
Waterfront holiday rentals in Pickering
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Top-rated waterfront rentals in Pickering
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Spacious 1 Bed + Den + Downtown + Free Parking
Spacious 1 bed+den modern condo located in the heart of downtown. Steps from the lake, parks, recreation centers. Short walk to CN Tower, Union Station, Rogers Center, Convention Center. → FAST WIFI Perfect for WFH, video calls, & streaming → Approx size 620ft² / 57m² → Dedicated Working space → 60" QLED TV → *NEW 2024* Fully equipped kitchen w/ set of cookware → Walking distance to dining & night life option → Minutes away from grocery, liquor stores, & city transit network (94 Transit Score)

Lakefront getaway for two on Musselman's Lake
An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

Cozy small newly built Toronto Islands getaway
Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Treehouse on private, isolated forest (300 acres)
You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Modern 1 BR Near CN Tower – 10 Min Walk
Our boutique condo is located in the centre of Toronto. Just steps away from the Entertainment District (King W & Queen W), you'll find restaurants, bars, cafes, and the theatre district just up the street. Enjoy our 1 BR + BA condo with access to all of the amenities during your stays with us, such as the sauna, steam room, gym, and rooftop patio. Experience Toronto with the Lakeshore, Roger's Centre, and Eaton’s Centre, all no more than a 20 minute walk away. 5 minute walk to The Well.

Lux Waterfront Condo Pool Hot Tub Free Parking
This lakeside condo is designed to give you a 5-star experience. Upon entrance you are greeted with champagne and a gift basket! Steps away from the main attractions. Walk to the CN Tower, Scotia Bank Arena, Rogers Centre, Ontario Place, Cinesphere Theatre, Budweiser Stage, Historic Fort York, Billy Bishop Airport (YTZ), BMO Field, and more! Enjoy your 5-star stay with our amenities including an indoor pool, jacuzzi, sauna, odyssey gym (located on the same floor), outdoor roof top hot tub!

Lake Guest Suit> 15 mins YYZ>private whole place
You will enjoy this newly renovated private space! Located on the edge of beautiful Professor's Lake, a walk-out basement apartment with a separate entrance, spacious living room, bright bedroom, jet shower bathroom, comfortable king-size bed and new kitchen. Everything separated from upstairs. Private access to the lakeside path from the backyard. Enjoy your morning breeze from the lake when you walk around the lake. A lot of natural beauties, birds, fishes, turtles and great lake views.

Modern Cozy Home near the Mill Pond Park.
Our newly renovated basement apartment will enchant you with its contemporary style, brightness and coziness (large lookout windows, super bright!). It is fully furnished with style and attention to details so you can feel at home away from home. It is just a few steps away from the beautiful Mill Pond Park - a great place to immerse in the beauty of nature. The park has many lovely trails that you can explore. The apartment has everything you need to make your stay perfect.

Deerleap Glamping Dome
Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Amazing Lake View Studio Beside CN Tower
Experience modern downtown living near the CN Tower, Scotiabank Arena, and the waterfront. This bright, open-concept condo offers a full kitchen, comfortable lounge, and floor-to-ceiling windows. Enjoy free Wi-Fi, fresh linens, and professional cleaning. Perfect for business or leisure, you're steps from top dining, entertainment, and easy transit. Valid ID is required at check-in; quiet hours run 10 p.m.–8 a.m. Book now and enjoy Toronto!

Muskoka on the City
Located in Rouge National Urban Park, steps from a beautiful lake and beach. Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Lake Brews
Welcome to Lake brews, where we are passionate about providing an unprecedented level of hospitality and accommodations for our guests. We love to travel, just like you, and we have drawn from all of our experiences from our stays at resorts around the world in order to create a truly memorable experience for you, here, on Lake Scugog, just an hour drive from the GTA.
Popular amenities for waterfront rentals in Pickering
Waterfront apartment rentals

Cozy Entire Apt - Quietness & Privacy

FIFA Location! All New CN Tower View Condo

Oakville Oasis - Free Parking and WiFi

FIFA location! Newly Furnished CN Tower 2 BR Condo

FIFA Location! New 40th+ floor w View of CN Tower

City Penthouse Suite - GRAND Lake View & Parking

FIFA Location! 45+ Floor Downtown Condo w View

Luxury Condo near CN Tower/Scotia Arena w/ parking
Waterfront house rentals

Luxe Private Family Home Near Downtown Toronto

New Entire Unit-Upper Beaches w/ Parking & Laundry

Beautiful End-unit Townhome with Lakeview Room

Modern Lakefront Cottage In The City With Hot Tub

Bright Spacious Sun Filled Oasis w/ Parking

Relax in Style! | Sophisticated ManCave in the Sky

Private Suite - Ajax by the Lake

Luxury & Modern Home in Thornhill, Parking, Yard
Waterfront apartment rentals

3BR & 2BATH Condo CNT+Lake 2mins walk Subway Station

Luxury Condo with FreeParking. CN Tower Lake View

Beautiful Lake View Studio Condo + 1 free Parking

3 Bedroom CN Tower Waterfront Oasis

FIFA Location! Sleek 40+ Floor with CN Tower View

⭐️KING Bed Luxury Condo - CN Tower View + Parking⭐️

Artsy and Comfy Home with a View

Modern Condo with Balcony Lakeview
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $69 SGD | $80 SGD | $82 SGD | $78 SGD | $82 SGD | $89 SGD | $108 SGD | $116 SGD | $111 SGD | $93 SGD | $91 SGD | $76 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about waterfront rentals in Pickering

Total holiday rentals
Explore 60 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 2,380 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Pickering holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pickering rentals

4.7 Average rating
Pickering stays receive an average rating of 4.7 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Bay Station
- BMO Field
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- York University
- Lakeridge Ski Resort
- Toronto City Hall
- Christie Pits Park
- Rouge National Urban Park




