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 $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Wifi availability

    10 of Pickering vacation rentals include wifi 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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Superhost
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
4.93 out of 5 average rating, 107 reviews

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!

Superhost
Condo in Ajax
4.82 out of 5 average rating, 11 reviews

Cozy Studio w/Private entrance & Personal Parking

~Message for custom bookings~ An updated cozy mini suite located in a quiet neighbourhood close to trails & ravines. Outdoor entry allows pure privacy from others. Low key, budget friendly & overall great value. Long term stay for Contract workers, OPG workers, Students & people who need a peaceful getaway. Not ideal for wfh or day time sleep • Ajax / Pickering / Whitby • Condos, suites & apartments •. Business traveler • Restaurants, Grocery, Casino & Gas • World Cup

Top guest favourite
Condo in Downtown Toronto
4.96 out of 5 average rating, 170 reviews

Beautiful Petit Gem Ap. In Downtown! Walk Anywhere

Welcome to our lovely petit aparment in heart of downtown Toronto! Our place has everything you might need in order to enjoy the city, work remotely and have a great time when the weather outside is not the best! Located right in downtown, you can basically walk anywere fast: Eaton Centre, Dundas Square, U Toronta, etc. Enjoy many of the high end stores located in the area and also some of the best restaurants! The entire place is sensitized using UV lights and COVID 19 cleaning solutions.

Top guest favourite
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
5 out of 5 average rating, 149 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

Top guest favourite
A bright living and dining area features floor-to-ceiling windows offering expansive views of the city. A modern dining table is surrounded by stylish chairs, while a cozy seating arrangement invites relaxation. Potted plants add a touch of greenery, complementing the contemporary decor.
Condo in Downtown Toronto
4.99 out of 5 average rating, 137 reviews

Million Dollar Views, Free Parking, WiFi

Wake up to stunning views of Toronto Island and the CN Tower! Prepare a delicious meal in our fully-equipped kitchen, and relax by the fire or on your private enclosed balcony. This elegant 2 Bedrooms + 2 Bath offers free parking and is located in the heart of downtown next to Scotiabank Arena and Union Station. Walk to the CN Tower, Rogers Center, Ripley’s Aquarium, and the best restaurants in the city. Promotions available for long term renters. Please message. License# STR-2209-HZZVHM

Top guest favourite
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
4.96 out of 5 average rating, 181 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.

Guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 102 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.

Top guest favourite
The living area features a comfortable gray sofa adorned with decorative pillows, complemented by a sleek coffee table. A large black screen provides an entertainment option, while a floor lamp offers additional lighting. Expansive windows frame outdoor views, illuminating the space with natural light.
Condo in Unionville
4.96 out of 5 average rating, 96 reviews

Cozy Suite in DT Markham Core

One of a kind, luxurious entire condo suite with unobstructed views located in the heart of Downtown Markham. First and only condo with underground access to Marriott Hotel amenities. Unwind with some soft bed sheets, fresh towels, toiletries, shared pool and jacuzzi. This suite includes one private parking space and an office den with high speed internet. Close to bus routes, GO Station, HWY 407 and 404. Steps to VIP Cineplex Theatre, restaurants, bars, parks and more!

Superhost
A modern living space features a light-colored sofa adorned with decorative pillows. A coffee table with various items sits in front of a wall-mounted television. Large windows allow natural light to fill the area, showcasing views of the city beyond.
Condo in Downtown Toronto
4.92 out of 5 average rating, 145 reviews

Luxury Entire Condo At Downtown+parking

Escape to luxury in our 1-bedroom Toronto haven! Enjoy just 5 minute walk to CN Tower and Roger center and 5 minutes ride from billy bishop airport Nestled in a prime Downtown Toronto area, our home boasts luxury furnishings for our guests. Perfect place for your events . Enjoy the seamless blend of comfort and convenience with easy access to highways and the subway and street cars. Unwind in the expansive, Spectacular Views, Comfort and Entertainment.

Guest favourite
A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.
Condo in Mississauga
4.85 out of 5 average rating, 264 reviews

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

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 swimming pool and gym. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Guest favourite
A balcony view showcases the Toronto skyline, featuring the CN Tower amidst a backdrop of modern skyscrapers. The glass railing adds to the open feel, while a pair of woven chairs offers a comfortable seating area to enjoy the cityscape.
Condo in Downtown Toronto
4.95 out of 5 average rating, 149 reviews

Downtown Toronto Penthouse (CN Tower View)

Experience the heart of Downtown Toronto! This modern penthouse features stunning city views and floor-to-ceiling windows filled with natural light. Steps from top restaurants, nightlife, and transit, it’s the perfect base for business or leisure. Paid parking is available next door. A building form with ID, email, and phone number must be completed before check-in.

Top guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 249 reviews

Stylish Studio Steps to Eaton Centre

Centrally located at Yonge-Dundas Square within the 4-Star Pantages Hotel, you will be only steps away from everything Toronto has to offer. This unit is right by the Eaton Centre and Yonge-Dundas Square. Less than a 3-min walk to two subway stations (Queen Station and Dundas Station), street car stops, countless restaurants and cafes, and much more.

Popular amenities for Pickering condo rentals

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