
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 163 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!

Cozy Studio w/Private entrance & Bathroom
-message me for a custom booking An updated cozy mini suite located in a quiet neighbourhood close to trails & ravines. Low key, budget friendly & overall great value. Outdoor entry allows pure discreetness from others and Personal bathroom gives you all the time you need to get ready. Long term stay for Contract workers, OPG workers, Students & people who need a peaceful getaway. Not ideal for wfh • Ajax / Pickering / Whitby • Condos, suites & apartments •. Student & Contractors

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.

Stunning Lake/CN Tower View: 2BR+2BA, Free Parking
Cozy 2 bedrooms + 2 full baths condo in the heart of downtown tourist hotspot; unobstructed CN tower view; 1 free dedicated parking. Perfect for business or vacation stay! WALKING DISTANCE to: • Supermarket & LCBO: 1 min • Scotiabank Arena: 3 min • Union Station: 3 min • Convention Center: 3 min • Ripley's Aquarium: 3 min • UPX Train: 5 min • Harborfront: 5 min • CN Tower: 5 min • Rogers Center: 7 min • Roy Thompson Hall: 9 min • Royal Alexander Theater: 12 min • St. Lawrence's Market: 18 min

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

Designer sky-high condo w skyline view (pool/gym!)
Amazing light-filled 1-bedroom condo overlooking the centre core of downtown Toronto. Huge windows give you spectacular views of the Rogers Centre, the CN Tower, the Steamwhistle Roundhouse, and the Metro Toronto Convention Centre. Located just steps from the Scotiabank Centre, Rogers Centre, Ripley's Aquarium, and all downtown restaurants and attractions; minutes to walk to any building in the financial core and right at the waterfront. Steps away from Union Station for quick metro access.

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.

Modern Downtown Unionville Stay
Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

Luxury Penthouse | Skyline Views | Markham
Experience luxury living in this top-floor penthouse in Downtown Markham. Relax on the large private balcony with breathtaking skyline views and beautiful changing skies. This spacious 2-bedroom + den, 2-bath suite includes dedicated parking and is ideal for families, business travellers, and extended stays. Steps from Cineplex, restaurants, cafés, Whole Foods, shopping, and the Markham Marriott. Enjoy convenient access to GO Transit and Highways 404 & 407. Hosted by a Superhost.

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

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.

2Bd 2Bath W Stunning View 68%OFF Monthly StepTo CN
This is a fully Furnished 2 BED + 2FULL BATH. CORNER UNIT FREE Parking included/Full kichen WITH all you need to cook... 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
Popular amenities for Pickering condo rentals
Weekly condo rentals

Stylish Urban Condominium STR-2308-JDYBHz

Charming Bowmanville Getaway | Quiet & Comfy

Sunset Retreat | 2BR/2BA | CN Tower View + Parking

Modern 2BR Retreat · Free Parking

Spa Retreat | Sauna & Cold Plunge | Subway to DT

High Landing Luxury Apartment

Waterfront Condo | Lakeview Escape | Free Parking

Luxury 1+Den w/ Parking | Downtown Toronto
Pet-friendly condo rentals

Modern 1BR Toronto Downtown Condo, King size bed

The Beaches pied-á-terre (Woodbine Beach)

College Park :2Bd+2bth + Free parking

Humber Bay Family Friendly condo w Terrace&Parking

Rooftop Pool Condo with CN Tower View

Bright & Cozy Condo w/ Private Balcony - Ent. Dist

Heart of TO, Entertainment & Financial districts

Cozy Condo • Free Parking• Steps from the CN Tower
Condo rentals with a pool

Downtown Markham Unionville

Luxury Downtown Condo For 6 (CN Tower View)

Luxury Downtown Condo For 6 (Near CN Tower)

Toronto CN Tower 2 Bed 2 B w Master King w Parking

Stylish 1BR on Toronto’s Harbourfront

Stylish Downtown Toronto Condo + Free Parking

1BR+Den|Parking&Pool|UnionStation|CNTower&Arena

Luxury CN Tower View, 2BR, Free Parking
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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
- Enercare Centre
- Coca Cola Coliseum
- Massey Hall
- Vaughan Mills





