
Waterfront vacation 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.

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.

3BR&2BATH Condo CNT+Lake 2mins walk Subway Station
Trust me, this brand new luxurious 3 bedroom 2 bath condo located at Toronto downtown core has some magic to let you enjoy yourself so much as to forget to leave. Experiencing amazing view of CN Tower & Lake Ontario; only a 3-minute walk to TTC Osgoode Station and close to every Toronto's most famous attractions; various Toronto best restaurant, shopping, nightlife, entertainment nearby. Perfect for families, business travelers or a group of good friends. *Not ideal for parties *Must be quite

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.

Bright & Spacious Condo | Next to CN Tower
Welcome to our beautiful condo located in the heart of Toronto's Entertainment District! This cozy unit is located within walking distance from some of Toronto's most popular attractions, restaurants and nightlife, including the CN Tower, Rogers Center, Scotiabank Arena, and Ripley's Aquarium. Whether you're in town for business or pleasure, we're confident you'll love your stay at our cozy and convenient condo. Book your stay today and experience the best of Toronto living!

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.

Chirping-Paradise Glamping Dome
Looking for a quick escape close to the city? Our glamping dome offers a serene retreat on 10 acres of trails, streams, and a peaceful pond. Perfect for birthdays, anniversaries, and family gatherings, it blends nature with a touch of luxury. In winter, enjoy the snowy outdoors and stay warm inside with the wood pellet stove. Thoughtfully designed for comfort and romance, with upscale amenities and fast Wi-Fi, it’s the ideal spot to create unforgettable memories.

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!

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.

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
Waterfront apartment rentals

Cozy Entire Apt - Quietness & Privacy

Good Looking Condo Across from CN TOWER & MTCC

Luxury CN Tower and Lake View Penthouse Sleeps 10

Waterfront Cozy Escape

Oakville Oasis - Free Parking and WiFi

Amazing Lake View Studio Beside CN Tower

Lake Breeze Apartment, EV Charging & Free Parking

Heart of Downtown Modern 1 Bedroom Condo
Waterfront house rentals

New Entire Unit-Upper Beaches w/ Parking & Laundry

Chic 1-Bdrm Suite Steps to The Beaches & Boardwalk

Bright Spacious Sun Filled Oasis w/ Parking

Rated Top 5% of Homes 1500 ft.² 2Bed close to lake

Private Suite - Ajax by the Lake

Daydream Treehouse

Luxury & Modern Home in Thornhill, Parking, Yard

Luxury Beaches Home Gourmet Kitchen Private Garden
Waterfront condo rentals

Lux Waterfront Condo by Rogers -IndoorPool-Parking

Humber Bay Family Friendly condo w Terrace&Parking

Luxury Condo with FreeParking. CN Tower Lake View

3 Bedroom CN Tower Waterfront Oasis

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

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

Luxury 3BR Sky Condo - Award Winning Design

Downtown 1BR+Sofabed/Steps to ScotiabankArena/MTCC
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$11,297 GYD | G$12,971 GYD | G$13,389 GYD | G$12,762 GYD | G$13,389 GYD | G$14,436 GYD | G$18,201 GYD | G$17,155 GYD | G$15,900 GYD | G$15,063 GYD | G$14,854 GYD | G$12,343 GYD |
| 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 vacation rentals
Explore 60 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at G$4,184 GYD per night before taxes and fees

Verified guest reviews
Over 2,170 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Pickering vacation rentals include wi-fi 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 Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Mount Pocono Vacation rentals
- Capital District, New York Vacation rentals
- Niagara Falls Vacation rentals
- Grand River Vacation rentals
- St. Catharines Vacation rentals
- Island of Montreal Vacation rentals
- Northeast Ohio Vacation rentals
- Pittsburgh Vacation rentals
- Rentals with an EV charger Pickering
- Rentals with pools Pickering
- Rentals with breakfast Pickering
- House rentals Pickering
- Apartment rentals Pickering
- Beachfront rentals Pickering
- Rentals with a patio Pickering
- Rentals with outdoor seating Pickering
- Guesthouse rentals Pickering
- Rentals with a hot tub Pickering
- Rentals with a fire pit Pickering
- Family-friendly rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with a fireplace Pickering
- Smoking-friendly rentals Pickering
- Rentals with lake access Pickering
- Rentals with beach access Pickering
- Cottage rentals Pickering
- Townhouse rentals Pickering
- Pet-friendly rentals Pickering
- Condo rentals Pickering
- Private suite rentals Pickering
- Rentals with a washer and dryer Pickering
- Waterfront rentals Durham Region
- Waterfront rentals Ontario
- Waterfront rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Toronto City Hall
- Christie Pits Park
- Jackson-Triggs Niagara Estate