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Pickering short term rentals
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Best Short term and Weekly rentals in Pickering

Compare 5-Star Lodgings in Pickering

Experience the pulse of the city from a luxury rental in central Pickering, where every urban convenience is at your fingertips.

Sunny & Clean 2-level Private Suite In Ajax - Pickering
9.2 25 reviews
Pickering
08/14 – 08/29
$76/nighttotal: $1140 (15 )

Sunny & Clean 2-level Private Suite In Ajax

1 2
apartment , Toronto
This Toronto rental is conveniently located near major highways and a short walk from Costco, McDonalds, Canadian Tire, Best Buy, a gas station, banks, and public transportation. Guests have consistently rated this apartment as excellent for its cleanliness, location, and overall experience.
This one-bedroom, one-bathroom dwelling comfortably accommodates up to four guests. The apartment includes air conditioning, internet access, and a kitchen equipped with a fridge, making it easy to relax and enjoy your stay in Toronto.

Best Pickering Short term rentals with a jacuzzi

Among the 936 accommodations in Pickering, here are the 4 best rentals with a jacuzzi

Assets Event Venue Modern Interior With Elegant Décor. - Pickering
9.2 16 reviews
Pickering
10/10 – 10/16
$1686/nighttotal: $10116 (6 )

Assets Event Venue Modern Interior With Elegant Décor.

6 4
apartment , Oshawa
This spacious home is located in north Whitby, about 45 minutes north of downtown Toronto, offering a quiet escape from the city while still being close to attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests. This multi-level home can accommodate up to 20 guests and features a large loft space, perfect for gatherings. The property offers a wide range of amenities, including a pool, hot tub, gym, and a variety of event hosting capabilities, making it ideal for both families and large groups.
Ravine Paradise ! Heated Pool And Hot Tub! - Pickering
9.8 108 reviews
Pickering
10/10 – 10/16
$422/nighttotal: $2532 (6 )

Ravine Paradise ! Heated Pool And Hot Tub!

1 4
apartment , Toronto
This newly renovated bungalow is located in the Rouge River Valley, close to the Rouge International Urban Park and easy access to trails, beaches, and waterfront. The home has excellent user, location, and cleanliness ratings.
This 3-bedroom, 2-bathroom home can accommodate up to 6 guests. The home includes a private backyard with a pool, outdoor fireplace, and seating for 16, plus a fitness center, parking for 6 vehicles, and a swimming pool.
Upscale Pickering Escape | Near Lake & Dining - Pickering
Pickering
06/27 – 07/24
$806/nighttotal: $21762 (27 )

Upscale Pickering Escape | Near Lake & Dining

5 1
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.
Toronto/lakeside Home - Pickering
10 3 reviews
Pickering
06/25 – 10/16
$164/nighttotal: $18532 (113 )

Toronto/lakeside Home

1 2
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.

Frequently Asked Questions about short term rentals in Pickering

  • Which top landmarks you shouldn't miss in Pickering?

    You should definitely check out the Pickering Museum Village, a living history museum showcasing life in 19th-century Ontario. The Rouge National Urban Park is a must-see for nature lovers, with hiking trails, scenic views, and diverse wildlife. And for a unique experience, visit the Toronto Zoo, just a short drive from Pickering.
  • What are the best short term rentals in Pickering?

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

  • What kind of weather can travelers expect in Pickering?

    Pickering has a humid continental climate, so you can expect warm, humid summers with average highs in the 80s Fahrenheit and cold, snowy winters with average lows in the 20s. Spring and fall offer pleasant temperatures, making them ideal for outdoor activities.
  • What are the best short term rentals with a pool in Pickering?

  • What are the most popular festivals and events in Pickering?

    The Pickering Village Festival is a popular summer event with live music, food, and craft vendors. The Pickering Pumpkinfest in October features pumpkin carving, a parade, and other family-friendly activities. The annual Canada Day celebrations at the Pickering Recreation Complex are always a big hit with fireworks and live entertainment.
  • What are the best short term rentals with a jacuzzi in Pickering?

  • Are there any famous stadiums or sports arenas in Pickering?

    There are no major stadiums or sports arenas in Pickering itself. However, the Rogers Centre in downtown Toronto, home to the Toronto Blue Jays baseball team, is easily accessible from Pickering by car or public transportation.
  • What are the best short term rentals for families and kids in Pickering?

  • What notable natural landmarks are near Pickering?

    The Rouge National Urban Park, located just south of Pickering, is a great spot for hiking, birdwatching, and enjoying nature. The shores of Lake Ontario are also nearby, offering scenic views and opportunities for swimming, fishing, and boating.
  • What part of Pickering is ideal for finding lodging?

    The area around the Pickering Town Centre, with its shopping, dining, and entertainment options, is a good choice for lodging. The neighborhoods of Dunbarton and Rouge Park are also popular with visitors, offering a quieter atmosphere and easy access to the Rouge National Urban Park.

