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Condo holiday rentals in Pickering

Find and book unique condos on Airbnb

Quick stats about condo rentals in Pickering

  • Total holiday rentals

    Explore 10 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Wi-Fi availability

    10 of Pickering holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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 favourite
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
4.94 out of 5 average rating, 116 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!

Guest favourite
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
4.85 out of 5 average rating, 205 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

Top Guest favourite
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
4.97 out of 5 average rating, 192 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

Enjoy our luxury 3 bedroom [2 queen 1 double bed], 2 bathroom condo, located in the heart of the Entertainment District. The condo is a short walk to many of the city’s most exciting attractions - CN Tower, Rogers Centre, Scotiabank arena, & the Metro Convention Centre. There is plenty of shopping, fine dining and entertainment in the surrounding areas accessible by foot. For our guests pleasure we have designed the condo to be modern, stylish, and relaxing. We look forward to hosting you!

Top Guest favourite
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
4.94 out of 5 average rating, 126 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.

Guest favourite
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
4.95 out of 5 average rating, 115 reviews

Modern 1BR Toronto Downtown Condo, King size bed

Located in the heart of downtown, this new modern and stylish 1 bedroom condo will be the perfect stay for your next Toronto experience. It features an open concept which blends functionality and comfort, it has soaring ceilings and floor-to-ceiling window. All major attractions and arenas are walking distance to where you will be staying. Events at, Roger’s centre, CN Tower, Ripley’s Aquarium, the Exhibition place, Scotiabank Arena, TIFF lightbox and Waterfront activities are a few mins away.

Guest favourite
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
4.95 out of 5 average rating, 633 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

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
5.0 out of 5 average rating, 164 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

Guest favourite
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
4.91 out of 5 average rating, 161 reviews

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.

Guest favourite
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
4.9 out of 5 average rating, 168 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.

Top Guest favourite
Condo in Downtown Toronto
4.96 out of 5 average rating, 193 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

Top Guest favourite
The image captures the exterior of the Rogers Centre, characterized by its distinct dome structure and large, prominent signage. The CN Tower rises nearby, set against a clear blue sky, highlighting the proximity of this landmark to the condominium.
Condo in Downtown Toronto
4.99 out of 5 average rating, 222 reviews

John-Peter Toronto

Fully furnished 800 sqft (74 m2) two-bedroom condominium located in the heart of downtown Toronto; steps away from Toronto’s main landmarks: ⦁ CN Tower ⦁ Union Station ⦁ Metro Toronto Convention Centre ⦁ Rogers Centre & Scotiabank Arena About the space: 1. Queen bed in the master bedroom 2. Second bedroom has 2 beds 3. Sofa bed in the living room 4. Extra foldable mattress (upon request) 5. Baby crib (upon request) 6. FREE Underground PARKING

Guest favourite
Condo in Downtown Toronto
4.79 out of 5 average rating, 190 reviews

DownTown2Bd 2Bath W Stunning View 65%OFF Step ToCN

This is a fully furnished 2 BED + 2FULL BATH. CORNER UNIT Free Parking included/Full kichen WITH Greatest Balcony with View of the CN Tower and Rogers Centre. Scotia arena .Aquarium Ripleys, Lake,Union Station ,MTCC Only 2 min walk to All above+15 min Walk to museium + City Hall+ Eaton Center Mall +path to longoes+star+Lcbo Starbox+scotia arina+tens of other places and fine resturants. Highlights: → Secured building access with 24/7 concierge

Popular amenities for Pickering condo rentals