
House holiday rentals in Pickering
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Top-rated house rentals in Pickering
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“Elysium” Where happiness is real!
Stay connected with our fast Bell Fibe Wi-Fi, free parking and unwind with over 1000 streaming channels on our TV, including Netflix and Prime. Whether you're here to catch the game or watch an exciting fight you’ll have everything you need for a great time Our location is the perfect base for discovering all that Pickering has to offer. You’ll be just a short drive away from fantastic restaurants, lively bars, shopping spots, and even casinos—everything you need for a fun and convenient stay!

Family Friendly Basement with Separate Entrance!
Open concept basement apartment (No walls separating rooms) 1 Queen bed and a Futon folds out into a Double bed . Accommodates Family of 4, NOT 4 Adults (2Adults/2children) . Separate entrance/ONE prkg spot. Located in a quiet neighbourhood in Pickering. Family friendly, NO parties/gatherings. Close to public Transit. 5 minutes drive from U Of T (Scarborough) Close to Toronto Zoo, PanAm Center, Go Stn and Hwy- 30 mins to Downtown Toronto. PLEASE read ALL house rules prior to booking.

Luxury 4BR Retreat ~ Spacious Home ~ Pickering
Welcome to our Newly Furnished and Professionally Cleaned home in Pickering ✓ 4 Bedroom, 3.5 washroom ✓ Fully equipped kitchen for preparing meals ✓ Cozy Family Rooms ✓ Brand New High-quality Linens, Comfy Beds ✓ 85" Smart TV, High-speed WiFi ✓ In suite washer & dryer ✓ Backyard with green scenic view ✓ Free parking! ✓ Safe neighbourhood ✓ Enjoy easy access to the Toronto Zoo, Canada’s largest, located just 10 minutes away. Book your stay with confidence and make unforgettable memories!

Quiet Vaughan Retreat near Wonderland & Hwy 400
Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Spacious, Modern & Cozy Retreat
Welcome to our spacious, cozy, and family-friendly Airbnb, perfectly designed to accommodate both large and small families. Centrally located, you'll be just minutes away from shopping centers, grocery stores, and major highways, making it easy to explore the city. Enjoy a comfortable stay with all the amenities you need, including a fully equipped kitchen, a relaxing living area, and a backyard for outdoor fun. Ideal for a memorable family getaway in a convenient and vibrant neighborhood!

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
Contemporary 3 bed, 2 bath home w/ a European-feel. Centrally located on a low traffic court. Spacious, clean & bright! Featuring a large walk-out family room, high ceilings and wood-burning fireplace. Renovated w/ wood floors throughout. Large sunny west-facing backyard + 6 car-park on the driveway. Enjoy many unique amenities like our chromo-therapy steam room & outdoor Brazilian hammock. Walking distance to strip plaza, restaurants & parks. A comfortable home away from home!

Walk to Lake | 2BR Family Suite | Near Toronto
✨ Prime Location – 3 mins to HWY 401, Pickering GO & Town Centre 🌊 In West Shore — walk to the beach, lighthouse & Lake Ontario! Perfect for sunrise & family strolls. 🛌 Fully private walk-up basement suite — no shared spaces, clean & comfy • 2 comfortable bedrooms + spacious living room 🚗 Free parking for 2 vehicles 🍳 Full kitchen for easy meals 👨👩👦 Ideal for families & travelers exploring Toronto 🌟 Enjoy complete privacy, comfort & beachside vibes in Pickering!

Toronto [45 mins] Sleep 8| Free Parking | Backyard
Why you will love your stay here: - ***ENTIRE HOME*** No one will be on the property but those on the booking. This is a DETACHED house. No connecting houses. - Open concept on the main floor so you can connect and create memories - Dedicated work from home spaces . Cat 6 ports -The 2nd floor has 4 different rooms where you can unwind and take a much deserved break - 10ft ceilings on a corner lot with lots of sunlight - Central Hub to Toronto (45 min drive)

Luxury 2BR Townhouse• Chic Design & Top Amenities
Step into pristine luxury — a bright, clean, meticulously detailed townhouse filled with glass and crystal touches. Open, airy spaces invite you to relax in style, where every detail has been thoughtfully designed for comfort and elegance. Enjoy ultimate relaxation with our top tier home entertainment setup, complete with smart TV and full streaming access for movie nights or binge-watching. Immaculate, modern, and effortlessly inviting — your perfect escape awaits.

