Vacation rentals in Pickering

A rooftop terrace features an expansive seating area with grey wicker furniture arranged around a central table. Lush greenery outlines the space, providing a vista of the city skyline under a partly cloudy sky.

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

4.99 out of 5 average rating, 143 reviews

A spacious bedroom features large windows that provide a clear view of the surrounding trees and outdoor park area. A shelf with books and decorative items displays alongside a small table adorned with seasonal decorations, creating a calm and inviting environment.

Home in The Beaches

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

4.78 out of 5 average rating, 9 reviews

Guest suite in Uxbridge

Hilltop Getaway|Scenic Views |Back to ForestTrails

Escape to this stunning hilltop 2-bedroom Airbnb, nestled on 22 acres of beautiful woodland just 2 minutes from Lake Ridge Ski Resort.Enjoy breathtaking panoramic views of the mountains from your private retreat, perfect for those seeking both relaxation and adventure This cozy unit is ideal for hikers, with direct access to Glen Major Forest and scenic trails right at your doorstep There is no living room, you will have 2 bed rms, 1 washroom and a kitchen This unit is a portion of main cottage

4.87 out of 5 average rating, 71 reviews

The exterior view of the lakeside retreat displays a modern blue structure with large glass doors leading to the living area. A spacious wooden patio features a dining table surrounded by chairs, while a hammock is positioned for relaxation. Lush greenery and the lake can be seen in the background.

Home in Bowmanville

*Lakeside Retreat: Viva La Vida*

Modern Aesthetic meets Lakeside Luxury with Close Proximity to a lot of Activities! - 3 Beds/1.5 Bath to sleep 8 - 2 Queen size beds & 4 single bunk bed spaces - 60'' Flat-screen TV ( Amazon Prime, Netflix, Smart TV) - Fully equipped kitchen with modern appliances - Coffee Machine - Cozy living room with ample seating - Outdoor furniture for lakeside relaxation - In-suite Washing machine & Dryer - 1000 MBPS Wi-Fi - Washer and dryer for your convenience - 3 car parking space - Large patio

Home in Churchill Meadows

The exterior view features a modern two-story house with a stone facade and a welcoming front porch. A neatly landscaped yard with shrubs and a tree provides a touch of greenery. The double garage doors are prominently displayed, complementing the home's elegant design.

4.9 out of 5 average rating, 41 reviews

Holiday retreat in Toronto

Make memories at this one-of-a-kind, family-friendly haven. With 5 bedrooms and 3.5 baths, it offers ample space. Only 2 kms from RIDGEWAY PLAZA and Meadowvale Town Centre. On a quiet street yet only 2 kms from the largest restaurant cluster in entire Toronto. An experience not comparable to anything in entire Canada. The fully equipped kitchen and the high-end mattresses ensure restful sleep. The tasteful decor adds a special touch. House is professionally cleaned between bookings.

5 out of 5 average rating, 20 reviews

Home in Courtice

Home away from Home

Private, relaxing, bright one bedroom , 900 sq ft walk-out basement apartment. This home is nestled on a quiet court which backs on to a forested ravine. Enjoy relaxing on the backyard patio with your morning coffee or evening wine and enjoy the tranquil nature setting. The home features a beautiful kitchen, large breakfast island, open concept living room with work space, cozy gas fireplace, large bedroom with walk-in closet and a beautiful 3pc bathroom with frameless glass shower.

A modern living space features large windows with city views, complemented by a stylish dining area. A marble coffee table sits centrally, while a sleek TV unit and vibrant yellow dining chairs enhance the contemporary design. Unique wall patterns add visual interest.

4.93 out of 5 average rating, 15 reviews

Beautiful 1BR Condo Coveted Yorkville!

Welcome to our stylish and luxurious Yorkville condo! Immerse yourself in the heart of Toronto's most upscale neighbourhood, surrounded by top-rated shopping, renowned restaurants, and cultural attractions. This chic retreat offers modern amenities, elegant design and a prime location for an unforgettable stay in a newly-constructed building. ➜ Approx. 500ft² / 56m² of space ➜ Highspeed WIFI ➜ In-unit washer & dryer ➜ Fully equipped kitchen ➜ Steps to Bay & Museum subway stations

4.92 out of 5 average rating, 117 reviews

A cozy outdoor seating area features comfortable gray wicker furniture arranged around a wooden deck, with decorative flower boxes enhancing the backdrop. Surrounding greenery provides a serene atmosphere, complemented by clear blue skies and a nearby heating element for cooler evenings.

Apartment in The Beaches

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

4.93 out of 5 average rating, 55 reviews

A serene lakeside view features a deck with teal chairs positioned under a shaded pergola. Kayakers are seen enjoying the water, while a landscaped path lined with stones leads to the deck, offering a peaceful atmosphere for relaxation.

