
Vacation rentals with a pool in Pickering
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pickering
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Luxury Stay w/phenomenal view!
Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

2 BHK home 5 min from Go Train
7 min walk from Whitby train and Lake, this is a 2 BR house that offers accommodation with a 2 private parkings The self contained apartment is located in a brightly lit lower floor features, a separate entrance, a living room, and a fully equipped kitchen & laundry room. Guests can enjoy sun bathing in the garden or a barbque grill with your family. The backyard is shared however the guests have a private entrance. The pool is opens in june until September For monthly discounts contact us

Corner Unit in Liberty Village (Parking + Balcony)
Free parking available+ Close proximity to Budweiser Stage. Located in Liberty Village - one of Toronto’s most sought-after neighborhoods - this corner unit is a place to live, work, & play. The spacious, 700 sq ft layout offers 270-degree views of the city and Lake Ontario. With floor-to-ceiling windows, this 1 Bedroom + Den is flooded with natural light and zero wasted space. Enjoy a morning coffee or watch the sunset over cocktails on either of the two walk-out balconies.

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub
Unwind in style at our year-round heated pool & soothing hot tub—the heart of this luxury 4-bed family oasis. Inside you’ll find plush beds, smart TVs, speedy Wi-Fi and a fully stocked chef’s kitchen. Outside, enjoy the fenced backyard with BBQ, lounge seating and night lighting. Pool & hot tub open 365 days Baby gear: crib, high-chair, safety gates Games galore: board games, books & playroom Seconds to beaches, shops and dining—yet peaceful enough for stargazing.

Cozy 2 Bedrooms Suite - Good Location - Gym/Pool
Located in the center of Richmond Hill, this suite offers modern clean accommodations with a relaxing homey atmosphere. There is indoor pool, jacuzzi , Sauna and the air-conditioned gym. Everything you need can be found within walking distance, including many restaurants, a mall, even a large library. You can find many attractions a reasonable distance away, such as Canada's Wonderland, making this a perfect stopping point.

King West Triplex Main FLR PVT APT 1 BDRM Parking
KING WEST TRIPLEX Mainfloor unit is overlooking the Park and has a Pool in front, baseball and tennis courts, ping pong table and enclosed Dog Park! Hardwood floors, 12ft ceilings, private parking in the rear and a private back patio. Pets permitted. Two blocks from King and Bathurst, club, bars/patio restaurant district, and grocery store. Long term: Request 31 nights or more to avoid paying an additional 13% tax.

Pool/ King Bed/Wifi/Toronto LakeView/Free Parking
The Shopping & Dining Retreat Shop, dine, and relax in style. This chic 1-bedroom condo features high-end décor, a queen pull-out sofa, and a full kitchen. 🛍️ Just steps from a vibrant mall and countless restaurants. 🚆 Toronto is only 23 minutes away via GO. Perfect for weekend getaways, foodie trips, or retail therapy. Secure your dates now and enjoy the ultimate mix of comfort and city convenience!

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Modern 1 Bed Condo Mississauga
Stylish and central 1 Bed condo in Downtown Mississauga, steps to Square One, Celebration Square, Sheridan College, and transit. This modern unit features a bright open layout, full kitchen, fast Wi-Fi, smart TV, in-suite laundry, private balcony, and free parking. Walk to top restaurants, shops, events, and entertainment. Perfect for business travel, weekend getaways, shopping trips, and long stays.

Condo in Heart of Mississauga
Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

The Snug Oasis - Burrow (Near Airport)
Make some memories at this enchanting, family-friendly ranch style estate. Welcomed by old Oak trees and classic stone facades, your suite is on the ground floor. A warm wooden chamber abundant in antique charm, it overlooks the gorgeous garden and resort size pool. Birds chirping, bunnies visiting; nearby restaurants and poolside barbecues make it the perfect retreat!

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym
We are back! A Luxury 2-bedroom overlooking the city. Open concept living space with a modern flare and stainless steel appliances, encompassing the city life. Bedrooms have comfy queen beds and loads of closet space. Stunning views of the CN Tower and lake. Parking, Pool, Spa, Sauna, and gym access.
Popular amenities for Pickering rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Seraya Wellness Retreat

Home away from home with a hot tub and pool

Ravine Paradise ! heated pool and hot tub!

Countryside walk-out with pool.

The Ridge Roost - Uxbridge Township

Private Suite in New Custom Home with Private Pool

Chic King West Studio – TIFF & FIFA at Your Door
Condo rentals with a pool

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

Downtown Markham Unionville

Beautiful Condo Across CN Tower and MTCC

Lux Waterfront Condo Pool Hot Tub Free Parking

Luxury Condo with FreeParking. CN Tower Lake View

Stylish Downtown Toronto Condo with Free Parking

Stylish 1+1 Corner Suite |Steps to Lake&Downtown

Stylish 1BR/2 bed CN Tower view, Free Parking
Other vacation rentals with a pool

Rare 1BR - Rooftop Pool, Next to MTCC & CN Tower

Chic Richmond hill Condo

Entire Modern Condo Townhouse in Toronto

Presidential 2BR+Office in coveted Yorkville

CN Tower View 4BD Penthouse+Rogers Centre+Parking

Stunning Condo with View 2 Bedroom 2 Washroom

Lux Condo w/ Free Parking, King Bed, Clean, Quiet

Modern King Suite with Pool, Gym & City Views
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,862 GYD | G$42,903 GYD | G$42,487 GYD | G$43,736 GYD | G$32,490 GYD | G$30,407 GYD | G$32,490 GYD | G$37,696 GYD | G$34,364 GYD | G$30,824 GYD | G$29,574 GYD | G$27,908 GYD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about vacation rentals with a pool in Pickering

Total vacation rentals
Explore 50 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at G$4,165 GYD per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Pickering vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pickering rentals

4.8 Average rating
Pickering stays are highly rated by guests—averaging 4.8 out of 5!
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall
- Downsview Park
- Christie Pits Park




