Waterfront holiday rentals in Pickering

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Top-rated waterfront accommodation in Pickering

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern living area is highlighted by large windows allowing natural light. A sleek black sectional couch faces a glass coffee table, while a light-colored armchair adds comfort. A wall-mounted TV is positioned for viewing, contributing to a relaxed atmosphere.
Condo in Entertainment District
4.96 out of 5 average rating, 156 reviews

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)

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, 121 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
The spacious living area features a comfortable sectional sofa, a glass coffee table, and a large smart TV positioned for easy viewing. Decorative art and plants enhance the ambiance, while a dining table for two is visible in the background, creating a functional and inviting space.
Condo in Harbourfront
4.91 out of 5 average rating, 197 reviews

FIFA Location! Sleek 40+ Floor with CN Tower View

Step into the modern and stylish 1BR 1Bath condo on the 40th+ floor in the very heart of Downtown Toronto. It promises stunning panoramic views of CN Tower, Rogers Center, the picturesque lake, and much more. Explore the city before retreating to this gorgeous gem whose million-dollar views and rich amenity list will leave you in awe. ✔ Panoramic City & Lake View ✔ Comfortable Bedroom ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer See more below!

Top Guest favourite
A modern living area is presented with a cozy grey sofa adorned with decorative pillows. A glass table is set with a vase of flowers, complemented by a green accent chair. Natural light filters in through large sliding doors, leading to a balcony.
Condo in Entertainment District
4.93 out of 5 average rating, 168 reviews

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.

Top Guest favourite
A spacious living room is depicted, featuring a light-colored sofa with decorative cushions and a woven throw. A coffee table with a marble-like surface sits in front, alongside a side table supporting a modern lamp. Soft lighting enhances the welcoming ambiance.
Guest suite in Brampton
4.94 out of 5 average rating, 126 reviews

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.

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.
Apartment in Richmond Hill
4.96 out of 5 average rating, 405 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 tranquil view of a lake reflects the colorful hues of the sunset, with a modern building nestled among trees on the opposite shore. The surrounding landscape features gentle slopes leading to the water, creating a peaceful natural setting.
Guest suite in Newcastle
4.91 out of 5 average rating, 244 reviews

Romantic Nature Retreat - Hydrotherapy Suite

A Romantic Retreat, located on 91 acres, beside a small, spring-fed lake, this is a private hydrotherapy suite with its own sitting area and firepit, providing a relaxing getaway close to the city. Gentle walking trails and abundant wildlife around the lake Swimming, dock, canoe & paddleboat Ideal for two people, 2SLGBTQ+ all welcome 6 min drive to Newcastle for dinner, shopping... Please read reviews & full ad before booking. Pets are welcome.

Guest favourite
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, 219 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 spacious living area featuring a comfortable gray sofa and a modern TV set. A dining table is set for four, accompanied by light wood chairs. Large windows allow natural light to fill the room, complemented by soft gray curtains. A tall indoor plant adds a touch of greenery.
Apartment in Entertainment District
4.92 out of 5 average rating, 159 reviews

2BR 2 Bath Condo Across 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 750 sq ft condo unit has 9 ft ceilings, hardwood flooring, High-speed WiFi, Cable TV, washing machine/dryer, and basic amenities will all be available.

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.
Apartment in Port Perry
4.98 out of 5 average rating, 185 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.

Popular amenities for Pickering waterfront rentals

When is the best time to visit Pickering?

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Avg. price$90 NZD$103 NZD$106 NZD$101 NZD$106 NZD$115 NZD$140 NZD$150 NZD$143 NZD$120 NZD$118 NZD$98 NZD
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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 $33 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Pickering holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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