
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.

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.

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.

Sunset Haven
Cozy suite, this location provides the very best of the outdoors for cottaging enthusiasts 45 minutes from the GTA. Found on the outskirts of Port Perry near the Blue Heron Casino and on the shores of Lake Scugog, you will find great fishing, swimming, and boating at your doorstep. Also great lounging on the deck/dock! The casino is 5 min drive and the town of Port Perry with its good restaurants and shopping is 10 min car ride or take your boat! Unfortunately, no pets are allowed by guests.

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.

Lakeside Guest Suite, on Lake Scugog, Port Perry
WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

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!

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.

Beach House: First Floor
Have fun with the whole family at this stylish place. It's a beach side custom made luxury house where you can enjoy sunrise and sun set view with Bar, Restaurant, Park, Public transport, Shopping Mall and many other amenities are just one step away. Its bright, specious and peaceful accommodation.
Popular amenities for waterfront rentals in Pickering
Waterfront apartment rentals

Cozy Entire Apt - Quietness & Privacy

Good Looking Condo Across from CN TOWER & MTCC

Magical Design, next to Toronto & GoTrain

Waterfront Cozy Escape

Amazing Lake View Studio Beside CN Tower

Lake Breeze Apartment, EV Charging & Free Parking

Bright & Spacious Condo | Next to CN Tower

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

New Entire Unit-Upper Beaches w/ Parking & Laundry

Modern Lakefront Cottage In The City With Hot Tub

Chic 1-Bdrm Suite Steps to The Beaches & Boardwalk

Bright Spacious Sun Filled Oasis w/ Parking

Private Suite - Ajax by the Lake

Luxury & Modern Home in Thornhill, Parking, Yard

Daydream Treehouse

Luxury Beaches Home Gourmet Kitchen Private Garden
Waterfront apartment rentals

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

Lux Waterfront Condo by Rogers -IndoorPool-Parking

Lakeside Condo Studio In Downtown Toronto

Luxury Condo with FreeParking. CN Tower Lake View

Luxury Entire Condo At Downtown+parking

Beautiful Lake View Studio Condo + 1 free Parking

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

Downtown Toronto 2 BDR Condo CN Tower/Lake Views
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹4,794 | ₹5,504 | ₹5,682 | ₹5,415 | ₹5,682 | ₹6,125 | ₹7,723 | ₹7,280 | ₹6,747 | ₹6,392 | ₹6,303 | ₹5,238 |
| 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 ₹1,776 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
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Capital District, New York Holiday rentals
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Island of Montreal Holiday rentals
- Northeast Ohio Holiday rentals
- Pittsburgh Holiday rentals
- Rentals with breakfast Pickering
- Rentals with pools Pickering
- Rentals with lake access Pickering
- Apartment rentals Pickering
- Rentals with an EV charger Pickering
- Rentals with a firepit Pickering
- Rentals with beach access Pickering
- Rentals with a hot tub Pickering
- Guest house rentals Pickering
- Pet-friendly rentals Pickering
- Rentals with outdoor seating Pickering
- Smoking-friendly rentals Pickering
- Family-friendly rentals Pickering
- Cottage rentals Pickering
- Townhouse rentals Pickering
- Flat rentals Pickering
- Rentals with a washing machine and dryer Pickering
- House rentals Pickering
- Rentals with a fireplace Pickering
- Fitness-friendly rentals Pickering
- Beachfront rentals Pickering
- Rentals with a patio Pickering
- Private suite rentals 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
- Royal Woodbine Golf Club