
Holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pickering rentals with a pool
House rentals with a pool

Beautiful Cottage in Ajax

Home away from home with a hot tub and pool

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Luxury Spa Escape w/ Pool & Jacuzzi + Private Chef

Ravine Paradise ! heated pool and hot tub!

Guest suite 10 min to subwy w kitchen FREE parking

Luxe, Family-Friendly Oasis Home With Outdoor Pool

private backyard SPA oasis in Toronto
Apartment rentals with a pool

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

Beautiful Condo Across CN Tower and MTCC

Chic, High-Rise Apartment with CN Tower Views

Luxury 1BR Executive Condo • Panoramic City Views

Luxury 1 Bedroom Suite In Heart Of Toronto

Luxury Downtown Condo For 6 (Near CN Tower)

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

FREE Parking! CN Tower Views! Rooftop Pool!
Other holiday rentals with a pool

Luxury House with a Bright Sunroom & a heated pool

Charming Condo with Private Terrace in Etobicoke!

1 BDRM Luxury Loft By Square One w/FREE PARKING

1 Bed BRAND NEW Condo-Stunning T.O. Views

Bright, spacious luxury basement apartment

Modern 1 Bed Condo Mississauga

Stylish Apt. Pool, BBQ + Malls. 25 Mins to Toronto

Award Winning 3BR Luxury Penthouse •Stunning Views
Quick stats about holiday rentals with a pool in Pickering
Total rentals
50 properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
690 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Capital District, New York Holiday rentals
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
- Island of Montreal Holiday rentals
- Rentals with a washing machine and dryer Pickering
- Apartment rentals Pickering
- Rentals with lake access Pickering
- Rentals with beach access Pickering
- Family-friendly rentals Pickering
- Fitness-friendly rentals Pickering
- House rentals Pickering
- Private suite rentals Pickering
- Rentals with outdoor seating Pickering
- Rentals with an EV charger Pickering
- Cottage rentals Pickering
- Smoking-friendly rentals Pickering
- Rentals with a fireplace Pickering
- Rentals with a patio Pickering
- Beachfront rentals Pickering
- Pet-friendly rentals Pickering
- Guest house rentals Pickering
- Rentals with breakfast Pickering
- Rentals with a firepit Pickering
- Waterfront rentals Pickering
- Rentals with a hot tub Pickering
- Townhouse rentals Pickering
- Flat rentals Pickering
- Rentals with pools Durham Region
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Financial District
- Exhibition Place
- Toronto Zoo
- Harbourfront Centre
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Jackson-Triggs Niagara Estate
- Toronto City Hall
- Royal Woodbine Golf Club