House holiday rentals in Pickering

4.93 out of 5 average rating, 396 reviews

“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!

Superhost

A modern kitchen area is presented with sleek white cabinetry and black appliances, complemented by a textured backsplash. A dining table with two black chairs sits invitingly, while greenery is introduced by a potted plant in the corner, enhancing the clean and contemporary design.

Guest suite in Scarborough

4.94 out of 5 average rating, 125 reviews

Gorgeous Modern 2BR Suite | Swim Pool | Fire Table

Welcome to our brand new, luxury modern suite located in a quiet, family-friendly neighbourhood. Mins to HWY401/DVP, TTC. Featuring: ✓ Luxury Finishes Throughout ✓ Heated Swimming Pool (seasonal April - Oct) ✓ Dedicated Workspace ✓ Washer/Dryer ✓ High-Speed WIFI ✓ Smart TV with Netflix, Prime & sound system ✓ Keyless Entry (24/7 Self Check-In) ✓ Outdoor BBQ, seating and fire table This upscale oasis is truly the perfect space for business travellers, young professionals & couples alike!

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

4.85 out of 5 average rating, 121 reviews

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!

4.86 out of 5 average rating, 162 reviews

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!

4.99 out of 5 average rating, 243 reviews

Home in Corktown

Stylish 1870s Home near Distillery District & Old Toronto

Named a Top 1% by Airbnb, former Plus listing & top 10 Toronto stay by BlogTO, this beautifully restored 1870s rowhouse blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown steps from St. Lawrence Market, the Distillery District, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

The living room features a large sectional sofa and a coffee table with a decorative plant. A modern gas fireplace is situated beneath a wall-mounted television displaying a streaming service. Sunlight fills the space through multiple windows, creating a bright and cozy atmosphere.

4.99 out of 5 average rating, 149 reviews

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)

A cozy bedroom features a spacious bed with elegant bedding, flanked by two nightstands. A dresser is positioned against the wall, and natural light filters through a window, illuminating the soft grey walls and light-colored flooring.

4.99 out of 5 average rating, 155 reviews

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.

4.89 out of 5 average rating, 117 reviews

A spacious living area features a large sectional sofa facing a modern fireplace. Light wood flooring complements the warm color palette. An open floor plan is highlighted, with a view of the kitchen in the background, which includes sleek cabinetry and a large island.

Home in Oshawa

Modern 4BR Home in North Oshawa

Welcome to your modern 4BR, 3.5BA retreat in North Oshawa near Harmony & Collins. Perfect for families or professionals, this spacious home offers comfort and style with a bright open layout. Just 15 mins to malls, groceries & fine dining, with quick access to Hwy 401/407. Explore Lakeview Park, Parkwood Estate & Tribute Communities Centre nearby. Exterior security cameras ensure peace of mind. Early check-in/late check-out available!

The living area features a spacious couch and two cozy blue accent chairs, positioned around a round coffee table. A large flat-screen TV is mounted on the wall, while a modern mirror reflects the open concept layout, enhancing the light from the recessed lighting.

5 out of 5 average rating, 129 reviews

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.

A spacious living area features a large sectional sofa paired with a modern armchair. Natural light streams through the expansive windows, highlighting a round coffee table and a light-toned area rug underneath. A potted plant adds a touch of greenery to the serene space.

4.88 out of 5 average rating, 133 reviews

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!

A spacious entertainment area features a green felt pool table at the center, surrounded by a plush area rug. Dark leather seating is positioned nearby, alongside a modern dining table with black chairs. Soft lighting enhances the neutral-toned walls and flooring.

4.89 out of 5 average rating, 148 reviews

Beautiful bright basement aptmnt

Property is located walking distance from Kingston and westney, is newly renovated welcoming and has everything you need, private side entrance, a large soaking tub in the washroom with an LED mirror perfect for getting ready for a night out, The basement even has a private washer and dryer so you can get your laundry done whenever you need to as well, a large walk in closet and a lot of space!!

A modern living space is displayed, featuring a wall-mounted television above a sleek dark cabinet. To the right, a laundry area is visible with stacked washer and dryer units. Light hardwood flooring runs throughout the space, contributing to a clean and contemporary look.

4.94 out of 5 average rating, 176 reviews

Luxurious, modern basement unit

Kick back and relax in this calm, stylish space. Prime location near bus stop, shops, restaurants there is something for everyone. Whether you are here for work or pleasure this is your best place. Your home away home. Nice and modern new basement apartment with fast and reliable fibe internet , smart TV with Netflix, Amazon prime and Disney plus , dedicated work space and free parking

Popular amenities for Pickering house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 51 reviews

A heated swimming pool is nestled in a lush backyard, surrounded by vibrant greenery and mature trees. The pool features a diving board and is set against a backdrop of colorful plants, creating a serene outdoor retreat.

Home in Mississauga

Luxury House with a Bright Sunroom & a heated pool

An aerial view showcases a spacious retreat surrounded by lush greenery. A sparkling pool is featured alongside a shaded seating area and a gazebo, enhancing the outdoor living experience. The property is framed by trees, providing a sense of privacy and tranquility.