Destinations nearby

Browse Family Short-Term Rentals in Pickering

Choosing a family-friendly rental in Pickering ensures the city’s top attractions are within easy reach.

Sleep 8 | Toronto Hub| Thermëa Spa | Iroquois Park - Pickering
10 2 reviews
Pickering
08/26 – 11/25
$148/nighttotal: $13468 (91 )

Sleep 8 | Toronto Hub| Thermëa Spa | Iroquois Park

1 2
apartment , Oshawa
This spacious 3-story townhouse is located in downtown Whitby, a short drive from Thermëa Spa Village and less than 2 miles from Iroquois Park Sports Centre, offering convenient access to dining and shopping. This family-friendly apartment accommodates up to 8 guests with 3 bathrooms, a chef's kitchen featuring a quartz waterfall island and stainless steel appliances, a private backyard, and a finished basement, ideal for spa days and sports tournaments.
Detached 3 Br Home In Ajax,on - Pickering
9.5 122 reviews
Pickering
10/10 – 10/16
$231/nighttotal: $1386 (6 )

Detached 3 Br Home In Ajax,on

4 5
apartment , Toronto
This 4-bedroom home is located in a quiet suburban area, just a short drive from attractions like the Toronto Zoo and Ontario Science Centre. The property has consistently received excellent ratings for user experience, location, and cleanliness.
This spacious rental offers 1,700 square feet of living space, comfortably accommodating up to 8 guests. Enjoy a fully equipped kitchen, a private garden, free parking, and amenities like air conditioning, a Jacuzzi, a washer and dryer, and free Wi-Fi.
Guest Basement In Scarborough - Pickering
Pickering
10/20 – 04/27
$73/nighttotal: $13797 (189 )

Guest Basement In Scarborough

2 2
apartment , Toronto
This Toronto basement apartment rental is located in Scarborough's Rouge Park neighborhood, a 10-minute drive from the University of Toronto Scarborough campus and the Pan Am Sports Centre.
This two-bedroom, one-bathroom unit sleeps six, features a fully equipped kitchen with island, in-unit laundry, air conditioning, parking, and is near Rouge National Urban Park and the Upper Rouge Trail.
A Luxurious Custom Built Home Designed With Passion, Located Port Union Village - Pickering
10 1 review
Pickering
10/01 – 10/31
$170/nighttotal: $5100 (30 )

A Luxurious Custom Built Home Designed With Passion, Located Port Union Village

4 2
apartment , Toronto
This 4-bedroom, 3-bathroom condo in Scarborough, Toronto, offers a family-friendly stay, located less than 1 mile from the Toronto Zoo and Cedarena, and within convenient reach of Birchmount Park and Markham Pan Am Centre.
This spacious unit features ample natural light, an open-concept living area with marble and hardwood floors, a chef's kitchen with quartz countertops, and a master suite with a private balcony, plus a child-friendly backyard with a deck and playground.

Best Pickering lodging with parking

3-bed 3-bath Cozy Vacation House In Ajax, Greater Toronto Area Gta, On, Canada - Pickering
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.
Guest Suite In Ajax/toronto - Pickering
Pickering
08/14 – 08/29
$91/nighttotal: $1365 (15 )

Guest Suite In Ajax/toronto

1 2
apartment , Toronto
This newly renovated 1-bedroom condo in Ajax offers convenient access to natural attractions, including Rouge National Urban Park, Darlington Provincial Park, and the Toronto Zoo, all within a short drive.
This modern dwelling accommodates up to two guests and features a custom kitchen, dedicated office space, and a stylish bathroom, with air conditioning and internet provided for a comfortable stay.
Enjoy This Cozy 1 Bdrm Basement! - Pickering
10 11 reviews
Pickering
06/27 – 07/24
$97/nighttotal: $2619 (27 )

Enjoy This Cozy 1 Bdrm Basement!

1 1
apartment , Toronto
This family-friendly Ajax rental, near downtown Ajax's amenities, shopping malls, theaters, restaurants, parks, and trails, offers easy access to Toronto attractions, though exact driving distances aren't specified.
The one-bedroom, one-bathroom apartment sleeps up to three guests and features a queen-sized bed, a full kitchen, air conditioning, and excellent guest ratings for cleanliness and location; it is freshly renovated.
Comfortable Private Space - Pickering
9.7 992 reviews
Pickering
10/10 – 10/16
$151/nighttotal: $906 (6 )

Comfortable Private Space

2 4
B&B , Toronto
This charming bed and breakfast is conveniently located in a suburban area of Toronto, just a short drive from attractions like the Toronto Zoo, Ontario Science Centre, and Royal Ontario Museum. Guests consistently rave about the excellent location, cleanliness, and overall experience.
Each unit features a private bathroom with a walk-in shower, ensuring privacy and comfort. Modern amenities like air conditioning, flat-screen TV, oven, microwave, coffee machine, free parking, and Wi-Fi make for a comfortable and convenient stay.
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