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Waterfront holiday rentals in Pickering

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Pickering

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Top guest favourite
A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.
Cabin in Whitchurch-Stouffville
4.99 out of 5 average rating, 117 reviews

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.

Top guest favourite
A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.
Guest suite in Toronto
4.94 out of 5 average rating, 213 reviews

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.

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.98 out of 5 average rating, 556 reviews

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.

Top guest favourite
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.
Apartment in Fort York
4.97 out of 5 average rating, 139 reviews

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!

Guest favourite
A contemporary waterfront condominium complex is visible, showcasing multiple glass-fronted balconies and lush greenery surrounding the entrance. The building features an urban design with large windows, allowing for abundant natural light, under a vibrant blue sky with scattered clouds.
Apartment in Fort York
4.89 out of 5 average rating, 453 reviews

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.

Top guest favourite
A modern living area is depicted, featuring a dark sofa adorned with decorative pillows and a light wooden coffee table. A circular dining table with white chairs is in the foreground, while a wall-mounted TV is positioned opposite. Warm lighting enhances the spacious feel.
Flat in Richmond Hill
4.96 out of 5 average rating, 398 reviews

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.

Superhost
A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.
Dome in East Gwillimbury
4.9 out of 5 average rating, 251 reviews

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.

Superhost
A modern living space features a light-colored sofa adorned with decorative pillows. A coffee table with various items sits in front of a wall-mounted television. Large windows allow natural light to fill the area, showcasing views of the city beyond.
Apartment in Entertainment District
4.94 out of 5 average rating, 127 reviews

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.

Superhost
A serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.
Guest suite in Pickering
4.8 out of 5 average rating, 216 reviews

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!

Top guest favourite
A small balcony features a bistro table and two wooden chairs, overlooking a serene view of Lake Ontario. A potted plant sits in the center of the table, with the shimmering water and distant shore visible in the background.
Apartment in Harbourfront
4.97 out of 5 average rating, 314 reviews

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.

Top guest favourite
A serene sunset over Lake Scugog is captured, reflecting vibrant hues of orange and purple across the water's surface. Docking spaces are visible in the foreground, framed by a peaceful natural backdrop, enhancing the tranquil outdoor atmosphere.
Flat in Port Perry
4.98 out of 5 average rating, 184 reviews

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.

Superhost
An open-plan living area showcases a round wooden dining table set for four, surrounded by black chairs. A modern kitchen features dark cabinetry and stainless steel appliances. Natural light fills the space through large windows, providing a view of the cityscape.
Flat in Entertainment District
4.83 out of 5 average rating, 114 reviews

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

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
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
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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

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  4. Durham Region
  5. Pickering
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