4.92 out of 5 average rating, 76 reviews

Beautiful Cottage in Ajax

4.94 out of 5 average rating, 235 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

4.99 out of 5 average rating, 176 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR Oasis: Year Round Heated Pool & Hot Tub

Home in McLaughlin

4.81 out of 5 average rating, 54 reviews

Private Home + PS4 + Foosball: 5 Bedrooms, 3 Baths

4.91 out of 5 average rating, 330 reviews

An open-concept living area features hardwood floors and exposed brick walls. A spacious bed is complemented by elegant chandeliers, while a white futon is situated nearby. Decorative artwork adorns the walls, and a light-filled kitchen area is visible in the background.

Home in West Queen West

Chic King West Studio – FIFA at Your Door

4.9 out of 5 average rating, 20 reviews

A tranquil pool area is framed by a flagstone patio, featuring a covered BBQ station and a poolside bar. Lounge chairs are arranged around the pool, with a shaded space visible nearby. Lush greenery and a clear sky complement the inviting outdoor setting.

Home in Mississauga

Oakwood Haven

4.89 out of 5 average rating, 95 reviews

A bright and airy living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central rug, while a wall-mounted television provides entertainment. The entrance is visible with a stylish door and greenery outside.

Home in Don Mills

Casa Meya – Toronto Poolhouse Villa

Weekly house rentals

Superhost

Home in Whitby

5 out of 5 average rating, 3 reviews

Beautiful townhouse -19

Superhost

A modern living area features leather seating arranged around a glass coffee table. A sleek, wall-mounted fireplace adds warmth. In the background, an open-concept kitchen is visible, equipped with contemporary appliances and a dining area with black chairs. Natural light enters through the windows.

4.78 out of 5 average rating, 36 reviews

Blue Dream: Modern Gem 6B/3.5B,Office,5G,Parking!

4.93 out of 5 average rating, 42 reviews

3 bedroom bungalow in South Ajax

4.87 out of 5 average rating, 89 reviews

Luxury & Stylish 3BD | Chefs Kitchen & Cozy

The modern kitchen features sleek cabinets with a light finish, stainless steel appliances, and ample countertop space. Under-cabinet lighting highlights the cooking area. A wood-look floor complements the overall design, creating a clean and functional space.

4.92 out of 5 average rating, 53 reviews

Modern cozy living.

The living area is furnished with a dark velvet sectional sofa and a matching armchair, arranged around a glass coffee table. A decorative mirror and subtle lighting enhance the space. A view into the kitchen and hallway is visible through an open layout.

4.96 out of 5 average rating, 25 reviews

Cozy Detached 3BR Home | Full Gym | Prime Location

4.96 out of 5 average rating, 46 reviews

The front exterior of a spacious two-story home is shown, emphasizing a manicured lawn and a paved driveway leading to a double garage. A covered porch features two wooden chairs, while large windows invite natural light.

Home in Scarborough

Rouge Hill Retreat srt-2310-hbprvw-rnwl-2509

4.93 out of 5 average rating, 40 reviews

The Taunton House

Private house rentals

5 out of 5 average rating, 29 reviews

A spacious lounge area features a large sectional sofa adorned with patterned throw pillows. A light-colored coffee table sits on a decorative rug, with artwork displayed on the wall. Soft lighting enhances the cozy atmosphere of this stylish retreat.

Home in Whitby

Serene Urban Retreat/15 min walk from Thermea Spa

5 out of 5 average rating, 11 reviews

Large house 3 bed 2 bath 2 parkings

4.99 out of 5 average rating, 75 reviews

An open-concept living area features a large wall-mounted television against a marble design backdrop. A round coffee table is placed on a patterned area rug, with modern furnishings surrounding it. Soft lighting is provided by ceiling spots and highlighted elements on display.

Home in Oshawa

Ultra Luxury Suite in Oshawa

A well-lit game room features a classic pool table with a green felt surface and wooden frame. Above the table, three green lamps provide ample illumination. In the background, a sleek bar counter and seating area are visible, creating an inviting entertainment space.

5 out of 5 average rating, 58 reviews

Family Friendly Apartment with Private Entrance

A comfortable living area is showcased with a light blue sofa, complemented by decorative pillows and a throw blanket. Two small wooden tables are positioned in front of the sofa on a textured area rug. A room divider holds decorative items, creating separation from the sleeping area. Natural light floods in through large sliding doors adorned with light curtains.

4.9 out of 5 average rating, 41 reviews

Cozy private backyard garden studio

4.84 out of 5 average rating, 55 reviews

A spacious living area features a light-colored sofa adorned with a decorative yellow pillow. A glass-top coffee table displays neutral-colored items, while a plant adds a touch of greenery. The open layout leads to a modern kitchen and dining area, enhancing the inviting atmosphere.

Home in Dunbarton

Holiday Hideout Basement Unit

The exterior of the house is depicted, showcasing its beige stone facade and large windows. The entrance is highlighted by a covered porch with decorative columns. A well-kept lawn and paved pathway lead to the front steps, with a glimpse of neighboring homes in the background.

4.89 out of 5 average rating, 57 reviews

Spacious 5BR Home for Families/Business Travelers

A spacious outdoor deck overlooks a green backyard, featuring a large tree and colorful play equipment. A dining set with six chairs is positioned on the deck, inviting casual gatherings. The yard is enclosed with a privacy fence, providing a tranquil outdoor space.