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.

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Guest favorite
A modern living area features a deep blue accent wall with geometric designs. A comfortable brown sofa faces a sleek coffee table, complemented by a nearby dining set. Large windows provide a bright view of the outdoors, allowing ample natural light to enter the space.
Condo in Scarborough

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
Guest favorite
A balcony view captures the iconic CN Tower alongside a modern building structure. The expansive glass windows reflect the urban skyline and lake in the distance, evoking a sense of openness and connection to the city.
Condo in Downtown Toronto

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
Top guest favorite
A comfortable living area is presented with a light-colored sectional sofa and a brown leather armchair. A modern entertainment unit displays a flat-screen television, complemented by framed artwork on the walls. A soft area rug partially covers the wooden floor, enhancing the inviting atmosphere.
Condo in Downtown Toronto

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
Top guest favorite
The image displays the CN Tower from different angles, showcasing its height against a sunset and nighttime sky. The left view highlights the tower with the Rogers Centre below, while the right view features the illuminated tower amidst the city lights, emphasizing the vibrant colors at night.
Condo in Downtown Toronto

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
Top guest favorite
A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.
Condo in Yorkdale

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
Guest favorite
The living area features a black leather sofa with decorative cushions, accompanied by a natural wood coffee table and a black chair. Two lamps provide soft lighting, and large windows offer expansive views of the downtown skyline.
Condo in Downtown Toronto

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
Guest favorite
A well-lit living area features a gray pull-out sofa and a coffee table atop a patterned area rug. Large windows offer expansive views of the cityscape, while a potted plant adds a touch of greenery. A wall art piece adorns the light blue wall.
Condo in Downtown Toronto

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
Guest favorite
A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.
Condo in Mississauga

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
Top guest favorite
A modern bedroom is furnished with a spacious wooden bed adorned with plush pillows and a soft blanket. A nightstand holds a sleek lamp, while a large window allows natural light to enhance the room's calming atmosphere. Colorful artwork decorates the wall, adding visual interest.
Condo in Downtown Toronto

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
Top guest favorite
Condo in Downtown Toronto

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
Guest favorite
Condo in Downtown Toronto

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
Guest favorite
Condo in Downtown Toronto

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 reviews

Popular amenities for Pickering condo rentals

Pet-friendly condo rentals

Condo rentals with a pool

Top guest favorite
Condo in Downtown Toronto

Luxury Downtown Condo For 6 (CN Tower View)

LocationFamilyKitchen

4.98 out of 5 average rating, 129 reviews
Guest favorite
A living area features two brown leather sofas positioned near large windows, offering a view of the downtown skyline. A floor lamp stands beside a decorative bench, and two floral paintings adorn the wall, adding a touch of elegance to the modern space.
Condo in Downtown Toronto

Prime location • Amazing views • FREE parking

FamilyLocationCleanliness

4.96 out of 5 average rating, 101 reviews
Top guest favorite
A light-filled bedroom features a spacious bed dressed in crisp white linens. Two bedside tables with lamps stand on either side. A large window provides a glimpse of the city outside, complemented by a decorative indoor plant and modern wall art.
Condo in Downtown Toronto

Luxury Downtown Condo For 6 (Near CN Tower)

FamilyLocationCheckout

4.97 out of 5 average rating, 192 reviews
Top guest favorite
Condo in Downtown Toronto

Stylish Downtown Toronto Condo + Free Parking

FamilyLocationSleep quality

4.98 out of 5 average rating, 225 reviews
Top guest favorite
An open-concept living space features a modern kitchen with dark wood cabinetry and red accents. A dining table with stylish chairs is positioned beside a cozy seating area, while floor-to-ceiling windows allow natural light to fill the room, offering a view of the vibrant city.
Condo in Downtown Toronto

Modern 2BR 2BATH Urban Core Hotel-Style Condo

LocationValueDecor

4.97 out of 5 average rating, 108 reviews
Guest favorite
A bright living space showcases a comfortable sofa beside a round glass table. A large TV is mounted on a textured wall. Natural light floods in from floor-to-ceiling windows, revealing city views, while a cozy bedroom is visible through an open doorway.
Condo in Downtown Toronto

Stylish 1BR on Toronto’s Harbourfront

LocationValueCheck-in

4.93 out of 5 average rating, 126 reviews
Guest favorite
The living area features a white leather sofa adorned with blue floral cushions, paired with a glass coffee table. A plant is positioned beside the floor-to-ceiling windows, allowing natural light to brighten the space. In the background, the kitchen is visible with modern appliances.
Condo in Downtown Toronto

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

LocationValueHot tub

4.91 out of 5 average rating, 139 reviews
Guest favorite
A modern living area is highlighted by large windows offering views of the outside. A spacious sectional sofa is complemented by decorative cushions. A sleek kitchen island with stone countertops provides ample space, and a dining area is visible, accented by natural light.
Condo in Downtown Toronto

3BR Penthouse with Panoramic Views + Large Terrace

LocationValueGetting around

4.89 out of 5 average rating, 119 reviews