
Waterfront holiday rentals in Pickering
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Top-rated waterfront rentals in Pickering
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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.

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!

Lakeside Condo Studio In Downtown Toronto
Luxury waterfront condo in Historic Fort York District with amazing amenities. Right by the waterfront LakeOntario and minutes from downtown Toronto. The studio is very clean and contemporary with balcony facing the lake. Walking distance to PorterAirport, ScotiaArena, BMO field,RogerCentre, MolsonAmphitheatre, CNE,OntarioPlace and everything Lakeshore has to offer. Easy access to all of downtown right at your doorstep with 5 min tram ride to UnionStation, UpExpress, GoStation and ViaRail.

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.

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.

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!

Lively 1+1 Lakeview Condo near CN Tower + Free Prk
Enjoy the stunning lake view in this open concept 700 sq ft condo with 9 ft ceilings, in the heart of the harbourfront. Right next to CN Tower, Rogers Centre, and Scotiabank Arena. Includes parking space, TV, and internet. Gym, indoor-out door pool, Variety of restaurants and grocery stores steps away. Minutes walk to subway, Union Station, the business district, and Billy Bishop City Airport.

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.

Good Looking Condo Across from CN TOWER & MTCC
*NO PARTIES OR NONSENSE TOLERATED - VIOLATORS WILL BE FINED UP TO $500 AND EVICTED*** A newly-furnished condo located at the heart of Downtown Toronto guaranteed to maximize your stay with everything at close proximity. This 650 sq ft condo unit has 8 ft ceilings, hardwood flooring , High-speed WiFi, Cable TV, and basic amenities will all be available.
Popular amenities for waterfront rentals in Pickering
Waterfront apartment rentals

Cozy Entire Apt - Quietness & Privacy

Waterfront Cozy Escape

Amazing Lake View Studio Beside CN Tower

Modern 2 Bed Suite + Office - DT Core

Lake Breeze Apartment, EV Charging & Free Parking

Airbnb King & Queen/Wifi/ near Toronto & Casino

Bright & Spacious Condo | Next to CN Tower

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

Luxe, Family Friendly Oasis in Trendy Leslieville!

New Entire Unit-Upper Beaches w/ Parking & Laundry

5 Star Rated & Top 5% Home, Spacious 2bedroom 3bed

Bright Spacious Sun Filled Oasis w/ Parking

Chic 1-Bdrm Suite Steps to The Beaches & Boardwalk

Private Suite - Ajax by the Lake

Daydream Treehouse

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

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

Humber Bay Family Friendly condo w Terrace&Parking

Luxury Condo with FreeParking. CN Tower Lake View

3 Bedroom CN Tower Waterfront Oasis

Beautiful Lake View Studio Condo + 1 free Parking

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

Luxury 3BR Sky Condo - Award Winning Design

Modern High-Floor Luxury w/ Balcony, Near CN Tower
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $70 SGD | $81 SGD | $83 SGD | $79 SGD | $83 SGD | $90 SGD | $109 SGD | $117 SGD | $112 SGD | $94 SGD | $92 SGD | $77 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 2,170 verified reviews to help you choose

Family-friendly holiday rentals
30 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
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
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- Flat rentals Pickering
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- Rentals with beach access Pickering
- Rentals with a patio Pickering
- Pet-friendly rentals Pickering
- Cottage rentals Pickering
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- Rentals with a fireplace Pickering
- Smoking-friendly rentals Pickering
- Waterfront rentals Durham Region
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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
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- CF Toronto Eaton Centre
- Financial District
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Christie Pits Park
- Toronto City Hall
- Royal Woodbine Golf Club
- Jackson-Triggs Niagara Estate




