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Condo vacation rentals in Pickering

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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, 116 reviews
Top 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

4.85 out of 5 average rating, 206 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, 130 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

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

4.99 out of 5 average rating, 168 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.

4.88 out of 5 average rating, 293 reviews
Guest favorite
A bright living room features large floor-to-ceiling windows allowing natural light to fill the space. A comfortable gray sectional sofa is paired with a glass coffee table, and a television is mounted on the wall opposite. A neutral area rug adds warmth to the wooden floor.
Condo in Downtown Toronto

Cozy Toronto condo, great location, 1 free parking

Enjoy this conveniently located condo in the entertainment district of downtown Toronto, perfect for outings and group trips with family and friends. 2 Bdrm condo very close to the Lakeshore Waterfront. Short walk to The Rogers Centre, the CN Tower, The Well and Ripley's aquarium. Restaurants are just steps away with King and Queen west walking distance from your stay which is the hub for fine dining and nightlife. For the kids, Ripley's Aquarium, Hockey Hall of fame, Fort York and much more.

4.91 out of 5 average rating, 161 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.

4.94 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.

4.9 out of 5 average rating, 170 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 Relaxing Patio by Yonge Dundas

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

4.95 out of 5 average rating, 177 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, 194 reviews
Guest favorite
A glass table is positioned near large windows, offering an unobstructed view of the city skyline. Two modern chairs are placed around the table, with a small potted plant and a decorative item enhancing the scene. The background features tall buildings and hints of greenery.
Condo in Yorkville

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

4.88 out of 5 average rating, 185 reviews

Popular amenities for Pickering condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Top guest favorite
Condo in Downtown Toronto

Luxury 1BR- Exclusive Maple Leaf Square condo

4.98 out of 5 average rating, 169 reviews
Superhost
Condo in Pickering

Flowers Falls Hideaway | Modern 2BR Condo Escape

4.85 out of 5 average rating, 72 reviews
Guest favorite
Condo in Ajax

Cozy Studio w/Private entrance & Personal Bathroom

4.89 out of 5 average rating, 19 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

4.87 out of 5 average rating, 55 reviews
Superhost
Condo in Scarborough

Scarborough | Parking | HWY401 access | Zoo & UofT

4.89 out of 5 average rating, 28 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, 66 reviews
Guest favorite
Condo in Scarborough

Luxury High Rise Living Parking, Gym, Pool, View

4.92 out of 5 average rating, 53 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, 88 reviews

Pet-friendly condo rentals

Guest favorite
Condo in Downtown Toronto

Debonair Condo Heart of Toronto w/Free Parking

4.96 out of 5 average rating, 112 reviews
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, 153 reviews
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, 117 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

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

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

4.89 out of 5 average rating, 134 reviews
Guest favorite
A rooftop pool reflects the blue sky while providing views of the CN Tower and surrounding modern buildings. Lounge chairs are positioned beside the pool, creating a relaxed atmosphere. The clear water invites enjoyment against the urban backdrop.
Condo in Downtown Toronto

Rooftop Pool Condo with CN Tower View

4.94 out of 5 average rating, 179 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, 129 reviews
Top guest favorite
A bright bedroom features a spacious bed adorned with plush pillows in pink stripes. Large windows provide stunning views of the cityscape, while dark curtains offer options for privacy and light control.
Condo in Yorkville

Admire City Views from Bed at this Chic Apartment

5.0 out of 5 average rating, 200 reviews

Condo rentals with a pool

Top guest favorite
Condo in Downtown Toronto

Luxury Downtown Condo For 6 (CN Tower View)

4.98 out of 5 average rating, 130 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

4.96 out of 5 average rating, 102 reviews
Superhost
The image captures a vibrant urban landscape featuring a modern building with glass and metal elements. The prominent CN Tower stands in the background against a clear blue sky. The area is filled with pedestrians enjoying the surroundings, complemented by greenery and architectural structures.
Condo in Downtown Toronto

Central downtown condo next2 CNtower+free parking

4.85 out of 5 average rating, 106 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, 192 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, 109 reviews
Top guest favorite
Condo in Downtown Toronto

Stylish Downtown Toronto Condo + Free Parking

4.98 out of 5 average rating, 225 reviews
Superhost
A bright living area features a modern orange sectional sofa and a wooden coffee table. Large windows offer views of the cityscape. A dining area with high chairs is positioned beside a compact kitchen, with red cabinetry adding a pop of color.
Condo in Downtown Toronto

Beautiful Condo Across CN Tower and MTCC

4.84 out of 5 average rating, 167 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

4.92 out of 5 average rating, 142 reviews

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