Beachfront vacation rentals in Pickering

Rainbow House

Make memories in this unique, family-friendly space. Rainbow house includes a variety of outdoor and indoor activities. We provide water equipments in the summer such as boats, kayaks, water bicycles, floating carpets, and more. We also have indoor activities providing you with 8 ball tables, mini soccer game table, archery set for kids, table top hockey table, card games, dice games, and Mahjiong tables as well. Please only stay in this area of the cottage, PLEASE DO NOT TRESPASS to other people's property.

Private Beach, Hot Tub, Axe-Throwing & Chef's Kitc

The ONLY rental in the area with a huge, 100% sandy PRIVATE BEACH! You can stop looking now. Because our paradise is now YOUR paradise. Once owned by one of Canada's most revered artists, this custom home was designed & built by renowned architect D. Veenstra. Along with the sandy beach you get the hot tub (100% hidden from view in summer), kayaks, big yard, deck w/ table for up to 8, Napoleon grill, and firepit. Only 5 min to Hwy 401; 28 to the edge of Toronto; 1h to downtown & YYZ airport.

Cottage at Lake Simcoe

Escape to this charming bungalow at Lake Simcoe's south end, where you can relax on the covered deck with built-in BBQ and bar sink, garden shed, and ambient lighting. With 4 spacious bedrooms, 2 master ensuites, and a large family room, there's plenty of room for socializing. Enjoy fishing, swimming, and boating just steps away, and visit nearby Willow Beach (15 min drive), Orchard Beach Golf and Country Club, and Beach Lakefront Bar and Grill (8 min drive). Private beach(Pine Beach about 1km).

Sunrise Villa on the Lake

Create cherished memories at this enchanting and spacious home nestled on the shimmering waterfront of Lake Simcoe. This spacious house, newly renovated and complete with forced air heating, centre air conditioning. hot tub Jacuzzi, entertaining room with pool & Ping-Pong table, air hockey table &TV, Exotic Bar&bonfire in back yard. You can enjoy 30 feet private dock to parking boats, swimming on the lake, playing 2 Kayaks (10 feet) & a 14 feet flat board, free of charge. Ice fishing in winter.

Luxury & Stylish 3BD | Chefs Kitchen & Cozy

Discover the charm of our inviting 3-bedroom house in the heart of Pickering's family friendly neighbourhood, West Shore. Featuring a newly renovated luxurious chef's kitchen, comfortable living space, and a tranquil layout, our home offers the perfect blend of relaxation and convenience. With Frenchman's Bay just minutes away, you'll have easy access to the best of the beautiful lake. Convenient Location - Minutes to Go Station, Pickering Town Centre and HWY 401! 25 Min. to UNION STN Via GO

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.

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

Stunning 2 bedroom & 2 bath condo in the heart of downtown Toronto! Breathtaking views of the CN Tower, Lake, and southwest sunset. Steps away from the CN Tower, Scotiabank Arena, Rogers Centre, Union Station (airport express train direct), Convention Centre, Waterfront, and more. FREE PARKING for one vehicle. Luxurious amenities: rooftop pool, indoor pool, hot tubs, sauna, gym, theater room, party rooms. Grocery, Starbucks, restaurants, banks, bars inside the building on the ground floor.

Top guest favorite

Guest favorite

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.

Top guest favorite

Guest favorite

Lakefront | Hot Tub, Private Dock & Sandy Beach

Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.

Lake Breeze 2Bed Basement Apart, EV & Free Parking

Welcome to Lake Breeze, right in the heart of the city with breathtaking views of Lake Ontario just steps from your door! This brand new, beautifully lit built 2 bedrooms basement apartment offers a rare blend of cottage charm and modern comfort. Wake up to serene lake views and enjoy the peaceful atmosphere, all while staying in town!!! Whether you’re visiting for a weekend escape or a longer stay, this space is perfect for those who love nature, comfort, and convenience all in one place.

“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!

Grand Waterfront Retreat – Under 1hr from Toronto

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!