House holiday rentals in Pickering

4.93 out of 5 average rating, 375 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!

The exterior of a two-story home showcases a brick façade with a blue garage door. A welcoming front porch features seating, while a neatly landscaped pathway leads to the entrance. Ample windows allow natural light to brighten the space.

4.87 out of 5 average rating, 208 reviews

Cheerful 4-bedroom home with huge patio

This bright and airy 4 bedroom 3 bathroom home is perfect for a family or a friends getaway. High speed internet and full amenities. Minutes from Deercreek Golf Course, the NEW Thermëa spa, top rated restaurants, supermarkets, and shopping. Easily accessible by highway 401 or 407/412. 45-min drive to downtown Toronto. 10-min drive to Whitby GO Train station. Perfect for families, business trip or a weekend getaway, your stay here is sure to be convenient and effortless. Long-term stays welcome.

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, 119 reviews

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

Welcome! Our 3 bedroom, 2 bath home is centrally located on a low traffic court. Spacious, clean and bright! Featuring a large walk-out family room with high ceilings and a wood-burning fireplace. Completely renovated with wood floors throughout. Large sunny west-facing backyard and 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!

A cozy living space features a modern television stand with a flat-screen TV, accentuated by a bold artwork. A gray couch with yellow cushions invites relaxation, complemented by a light rug atop wooden flooring. Large windows allow natural light to brighten the room.

4.86 out of 5 average rating, 228 reviews

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!

A bright living area features a neutral-toned sofa positioned across from a wooden coffee table adorned with a small vase of colorful flowers. A wall art piece of abstract design adds visual interest. The open layout includes doorways leading to the kitchen and bedrooms.

4.86 out of 5 average rating, 156 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!

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, 140 reviews

4BR |Chef Kitchen| Casino Dagmar Thermea (15km)

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.

4.98 out of 5 average rating, 129 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.

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, 127 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 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.

4.9 out of 5 average rating, 141 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, 163 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

A modern living area features a pair of vibrant blue sofas arranged around a decorative area rug. Large windows allow natural light to brighten the space, complemented by a sleek kitchen with dark cabinetry and stainless steel appliances visible in the background.

4.86 out of 5 average rating, 211 reviews

Luxurious & Modern Guest Suite-Walkout Bsmt Apt.

Luxurious new constriction basement apartment in central Whitby. Gorgeous kitchen, living area, and laundry. Ravine lot with excellent views of forest nearby. One stunning bedroom and one 3pc bath. One Free parking on the premises! Please keep in mind we do have a dog on the property. Please note: The kitchen only has a wine fridge. We do not have a freezer.

A neatly arranged living room features a pair of comfortable gray sofas with accent pillows, complemented by a glass coffee table at the center. Light filters through a large window, illuminating the space, while a decorative area rug adds a cozy touch.

4.92 out of 5 average rating, 285 reviews

Stylish Home near Luxury Spa & GO Station

Perfect for SPA. SKI. OPG. Port Whitby, Marina. Sport Teams. ENTIRE HOME. Pro Foosball. Backyard Trail. Internet, Wifi, Netflix, Spotify, Bar, Pro Bonzini Foosball Table, trail in backyard, walking distance to GO, 3min to Hwy 401. Calm neighborhood with many facilities: restaurants, shopping centers, movie theatre, playdium and more.

Popular amenities for Pickering house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 25 reviews

Home in Etobicoke

newly renovated, close to airport, washer/dryer

4.92 out of 5 average rating, 13 reviews

Home in Etobicoke

Seraya Wellness Retreat

5 out of 5 average rating, 26 reviews

A refreshing outdoor pool is surrounded by a wooden deck, offering ample lounge chairs for relaxation. Lush greenery frames the area, creating a serene atmosphere. The pool's clear turquoise water invites enjoyment, while the natural landscaping enhances the overall privacy of the space.

Home in North York

Award Winning Luxury Home with Heated Pool + Sauna

4.94 out of 5 average rating, 234 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, 167 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

4.9 out of 5 average rating, 99 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Rouge

Ravine Paradise ! heated pool and hot tub!

4.85 out of 5 average rating, 96 reviews

The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.

Home in Uxbridge

The Ridge Roost - Uxbridge Township

4.91 out of 5 average rating, 327 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 – TIFF & FIFA at Your Door

Weekly house rentals

A modern kitchen is featured with sleek cabinetry and a breakfast bar, accompanied by four dark leather chairs. A cozy living area includes a large sectional sofa facing a mounted flat-screen television. Warm lighting enhances the ambiance of the space.

4.94 out of 5 average rating, 36 reviews

Modern Basement Apartment

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.

5 out of 5 average rating, 27 reviews

Serene Urban Retreat/15 min walk from Thermea Spa

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.

4.86 out of 5 average rating, 29 reviews

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

4.93 out of 5 average rating, 41 reviews

3 bedroom bungalow in South Ajax

5 out of 5 average rating, 7 reviews

Cozy 2-bedroom with kitchen

The entrance features a white door framed by large windows, allowing natural light to enter. Decorative planters filled with vibrant flowers flank the steps, leading up to a welcoming mat. The exterior is complemented by dark shutters on either side.

4.95 out of 5 average rating, 73 reviews

Cheery 1941 Historic Home in Ajax

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.

4.91 out of 5 average rating, 47 reviews

Modern cozy living.

A modern kitchen is shown, featuring sleek cabinetry, open shelving, and an island with seating. A dining table is positioned nearby, surrounded by gray chairs. Two pendant lights hang overhead, illuminating the space. Stainless steel appliances are visible, enhancing the contemporary feel.

4.93 out of 5 average rating, 42 reviews

Elegance and Comfort

Private house rentals

4.96 out of 5 average rating, 48 reviews

A welcoming living area is furnished with a comfortable sofa and a coffee table. Natural light enters through the front door, complemented by large windows. A television is positioned on a low cabinet, while a floor lamp adds additional lighting to the space.

Home in West Rouge

Quiet upscale neighbourhood

5 out of 5 average rating, 13 reviews

Beautiful End-unit Townhome with Lakeview Room

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, 52 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.

4.89 out of 5 average rating, 37 reviews

Cozy private backyard garden studio

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.

4.83 out of 5 average rating, 54 reviews

Holiday Hideout Basement Unit

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.

4.99 out of 5 average rating, 70 reviews

Near Toronto - Family Retreat - {Entire Property}

4.92 out of 5 average rating, 12 reviews

An exterior view of a spacious detached house is presented, featuring a double garage and a paved driveway. Snow blankets the ground, and the brick facade complements the light blue sky. The adjacent properties are visible, highlighting a peaceful neighborhood setting.

Home in Oshawa

Lovely & Spacious place to stay

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.