Home in Brampton

Modern Lakefront Cottage In The City With Hot Tub

Experience ultimate luxury at our Lakefront Mansion, a modern marvel with 4 bedrooms, 3.5 baths, and a wealth of amenities. From access to the beach at Professor's Lake Recreation Centre, to the entertainment haven with games and a bar, every moment promises excitement. Unwind in the hot tub, savor morning treats from the Nespresso machine, and marvel at the architectural grandeur. Perfect for family staycations and unforgettable events.

4.84 out of 5 average rating, 99 reviews

A private hot tub is illuminated in a calming blue light, situated against a backdrop of brick walls. Soft lighting enhances the intimate setting, while a window allows for views of the surrounding area.

Guesthouse in Port Perry

No-matata

Sit back and Enjoy a Peaceful getaway on Scugog Island. Star Gaze at night while soaking in private Hot tub. Fire pit, bbq, outdoor patio, fully equipped kitchen The property sits on 10 Acres of Land Pet friendly Snow mobile from Front Yard Dagmar Ski Resort 20 Minutes away Downtown Port Perry 10 Mins away Blue Heron Casino 2 Minutes away Netflix

4.92 out of 5 average rating, 13 reviews

A spacious living area features a dark leather sectional sofa adorned with patterned cushions. A round coffee table sits at its center, showcasing a small potted plant. In the background, a dining table is set against a neutral wall, while the kitchen area is illuminated by recessed lighting.

Apartment in Bronte West

Lakeview Retreat | Cozy 3-Bedroom Home w/ Parking

Welcome to your perfect getaway! 🌊✨ This spacious basement unit 3-bedroom home offers stunning lake views and a peaceful retreat just minutes from Oakville’s top attractions. Whether you're here for a relaxing escape, a family vacation, or a work trip, you'll love the modern comforts and serene surroundings this home provides.

4.77 out of 5 average rating, 79 reviews

A serene beach scene is depicted, showcasing gentle waves lapping at the sandy shore. Lush trees frame the view, providing a contrast to the clear blue sky and vibrant water. Traces of footprints can be seen in the sand, inviting a sense of tranquility.

Home in Pickering

Beach House: First Floor

Have fun with the whole family at this stylish place. It's a beach side custom made luxury house where you can enjoy sunrise and sun set view with Bar, Restaurant, Park, Public transport, Shopping Mall and many other amenities are just one step away. Its bright, specious and peaceful accommodation.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Pickering vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pickering's top sights

Toronto Zoo232 locals recommend

University of Toronto Scarborough16 locals recommend

Scarborough Bluffs Park94 locals recommend

Toronto Zoo station213 locals recommend

Deer Creek Golf Club11 locals recommend

Swiss Chalet46 locals recommend

Other great vacation rentals in Pickering

An open kitchen and living area is presented, featuring sleek, modern cabinetry and appliances. A dining table with seating for four is visible, alongside a black leather couch. Natural light filters through large windows, highlighting the warm wooden flooring and decorative green plants.

5 out of 5 average rating, 6 reviews

The Snug 1+1 Suite w/ Free Parking

4.75 out of 5 average rating, 4 reviews

The kitchen features modern cabinetry and a sleek countertop made of speckled granite. Stainless steel appliances include a refrigerator, oven, and dishwasher. A coffee maker is positioned for easy access, and natural light filters through the window above the sink.

Home in Brampton

My Charming Getaway

A spacious balcony offers sweeping views of downtown Toronto, showcasing urban landscapes and distant skyline features. Large glass panels create an unobstructed line of sight, while the building's modern architecture is evident in the design. Bright blue skies complement the cityscape.

4.81 out of 5 average rating, 83 reviews

Stylish Condo Heart of Downtown

5 out of 5 average rating, 3 reviews

The modern kitchen features stainless steel appliances and quartz countertops, complemented by an island with seating. A dining area is situated nearby, illuminated by natural light from large windows adorned with horizontal shades. Light wood flooring enhances the contemporary design.

Home in North York

Modern Home with Pool & Jacuzzi [no cleaning fee]

A modern living area features a cozy gray sofa adorned with soft cushions and a textured throw. A sleek entertainment center holds a 55" smart TV. Large windows provide panoramic views of the city, while light streams in, creating a bright atmosphere.

5 out of 5 average rating, 14 reviews

Bright & Stylish Suite | Prime Location + Parking

4.91 out of 5 average rating, 11 reviews

A spacious living area is captured from a high angle, featuring a large window allowing natural light to fill the room. A dining area and modern kitchen with dark cabinetry are visible in the background, while a potted plant adds a touch of greenery.

Home in Courtice

New Family Friendly Detached Home in Courtice

4.85 out of 5 average rating, 33 reviews

A modern living area is showcased, featuring a neutral-colored sectional sofa adorned with decorative pillows. A round coffee table sits in front, complemented by a potted plant and soft rug. Floor-to-ceiling windows allow natural light and provide a view of the cityscape.

Apartment in Fort York

Amazing Condo Heart of Downtown + 1 Free Parking