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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.

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Guest favorite
Condo in Entertainment District
4.95 out of 5 average rating, 153 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 favorite
Cabin in Whitchurch-Stouffville
4.99 out of 5 average rating, 115 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 favorite
Guest suite in Toronto
4.95 out of 5 average rating, 204 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 favorite
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.

Superhost
Cottage in Bowmanville
4.9 out of 5 average rating, 172 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

Top guest favorite
Apartment in Richmond Hill
4.96 out of 5 average rating, 389 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
Dome in East Gwillimbury
4.89 out of 5 average rating, 245 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
Guest suite in Pickering
4.79 out of 5 average rating, 211 reviews

Muskoka on the City

Property situated on Rouge National Urban Park, close to Toronto zoon, seaton trail. step to beautiful lake and beach , you will enjoy hiking,kayak ,bike and fishing.Close to highway,resultant,shopping mall,public transport, Rouge Hill GO Station. bright in ground suite .kitchen ,dinning room in basement with TV, private bathroom(basement), and private entrance(back yard). Suite has a separate bedroom with a queen sized bed, free wireless internet, and full laundry.

Top guest favorite
Apartment in Port Perry
4.98 out of 5 average rating, 180 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
Apartment in Entertainment District
4.84 out of 5 average rating, 109 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.

Superhost
Home in Pickering
4.77 out of 5 average rating, 105 reviews

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.

Superhost
Condo in Humber Bay Shores
4.79 out of 5 average rating, 104 reviews

Humber Bay Family Friendly condo w Terrace&Parking

Located in Toronto's west end, overlooking the lake with bike paths, kayaking and canoeing, beaches and boating at your doorstep. Classic decor with a large terrace/balcony for entertaining. Steps away from restaurants, bars, and shopping with groceries and LCBO across the street.

Popular amenities for Pickering waterfront rentals

Quick stats about waterfront rentals in Pickering

  • Total rentals

    60 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Durham Region
  5. Pickering
  6. Waterfront rentals