Waterfront vacation rentals in Pickering

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Pickering

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

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Guest favourite

Home in Ajax

4.93 out of 5 average rating, 15 reviews

Private Suite - Ajax by the Lake

Private guest suite, newly renovated in lower level of our house with separate entrance. Short distance to the Lake and parks, 5 min drive to Ajax GO and Highway 401. Space is family friendly in a quiet neighborhood. 30 min drive to Downtown Toronto, and 40 min drive to Pearson Airport. Close to casino. Space Fully equipped kitchen, double bed, queen sofa-bed, washer/dryer, microwave, kettle, toaster, Nespresso, Chromecast and WIFI. No - Drugs, pets, parties. Property monitored by cc cameras.

Dec. 18 – 25

$107 CAD per night

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 533 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.

Feb. 16 – 23

$513 CAD per night

Superhost

Cottage in Bowmanville

4.87 out of 5 average rating, 118 reviews

Super Cute & Modern 3 Bedroom Beach Bungalow

Transport Yourself To This Modern, Open Concept, 3 Bedroom Beach House & You Will Feel Like You Have Left The Country! Only An Hr From Toronto. Take In The Stunning Views Of Lake Ontario & Relax Over The Lapping Sounds Of The Waves. Enjoy Direct Access to The PRIVATE Beachfront & The Outdoor Space (Drum fire pit, Patio Set, BBQ)-It's The Perfect Urban Getaway. You Get The Entire House & Lots Of Parking Available. ABSOLUTELY NO PARTIES PERMITTED. Pls read all rules before booking. No pets.

Aug. 12 – 19

$586 CAD per night

Superhost

Home in Bowmanville

4.89 out of 5 average rating, 105 reviews

Luxury Waterfront Bowmanville getaway home!

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

Apr. 27 – May 4

$408 CAD per night

Guest favourite

Apartment in Richmond Hill

4.95 out of 5 average rating, 298 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.

Dec. 16 – 23

$154 CAD per night

Superhost

Cottage in Bowmanville

4.86 out of 5 average rating, 103 reviews

Waterfront Beach House Oasis - All Season Hot Tub!

Welcome to the one of a kind beach house - Paradise just outside of the City! Our waterfront 4 bedroom property features unobstructed lake views, a view of an infinite horizon featuring breathtaking sunsets, kayaks, a fire pit, BBQ, and an all-season hot tub. Whether it’s staying in and enjoying a movie, relaxing on our private beach, or exploring the nearby Darlington conservation areas, our home will provide you with everything you need for the perfect urban getaway!

Sep. 3 – 10

$813 CAD per night

Guest favourite

Condo in Toronto

4.95 out of 5 average rating, 170 reviews

Upscale Luxurious Condo Free Parking

IN THE HEART OF IT ALL....CONDO IN THE CLOUDS The Space Come stay and enjoy the awesome VIEW from my private condo. Situated in the heart of it all....SCOTIA BANK CENTRE, ROGERS CENTRE, RIPLEY'S AQUARIUM, METRO TORONTO CONVENTION CENTRE, THE WATER FRONT, THE ENTERTAINMENT DISTRICT AND THE HOCKEY HALL OF FAME. Longo's Grocery Store, Starbucks, Bank(TD), Real Sports Bar, Eleven Restaurant, Sports Store and the Path System all located at the main floor of the condo.

Mar. 25 – Apr. 1

$317 CAD per night

Superhost

Guest suite in Pickering

4.8 out of 5 average rating, 144 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.

Oct. 1 – 8

$168 CAD per night

Guest favourite

Cottage in Richmond Hill, Canada

4.94 out of 5 average rating, 127 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Sep. 18 – 25

$446 CAD per night

Guest favourite

Dome in East Gwillimbury, Canada

4.92 out of 5 average rating, 129 reviews

Deerleap Glamping Dome

Looking for a peaceful escape from the city? Our glamping dome offers just that, situated on 10 acres of picturesque land with trail, streams, and a stunning pond view. Perfect for a romantic retreat or a weekend getaway with the family, our dome is equipped with everything you need, from upscale sanitary to fast Wifi. Relax and enjoy the starry sky from the comfort of your bed, gather around the bonfire for s'mores , or explore nearby Lake Simcoe.

Nov. 15 – 20

$292 CAD per night

Guest favourite

Condo in Toronto

4.96 out of 5 average rating, 248 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.

Nov. 1 – 8

$312 CAD per night

Guest favourite

Condo in Toronto

4.89 out of 5 average rating, 125 reviews

Cozy & Spacious DT Condo - entire apartment

You will have the ENTIRE Unit to yourself and will not share with others. All rooms are yours! Located in the heart of Downtown. This Tridel 5-Star Boutique Style Condo is the perfect place where you can have easy access to 2 supermarkets, LCBO, great restaurants, shopping, entertainment and nightlife! Steps to Entertainment/Financial Districts, Rogers Center, Waterfront & CN Tower!!!

Dec. 7 – 14

$263 CAD per night