
House holiday rentals in Pickering
Find and book unique houses on Airbnb
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 $18 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
Top-rated house rentals in Pickering
Guests agree: These houses are highly rated for location, cleanliness and more.

“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!

Brand New Private Luxury Suite Open Consept living
Sun filled Private Suite, cozy & modern. Entire space with separate entrance. Peaceful Ravine, walking path & Sunrise. Minutes to the 401 & Ajax GO Station. 18 min to Toronto Pan Am Sports Centre. Drive or GO to downtown Toronto. Walking distance to a wide variety of restaurants, major shopping plazas, Walmart, Costco, RCSS, Iqbal foods, Ajax Downs & Casino. Life Time Athletic, Ajax convention Centre. Minutes to Lake Ontario & Pickering Casino. 12 min to Dagmar Ski Resort & Whitby Thermëa spa.

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.

Private Look-out Basement 2Bed 1 Bath Full Kitchen
Hello Airbnb Renters! 1300SQ.FT 9FT CEILING LOOKOUT 2 BEDROOM 1 FULL BATH FULL CUSTOM KITCHEN LIVING DINNING ROOM WALK-IN CLOSET INCLUDED: 2 BEDS, PILLOWS & COMFORTER STOVE/FRIDGE/MICROWAVE/PORTABLE HEATER LIMITED KITCHEN ACCESSORIES-PLEASE SEE PHOTOS SOFA TV COFFEE MAKER COMPLIMENTARY INSTANT COFFEE PWDER/MILK/SUGAR. 2 BATH TOWELS & HAND TOWELS MUST BRING UR BATHROOM ACCESSORIES & EXTRA TOWELS RESTRICTIONS: NO SMOKING/VAPING INSIDE OR OUTSIDE OR WITHIN THE COMMUNITY AREA NO PETS

Top 1% Clean | 3BR 2BA Suite | 10m to TPASC & Zoo
Enjoy a clean, spacious, and highly rated 3-bedroom suite in a quiet Toronto neighbourhood—perfect for families, wedding guests, and small groups. ⚽ Convenient access to Toronto World Cup events and stadium area via GO Train 🛏 Comfortably sleeps up to 6 guests, 🚗Free parking for up to 4 vehicles 🔑 Easy self-check-in with smart lock ~~This bright garden-level suite features a private entrance, large windows, and abundant natural light. Access is via a short flight of stairs.~~

Moons & Noons -Separate Unit for your Comfort
Welcome to our charming retreat in Ajax! You'll be greeted by living space adorned with carefully curated decor. The sofa beckons you to unwind, while the large windows' scenic views allow natural light to fill the room. Just take a stair down to the Basement, to be greeted by an elegant kitchenette. Enjoy a drink on the sofa while watching shows on 55' QLED. Step into a world of relaxation in our stunning bathroom designed to calm your stress. Your unforgettable stay awaits U!

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!

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)

Walk to Lake | 2BR Family Suite | Near Toronto
✨Prime Location—3 mins to HWY 401 & GO Station 🌊West Shore—walk to beach & Lake Ontario 🏡Fully private walk-up basement suite with its own exclusive entrance, full kitchen & bath. NO SHARED INDOOR SPACES! (Note: Host's family & another group of quiet tenants live in separate units upstairs with their own access. Zero physical contact.) 🛏️2 Comfy bedrooms + spacious living room 🚗Free parking for 2 vehicles 👥Ideal for families & travellers

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 • 65 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

Beautiful Cottage in Ajax

Private river access with pool, canoes, kayak

Home away from home with a hot tub and pool

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

Modern Toronto Home w/ Pool, Hot Tub, Sauna | 4BR

Ravine Paradise ! heated pool and hot tub!

Comfortable &Stylish 4BD Stay Near Toronto Airport

private backyard SPA oasis in Toronto
Weekly house rentals

Home away home

Large house 3 bed 2 bath 2 parkings

Roro's Comfy Basement

Cedar Nest - 5 Beds, 3.5 Bath, 2 Park, Backyard

Just Like Home- Brand New 4 Bedroom Home

Luxury 4BR Retreat ~ Spacious Home ~ Pickering

1 bedroom studio private basement in Pickering

Luxury & Stylish 3BD | Chefs Kitchen & Cozy
Private house rentals

Spacious 3-Bedroom + Den Townhouse with Parking.

Brand New 4 Bdr House in Pickering

Cozy 2-bedroom with kitchen

Near Toronto l Family | Backyard Oasis | 4 Bdrm

Cheery 1941 Historic Home in Ajax

Luxurious Home Away From Home

3-Bed 3-Bath CozyVac House in Ajax,Greater Toronto

Detached Oasis 4-Bedroom, Pickering
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $126 NZD | $124 NZD | $128 NZD | $122 NZD | $128 NZD | $129 NZD | $131 NZD | $136 NZD | $129 NZD | $126 NZD | $122 NZD | $122 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 |
Destinations to explore
- Montreal Holiday rentals
- Pittsburgh Holiday rentals
- Cleveland Holiday rentals
- Detroit Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- Mont-Tremblant Holiday rentals
- Buffalo Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Niagara Falls Holiday rentals
- Rochester Holiday rentals
- Rentals with beach access Pickering
- Townhouse rentals Pickering
- Rentals with a fire pit Pickering
- Rentals with breakfast Pickering
- Rentals with a washing machine and dryer Pickering
- Condo rentals Pickering
- Rentals with a patio Pickering
- Waterfront rentals Pickering
- Private suite rentals Pickering
- Pet-friendly rentals Pickering
- Rentals with outdoor seating Pickering
- Apartment rentals Pickering
- Rentals with an EV charger Pickering
- Rentals with a hot tub Pickering
- Family-friendly rentals Pickering
- Rentals with pools Pickering
- Guesthouse rentals Pickering
- Smoking-friendly rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with a fireplace Pickering
- Beachfront rentals Pickering
- Cottage rentals Pickering
- Rentals with lake access Pickering
- House rentals Durham
- House rentals Ontario
- House rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- Downsview Park
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Toronto Zoo
- Exhibition Place
- Scarborough Town Center
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Enercare Centre
- Yorkdale Shopping Centre
- York University
- Coca Cola Coliseum
- Sheppard–Yonge Station
- Dufferin Grove Park





