Beachfront holiday rentals in Pickering

Lakefront Cottage + Boathouse & Sunsets

Lakefront summers with spectacular sunsets, private dock, and a relaxed boathouse hangout. Spend your days kayaking, paddleboarding, swimming, and fishing, then wind down with evening fires and sunset views over the lake. The cottage is a cozy, comfortable space for easy family lake days, with room to gather, unplug, and enjoy time together. When you feel like exploring, historic downtown Port Perry is just minutes away, along with local wineries, breweries, live music, and day-trip adventures.

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.

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.

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

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 Breeze Apartment, EV Charging & 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!

Private guest suite in the Beaches

Steps from vibrant Queen Street and just across the street from Kew Gardens - a beautiful park that takes you to the beach in less than 5 minutes. You will have a private entrance to a basement suite that's entirely yours! 🏖️ Attractions nearby: waterfront, boardwalk, hidden ravine, parks, Queen Street with shops, cafes, and restaurants, outdoor activities, easy streetcar to downtown Toronto. About a 40 minute Uber to Pearson Airport, and 15-20 minute Uber to downtown Toronto.

Lakefront Stylish 2-Bedroom Condo with Pool

Experience the blend of comfort and character in this beautifully styled condo featuring a spacious open-concept layout, with 10 ft ceilings and an inviting vintage decor. Step out onto the large private terrace to take in breathtaking panoramic views of lake, the iconic Toronto skyline, and the lush greenery of Humber Bay Park. Nestled in a prime location just steps from scenic bike paths, water activities, restaurants, grocery stores, public transportation, and the marina!

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Waterfront community ideally for long stays

Furnished 4 bedroom, 2.5 bathroom Executive townhouse located in upscale neighborhood in Bowmanville waterfront community. Close the Hwy 401 and all shopping center. Bowmanville Hospital and the Go bus service. Easy access to nice restaurants and many more amenities. It is bright, spacious, with many beautiful features. All inclusive (parking, tv and internet included) The basement will be rented separately.