to 6 guests.
Pickering
08/26 – 11/25
$99/nighttotal: $9009 (91 )
Luxury Lakeview Condo • Steps To Sandy Beach
1 2
apartment , Toronto
This Toronto condo offers proximity to Sandy Beach and is a 5-minute walk to the GO Station, providing convenient access to downtown Toronto and Pickering Town Centre. This apartment features a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, fitness center, parking, one bathroom, and accommodates two guests, ideal for a peaceful escape.
Frequently Asked Questions about vacation rentals 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, like spring and fall. The weather is still pleasant, and the crowds are smaller. You'll also find better deals on rentals during these times.
What are the best Airbnb and vacation rentals in Pickering?
What are the best budget-friendly activities in Pickering?
Pickering offers a lot of free activities, like exploring the Rouge National Urban Park or taking a walk along the waterfront. You can also check out the Pickering Museum Village, which offers free admission on Tuesdays.
What are the best restaurants with local dishes in Pickering?
For a taste of local cuisine, try the Pickering Village Restaurant. They offer a variety of dishes, including Canadian comfort food. Another option is the Pickering Fish Market, which serves fresh seafood.
What are the best vacation rentals with a pool in Pickering?
What are the best walking or cycling routes in Pickering?
The Waterfront Trail is a popular walking and cycling route that runs along the shores of Lake Ontario. It offers scenic views of the lake and the city. You can also check out the Rouge National Urban Park, which has a variety of hiking trails.
What are the best rentals for families and kids in Pickering?
Yes, the Rouge National Urban Park is pet-friendly. You can bring your furry friend for a walk on the trails or a swim in the lake. Many restaurants also have outdoor patios that are pet-friendly.
What are the best rentals or Airbnbs with a jacuzzi in Pickering?
What are the benefits of choosing a vacation rental in Pickering?
Vacation rentals offer more space and privacy than a hotel room. They are often located in residential areas, which gives you a more authentic experience of the city. They can also be more affordable than hotels, especially for families or groups.
What are the top sports attractions and facilities in Pickering?
The Pickering Recreation Complex is a popular spot for sports and recreation. It has an indoor pool, fitness center, and ice rink. The city also has several parks and fields for outdoor sports.
Destinations nearby
Best Vacation Rentals with Balconies in Pickering
Wake up to breathtaking views at these Pickering vacation rentals with balconies, perfect for your morning coffee.
Pickering
08/21 – 09/07
$289/nighttotal: $4913 (17 )
Modern Gem| 2026 Fifa - 40 Mins To Bmo Field | Thh
3 2
house , Toronto
This three-story townhouse, located in Ajax, Ontario, offers easy access to Toronto attractions like the Toronto Zoo and Markham Museum, and is a short drive from Lynde Shores Conservation Area. This 2167-square-foot (1990 sq ft converted from metric) rental boasts three bedrooms, three bathrooms, and can comfortably accommodate up to ten guests, featuring a fully equipped kitchen, Wi-Fi (3.5 Gbps), a patio, parking, and in-unit laundry.
9.8 7 reviews
Pickering
07/28 – 08/11
$309/nighttotal: $4326 (14 )
3-bed 3-bath Cozy Vacation House In Ajax, Greater Toronto Area Gta, On, Canada
3 4
apartment , Toronto
This Ajax, Ontario vacation home is conveniently located 1.5 miles from the Ajax Convention Centre and 2.1 miles from the Pickering Casino Resort, offering easy access to Toronto attractions. This 1990-square-foot property boasts three bedrooms, three bathrooms, accommodates six guests, and features a swimming pool, jacuzzi, and on-site water park for ultimate relaxation and entertainment.
9.6 14 reviews
Pickering
08/23 – 08/26
$799/nighttotal: $2397 (3 )
Stunning 7 Br Rougeview Home With 2 Kitchens, 5 Bathrooms, Amazing Backyard & 8-car Parking
7 1
house , Toronto
This 7-bedroom home is located in Toronto, just a short drive from the Toronto Zoo and within easy reach of other popular attractions like the Ontario Science Centre and the Royal Ontario Museum. The house has consistently received excellent ratings for its cleanliness, location, and overall experience. This spacious home, spanning 3,000 square feet, comfortably accommodates up to 20 guests. The home includes modern amenities like air conditioning, free Wi-Fi, flat-screen TV, and private parking, as well as a backyard with an outdoor dining area, garden, and play equipment.
9.3 205 reviews
Pickering
07/03 – 07/07
$535/nighttotal: $2140 (4 )
Beautiful Lakeview Cottage On The Beach
3 10
cottage , Ajax
This charming cottage is located just 20 minutes east of Toronto, right on Paradise Beach in south Ajax, Ontario. The cottage has received excellent ratings for its cleanliness, location, and overall experience. The cottage has 3 bedrooms and 2 bathrooms, with a total of 2,200 square feet of living space, comfortably accommodating up to 11 guests. Enjoy a fully equipped kitchen, laundry facilities, a terrace, a garden, and a BBQ grill, as well as direct access to the beach and all its activities.
Best Pickering vacation rentals with air conditioning
9.9 91 reviews
Pickering
07/30 – 08/05
$160/nighttotal: $960 (6 )
Miden Touch: Stylish Modern Basement W/ Workspace
1 2
apartment , Toronto
This modern basement suite is conveniently located in Ajax, just a 10-minute drive from the Ajax Waterfront and close to Highway 401, making it easy to explore Toronto and its surrounding areas. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The suite offers a private entrance and comfortably accommodates up to four guests. The fully equipped kitchen, dedicated workspace, and laundry facilities provide everything you need for a comfortable and convenient stay.
9.8 10 reviews
Pickering
08/01 – 08/31
$88/nighttotal: $2640 (30 )
Private| Close To Lake | 30 Min. To Downtown| Wifi
1 2
apartment , Toronto
This basement apartment is located in a suburban area of Toronto, about 30 minutes from downtown and a short drive from the Toronto Pan Am Sports Centre. The apartment has earned excellent ratings for its cleanliness, location, and user experience. The apartment is a self-contained unit with one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a fully equipped kitchen, a 55-inch smart TV, high-speed Wi-Fi, laundry facilities, and private parking.
9.9 416 reviews
Pickering
06/30 – 07/31
$114/nighttotal: $3534 (31 )
“Elysium” Where Happiness Is Real!
1 2
apartment , Toronto
This basement suite is located in Pickering, a suburb east of Toronto, just a short drive from the Toronto Zoo, Pickering Casino, and Pickering Town Centre. The apartment has received excellent ratings for user experience, location, and cleanliness. This private, walk-out basement suite can comfortably accommodate two guests and features a separate street and building access for privacy. Guests can enjoy amenities such as free parking, Bell Fibe wifi, a TV with 1000+ streaming channels, an iPad to control the temperature, and laundry access for stays of 5 nights or longer.
Pickering
07/15 – 07/15
$155/nighttotal: $56575 (365 )
Unit 10 - Modern Fully Furnished 2 Bedroom Apartment
2 3
apartment , Toronto
This 2-bedroom, 2-bathroom condo in Scarborough, Toronto, is located within walking distance of convenience stores and restaurants, and is approximately 5 miles from Markham Village and Markham Museum, and 3 miles from the Toronto Zoo. This fully furnished apartment offers a complete kitchen, a living room with a sofa and television, complimentary WiFi, and accommodates up to 4 guests, with air conditioning and pets allowed.