Private Sauna Suite Retreat
1 Bedroom • 1.5 Bathrooms • Private Entire Unit Newly renovated and quiet, just minutes from Hwy 401 and local restaurants. Highlights • Private self check-in • Driveway parking for 1 car • Private sauna • 55 Inch TV with Netflix Amenities Fresh towels, linens, tooth brushes & pastes, hairdryer, home essentials, shower essentials, and extra pillows/towels on request. Spotless home, quick replies, and your comfort guaranteed - book with confidence.

Ultra-Modern Luxury Retreat! Close to Thermea SPA.
COZY and INVITING, this modern suite is in a quiet, family-friendly Ajax neighborhood. Just 10 minutes to Thermea Spa and Ajax GO Station, and a short walk to parks, shops, and groceries. Newly built with deluxe finishes, the 1,000 sq. ft. space includes in-floor heating, an electric fireplace, a spacious sofa, and smart TV with Netflix/Prime. Downtown Toronto is 35–45 mins by car, and Pearson Airport or Mississauga in about 55 mins.

Serene Stays - Pickering (5Beds, 2.5Baths, 4Park)
Welcome to Serene Stays - Pickering, where you'll find comfort, style, and convenience all come together! This is a newly built, spacious 4 bedroom, 2 storey home where you can completely relax with access to the entire home - boasting 4 bedrooms, 2.5 bathrooms, living room, dining room, full kitchen, private outdoor patio, and laundry room. This home has 4 parking spaces and is perfect for large families or groups!
Popular amenities for Pickering house rentals
House rentals with a pool

Walk-out Luxury basement with Gym & Theatre

Beautiful Cottage in Ajax

Private river access with pool, canoes, kayak

Home away from home with a hot tub and pool

Vacation Spa Retreat! Sauna, pool, gym

Chic King West Studio – FIFA at Your Door

Casa Meya – Toronto Poolhouse Villa

The Serenity Home Pool/Yoga/Game Room by the Lake
Weekly house rentals

Beautiful townhouse -19

Large house 3 bed 2 bath 2 parkings

Family Friendly Apartment with Private Entrance

Maple Nest Pickering for your stay

Spacious 5BR Home for Families/Business Travelers

New Cozy Walkout Basement Studio Getaway

Luxury & Stylish 3BD | Chefs Kitchen & Cozy

Cheery 1941 Historic Home in Ajax
Private house rentals

Quiet upscale neighbourhood

Serene Urban Retreat/15 min walk from Thermea Spa

1 bedroom studio private basement in Pickering

Beautiful 3bedroom home away from home in Ajax

3 bedroom bungalow in South Ajax

The Reach

Entire 2 Storey Home 1Bdrm Private

Elegance and Comfort
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $109 NZD | $112 NZD | $112 NZD | $118 NZD | $123 NZD | $124 NZD | $126 NZD | $131 NZD | $124 NZD | $121 NZD | $118 NZD | $118 NZD |
| 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 house rentals in Pickering

Total holiday rentals
Explore 1,080 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 21,060 verified reviews to help you choose

Family-friendly holiday rentals
480 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 170 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
640 properties have a dedicated workspace

Wi-Fi availability
1,030 of Pickering holiday rentals include Wi-Fi 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
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- Smoking-friendly rentals Pickering
- Condo rentals Pickering
- Private suite rentals Pickering
- Apartment rentals Pickering
- Rentals with lake access Pickering
- Pet-friendly rentals Pickering
- Rentals with an EV charger Pickering
- Rentals with breakfast Pickering
- Rentals with pools Pickering
- Waterfront rentals Pickering
- Beachfront rentals Pickering
- Cottage rentals Pickering
- Rentals with a fire pit Pickering
- Family-friendly rentals Pickering
- Rentals with outdoor seating Pickering
- Rentals with a hot tub Pickering
- Rentals with beach access Pickering
- Fitness-friendly rentals Pickering
- Rentals with a patio Pickering
- Guesthouse rentals Pickering
- Townhouse rentals Pickering
- Rentals with a fireplace Pickering
- Rentals with a washing machine and dryer Pickering
- House rentals Durham
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Downsview Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- York University
- Scarborough Town Center




