
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!
ValueFamilyView
4.94 out of 5 average rating, 116 reviews
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
ValueFamilyNearby
4.85 out of 5 average rating, 205 reviews
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.
ValueLocationDecor
4.94 out of 5 average rating, 129 reviews
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
ValueFamilyLaundry
4.95 out of 5 average rating, 634 reviews
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
FamilyLocationLong stay
4.99 out of 5 average rating, 167 reviews
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.
ValueLocationAmenities
4.88 out of 5 average rating, 292 reviews
Stylish Condo Downtown by Rogers Centre
Welcome to our stylish 1-bedroom condo nestled in the heart of downtown Toronto! Our place offers the perfect retreat for couples, solo adventurers, and business travelers seeking a comfortable and convenient stay in the city. Step outside, and you'll be just moments away from plenty of dining options, trendy cafes, shopping boutiques, and exciting nightlife venues. Explore the famous Yonge-Dundas Square, visit the nearby iconic CN Tower, or take a stroll along the picturesque Harbourfront.
LocationFamilyCondition
4.94 out of 5 average rating, 206 reviews
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.
ValueLocationPets
4.9 out of 5 average rating, 169 reviews
Chic Condo Studio w Patio in Heart of Downtown
Cozy & modern condo studio close to Eaton Center, Dundas Square, Ed Mirvish theatre, Massey Hall, City Hall, TMU, Sickkids hospital, St. Michael's hospital, St. Lawrence Market, Art Galleries, fashion stores Streetcar right below the building, Dundas & Queens subway stations mins away take you around the city Restaurant, bar, supermarket, coffee shop all around Fully equipped, high speed internet, unique quiet private space in downtownToronto make a comfy home during your stay
LocationValueAmenities
4.95 out of 5 average rating, 176 reviews
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
ValueFamilyBathroom
4.96 out of 5 average rating, 194 reviews
Charming Downtown Condo in Entertainment District
This is a very spacious condo unit with very efficient and private layout. It has very nice finishes and quality in the Tridel complex right in the heart of the city on Blue Jays Way. Please inquire about possible spot availability in the underground parking. Just about everything is within walking distance of this apartment. That includes sporting stadiums and event spaces, plus shops, restaurants, and cinemas. It's also near the Convention Center, Skydome, and the CN Tower.
LocationFamilyBathroom
4.85 out of 5 average rating, 267 reviews
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.
LocationValueHeating
4.96 out of 5 average rating, 111 reviewsPopular amenities for Pickering condo rentals
Weekly condo rentals

Vibrant downtown place
FamilyLocationCheckout
4.92 out of 5 average rating, 273 reviews
Flowers Falls Hideaway | Modern 2BR Condo Escape
ValueFamilyParking
4.85 out of 5 average rating, 71 reviews
Cozy Studio w/Private entrance & Bathroom
ValueLocationHospitality
4.89 out of 5 average rating, 18 reviews
Modern Downtown Unionville Stay
ValueLocationParks
4.87 out of 5 average rating, 55 reviews
Luxury Penthouse | Skyline Views | Markham
FamilyValueQuiet
4.91 out of 5 average rating, 66 reviews
Scarborough | Parking | HWY401 access | Zoo & UofT
ValueFamilyIndoor spaces
4.89 out of 5 average rating, 27 reviews
Luxury High Rise Living Parking, Gym, Pool, View
FamilyValueAmenities
4.92 out of 5 average rating, 53 reviews
Stylish Urban Condominium STR-2308-JDYBHz
ValueFamilyHospitality
4.93 out of 5 average rating, 88 reviewsPet-friendly condo rentals

The Beaches pied-á-terre (Woodbine Beach)
ValueFamilyComfort
4.9 out of 5 average rating, 152 reviews
Charming Condo w Parking, CN Tower View & Pool
LocationValueLaundry
4.94 out of 5 average rating, 150 reviews
Modern 1BR Toronto Downtown Condo, King size bed
ValueFamilyComfort
4.95 out of 5 average rating, 117 reviews
Humber Bay Family Friendly condo w Terrace&Parking
LocationValueDecor
4.82 out of 5 average rating, 122 reviews
Stylish Apartment in Toronto - Long term available
LocationFamilyLaundry
4.88 out of 5 average rating, 129 reviews
Bright & Cozy Condo w/ Private Balcony - Ent. Dist
ValueLocationCondition
4.89 out of 5 average rating, 134 reviews
Trendy & Cozy 1BD Condo in the Heart of Toronto
LocationValueGetting around
4.86 out of 5 average rating, 145 reviews
Fort York- Lake View Studio Condo + Indoor Parking
LocationValueParks
4.98 out of 5 average rating, 111 reviewsCondo rentals with a pool

Luxury Downtown Condo For 6 (CN Tower View)
LocationFamilyKitchen
4.98 out of 5 average rating, 129 reviews
Prime location • Amazing views • FREE parking
FamilyLocationCleanliness
4.96 out of 5 average rating, 101 reviews
Luxury Downtown Condo For 6 (Near CN Tower)
FamilyLocationCheckout
4.97 out of 5 average rating, 192 reviews
Stylish Downtown Toronto Condo + Free Parking
FamilyLocationSleep quality
4.98 out of 5 average rating, 225 reviews
Modern 2BR 2BATH Urban Core Hotel-Style Condo
LocationValueDecor
4.97 out of 5 average rating, 108 reviews
Stylish 1BR on Toronto’s Harbourfront
LocationValueCheck-in
4.93 out of 5 average rating, 126 reviews
1BR+Den|Parking&Pool|UnionStation|CNTower&Arena
LocationValueHot tub
4.91 out of 5 average rating, 139 reviews
3BR Penthouse with Panoramic Views + Large Terrace
LocationValueGetting around
4.89 out of 5 average rating, 119 reviewsDestinations to explore
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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





