
Condo vacation rentals in Pickering
Find and book unique condos on Airbnb
Quick stats about condo rentals in Pickering

Total vacation rentals
Explore 10 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at R 160 ZAR per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Wi-Fi availability
10 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!
Top-rated condo rentals in Pickering
Guests agree: these condos are highly rated for location, cleanliness, and more.

Spacious Luxury Condo w. Free Parking in Toronto!
Welcome To Tranquility in Toronto! A Sun-Filled Home with an Amazing View nestled beside a Toronto Golf Course! Walking distance to Walmart, grocery stores, Shoppers Drug Mart, LCBO/Beer Store and many restaurants. Highway and public transit within proximity to get you anywhere you need in the city! 55 inch TV in living room, along with 42 inch TV in the bedroom - both chromecast ready for all your favorite shows! Highspeed fibre optic internet also available for the duration of your stay!
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Toronto CN Tower 2 Bed 2 B w Master King w Parking
Luxury newly furnished home away from home in central downtown 300 Front Street with balcony CN Tower view. 2 Bedroom 2 Bath, Comfortable King bed TV en suit, Double bed TV w blackout curtains Enjoy in building Gym, Steam room, Outdoor pool with 360 degree view of the city, Whirlpool, and BBQ. Steps away from CN Tower, Rogers Centre, Aquarium, Metro Convention Centre, short walk to Scotiabank Arena, the lake, Bell Lightbox, Billy Bishop Airport, Union Station, Entertainment District and more
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3BR Penthouse with Panoramic Views + Large Terrace
Experience Luxury downtown living in the sky from this stunning 3-bedroom Penthouse Suite featuring breathtaking lake, skyline & Rogers Centre views from a private 400 sq.ft. terrace. Enjoy 1,400 sq.ft. of beautifully designed living space, 2.5 baths, a spa-inspired primary suite & free 2 car parking. Premium amenities include rooftop pool, hot tub, cabanas, BBQ area & gym. Steps to the CN Tower, Convention Centre, waterfront, Union STN & Toronto’s top attractions. Perfect for families & groups.
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Luxury Downtown Condo For 4 (CN Tower Views)
Step into luxury at this stylish condo that sleeps 4 nestled in the vibrant Entertainment District. Immerse yourself in city life with proximity to iconic attractions such as the CN Tower, Metro Convention Centre, Rogers Centre, & Scotia Bank Arena—all just steps away. A short stroll leads you to an array of upscale dining, shopping, and entertainment options. Enjoy the modern and tranquil ambiance we've curated within the unit, while taking in the breathtaking CN Tower view from the balcony.
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Luxury Downtown Condo For 6 (CN Tower View)
Luxury awaits in our sophisticated 2bed, 2bath condo in the Entertainment District. This prime location places you steps away from Toronto's CN Tower, Metro Convention Centre, Rogers Centre, Hockey Hall of Fame & Scotia Bank Arena. Within a short walk, explore plenty of top dining, shopping, and entertainment options. Our unit is meticulously designed for modernity, elegance, and a truly relaxing experience. Enjoy our updated balcony with seating arrangements & breathtaking CN Tower views.
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The Penty: Luxurious Penthouse with Pool, Hot Tub
Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core
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Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.
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Luxury Lakeview 3BR+2BA Condo • Subway & BMO Field
Welcome to this luxury 3-bedroom, 2-bath lakeview condo in downtown Toronto. Enjoy stunning views of Lake Ontario and the CN Tower in a modern, comfortable space perfect for families, business travelers, or groups. Only a 3-minute walk to TTC Osgoode Subway Station, and about 15 minutes by subway to BMO Field, one of the 2026 FIFA World Cup venues. Close to Toronto’s best restaurants, shopping, nightlife, entertainment, and major attractions. *Not ideal for parties *Must be quiet
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Debonair Condo Heart of Toronto w/Free Parking
Enjoy a stylish experience at our centrally located home. Take advantage of charming cafes, Michelin-star restaurants, and boutiques at your doorstep. Steps from the following (walking times) - Financial District - 9 min - St. Lawrence Market - 6 min - Eaton Centre - 12 min - Distillery District - 18 min - St. Michael's Hospital - 9 min Note: there is a new condo building under construction which partially obstructs the view. This is not yet captured in the photo.
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70% Off Monthly Stuning Balcony View STEP To CN
This is a fully furnished 2 BED + 2FULL BATH. CORNER UNIT Free Parking included/Full kichen WITH Greatest Balcony with View of the CN Tower and Rogers Centre. Scotia arena .Aquarium Ripleys, Lake,Union Station ,MTCC Only 2 min walk to All above+15 min Walk to museium + City Hall+ Eaton Center Mall +path to longoes+star+Lcbo Starbox+scotia arina+tens of other places and fine resturants. Highlights: → Secured building access with 24/7 concierge
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Central condo in heart of Liberty Village +parking
Right on the park! Stay in one of Toronto’s most vibrant neighborhoods. This modern space includes high-speed Wi-Fi, dedicated workspace, large HDTV, in-unit laundry, and access to a private gym. ALL amenities withing walking distance Steps to cafés, nightlife, transit, parks, and more. Walk to the Waterfront, BMO Field, RBC Amphitheatre, Enercare center, CNE, Fort York, and top attractions—perfect for work or play.
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Gorgeous & Modern 2Bed 2Bath Sq1 Condo Corner unit
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 well equippedand gym and games room. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto
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Popular amenities for Pickering condo rentals
Weekly condo rentals

Cozy Studio w/Private entrance & Bathroom
ValueCleanlinessHospitality

Modern Downtown Unionville Stay
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Luxury Penthouse | Skyline Views | Markham
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5-Star 2BR/2BA with Pool & Gym | Yonge & Eglinton
ValueFamilyTV

Stylish Urban Condominium STR-2308-JDYBHz
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Charming Bowmanville Getaway | Quiet & Comfy
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Furnished 1+Den|two bathrooms Richmondhill-Parking
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Modern 1BR Markham Condo | Pool, Gym & Parking
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Pet-friendly condo rentals

Modern 1BR Toronto Downtown Condo, King size bed
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Steps to CN Tower/Waterfront | 2BR/2BA + Parking
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Bright & Cozy Condo w/ Private Balcony - Ent. Dist
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The Beaches pied-á-terre (Woodbine Beach)
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Charming Condo w Parking, CN Tower View & Pool
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Humber Bay Family Friendly condo w Terrace&Parking
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College Park :2Bd+2bth + Free parking
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Heart of TO, Entertainment & Financial districts
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Condo rentals with a pool

Luxury Downtown Condo For 6 (Near CN Tower)
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1BR+Den|Parking&Pool|UnionStation|CNTower&Arena
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Yorkville Luxury Suite | Pool, Sauna & Gym Toronto
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Central downtown condo next2 CNtower+free parking
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Modern 2BR 2BATH Urban Core Hotel-Style Condo
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Lakeside Condo /Pool/ Walking Trail/Parking/CNE
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Luxury CN Tower View, 2BR, Free Parking
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Modern 1+Den condo steps away from CN Tower & Lake
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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Coca Cola Coliseum
- Enercare Centre
- Massey Hall
- Vaughan Mills





