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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 162 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!

4.94 out of 5 average rating, 114 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

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.

4.89 out of 5 average rating, 115 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.

4.94 out of 5 average rating, 124 reviews
Top guest favorite
Condo in Downtown Toronto

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.

4.98 out of 5 average rating, 129 reviews
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

4.95 out of 5 average rating, 632 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

5.0 out of 5 average rating, 161 reviews
Top guest favorite
A modern living area features a grey sectional sofa paired with a wooden coffee table. Natural light streams through large windows, revealing a view of the city. A 55-inch Smart TV is positioned on a dark wood console, complemented by decorative elements on the table.
Condo in Downtown Toronto

Charming Condo w Parking, CN Tower View & Pool

Enjoy your stay at a charming & modern condo located in the heart of downtown Toronto. Stop settling for sub-par accommodations, and treat yourself to this fully equipped, meticulously cleaned unit with 1 Queen Bed + 1 Sofa Bed. You will be within steps (literally) to the CN Tower, Rogers Center, Ripley’s, and many of Toronto’s top attractions. I am an extremely passionate & attentive host who will cater to your requests and desires. Shoot me a message to get started on your Toronto getaway.

4.94 out of 5 average rating, 148 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.

4.95 out of 5 average rating, 201 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.

4.9 out of 5 average rating, 167 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

4.96 out of 5 average rating, 192 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.

4.96 out of 5 average rating, 110 reviews
Top guest favorite
A modern living area features a spacious, cozy sectional sofa with decorative pillows. A large window offers views of the city skyline and access to a balcony adorned with patio furniture. Natural light fills the room, complementing the contemporary decor and wooden flooring.
Condo in Liberty Village

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.

4.98 out of 5 average rating, 145 reviews

Popular amenities for Pickering condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Superhost
Condo in Mississauga

Square-One Condo Amazing View (accommodates 6)

4.83 out of 5 average rating, 195 reviews
Superhost
Condo in Pickering

Flowers Falls Hideaway | Modern 2BR Condo Escape

4.84 out of 5 average rating, 70 reviews
Superhost
Condo in Ajax

Cozy Studio w/Private entrance & Personal Parking

4.85 out of 5 average rating, 13 reviews
Guest favorite
A modern living area features a light-colored sectional sofa and a coordinating accent chair, complemented by a round glass coffee table. Floor-to-ceiling windows provide unobstructed views of the landscape, allowing for ample natural light. Decorative art pieces enhance the stylish ambiance of the space.
Condo in Unionville

Luxury Penthouse | Skyline Views | Markham

4.91 out of 5 average rating, 65 reviews
Guest favorite
A modern living area features a sleek kitchen equipped with stainless steel appliances, including a microwave and oven. A comfortable sofa is positioned beside a large window, offering natural light. A breakfast bar with stools enhances the inviting space, which includes a neutral-toned area rug.
Condo in Unionville

Modern Downtown Unionville Stay

4.89 out of 5 average rating, 53 reviews
Superhost
Condo in Scarborough

Scarborough | Parking | HWY401 access | Zoo & UofT

4.88 out of 5 average rating, 26 reviews
Guest favorite
A modern kitchen area is equipped with stainless steel appliances, including a refrigerator and an oven. A compact dining table is positioned next to the sleek couch in the living area, which is well-lit by natural light coming through the large window.
Condo in Bowmanville

Charming Bowmanville Getaway | Quiet & Comfy

4.84 out of 5 average rating, 70 reviews
Guest favorite
The entrance to the building is framed by vibrant flowers in planters. A set of stone steps leads up to large glass doors, which are flanked by modern wall lights. Metal handrails provide support on both sides of the steps.
Condo in Toronto

Stylish Urban Condominium STR-2308-JDYBHz

4.93 out of 5 average rating, 84 reviews

Pet-friendly condo rentals

Guest favorite
An open living area is visible, featuring a dark sofa and a wooden dining table set for four. A wall-mounted television is located opposite the sofa, while large floor-to-ceiling windows allow natural light to brighten the space, accented by sheer curtains.
Condo in Downtown Toronto

Modern 1BR Toronto Downtown Condo, King size bed

4.95 out of 5 average rating, 114 reviews
Top guest favorite
An open concept studio features a wall-mounted Murphy bed, ample storage space in white cabinetry, and a kitchenette equipped with modern appliances. A small dining table with two stools is positioned near the kitchenette, while a comfortable sofa is positioned along the wall.
Condo in The Beaches

The Beaches pied-á-terre (Woodbine Beach)

4.9 out of 5 average rating, 151 reviews
Guest favorite
Condo in Downtown Toronto

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

4.88 out of 5 average rating, 130 reviews
Top guest favorite
A cozy living area features a gray sectional sofa adorned with decorative pillows. A round coffee table sits in front, positioned on a patterned rug. Large windows provide natural light and views of the city, with sheer dark curtains on either side.
Condo in Downtown Toronto

Cozy Condo • Free Parking• Steps from the CN Tower

4.98 out of 5 average rating, 100 reviews
Top guest favorite
A modern kitchen area is equipped with stainless steel appliances, including a large refrigerator and oven. A glass-topped breakfast bar is accompanied by two neutral-colored stools. Decorative wall art and a small plant add visual interest, while natural light enhances the bright ambiance.
Condo in Downtown Toronto

Vibrant downtown place

4.92 out of 5 average rating, 270 reviews
Guest favorite
A bright living area is featured with an open-concept layout, showcasing a modern kitchen with sleek appliances and a dining table surrounded by black leather chairs. Floor-to-ceiling windows offer ample natural light, while a cozy seating area provides a welcoming atmosphere.
Condo in Downtown Toronto

College Park :2Bd+2bth + Free parking

4.93 out of 5 average rating, 227 reviews
Superhost
Condo in Downtown Toronto

Luxury 1 Bedroom Condo in Downtown Toronto

4.86 out of 5 average rating, 152 reviews
Guest favorite
A well-appointed bedroom features a queen-sized bed with premium linens and decorative pillows. A terracotta accent wall is complemented by soft lighting from a woven pendant lamp. Two nightstands with lamps sit beside the bed, and a cozy throw blanket rests over the foot of the bed.
Condo in Toronto

Stylish Apartment in Toronto - Long term available

4.88 out of 5 average rating, 128 reviews

Condo rentals with a pool

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

4.93 out of 5 average rating, 123 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)

4.97 out of 5 average rating, 191 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

4.85 out of 5 average rating, 200 reviews
Guest favorite
Condo in Downtown Toronto

BEST LOC Period/ 62% OFF on monthly lease/parking

4.79 out of 5 average rating, 187 reviews
Guest favorite
A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.
Condo in Downtown Toronto

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

4.95 out of 5 average rating, 159 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

4.91 out of 5 average rating, 130 reviews
Guest favorite
Condo in Downtown Toronto

Luxury CN Tower View, 2BR, Free Parking

4.98 out of 5 average rating, 129 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

4.97 out of 5 average rating, 106 reviews

Destinations to explore