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 private heated pool is framed by stone tiles and lush greenery, reflecting sunlight. Large glass doors lead into the home, enhancing the outdoor connection. Seating areas are available nearby, surrounded by natural landscaping and elevated steps leading to the indoor space.

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

An open-concept living space is showcased, featuring a cozy sectional sofa facing a flat-screen TV. A dining area with a glass-top table is paired with modern white chairs. The kitchen, equipped with contemporary appliances, is seamlessly integrated into the area, creating a welcoming and functional atmosphere.

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

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.

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, 73 reviews

A scenic view of the lake is visible through a glass door, with outdoor seating arranged on a wooden deck. Two blue chairs face the water, while a round white table and chairs are positioned nearby, creating a serene space for relaxation.

Cottage in Barker

Lake Front Vista & HotTub w/Sun-Thu night discount

Enjoy Spectacular Lakefront views. Relax at your own pace. Take a dip in the spa tub or just enjoy the scenery Very quiet road Speedy internet Fire-pit Enjoy the Niagara Wine Trail 2 Bdrm 6 min to Golden Hill Park 12 min to White Birch Golf course 15 min to Olcott/Burt (fishing charters) 20 min to Waterport/Kent (fishing charters) 50 min to Niagara Falls *Promo: 3rd night or more, will be discounted ~25% (no discount on cleaning and fees, excl 06/23-09/10)

Cottage in Little Britain

A tranquil deck area features comfortable seating with decorative cushions. A small table holds various plants, while the lush green surrounding trees provide privacy. The view beyond includes glimpses of the water, enhancing the serene outdoor environment.

4.8 out of 5 average rating, 30 reviews

Cozy Lakeview Cottage | Kawartha Lakes Getaway

Peaceful Atmosphere: Relax in serene surroundings with nature's soothing sounds. Water Access: Short stroll to the water's edge for swims, relaxation, kayaking, and ice fishing. Open Design: Cathedral ceiling, large windows, patio doors for deck access. Family Fun: Bunk beds, teepees, board games for kids' enjoyment. Scenic Views: Panoramic lake and field views from the spacious deck. Enjoy boho decor, coffee bar, firepit, WiFi.

5 out of 5 average rating, 41 reviews

Home in Uxbridge

Lakeside Lodge

Skiers dream. Close to Dagmar and Lakeridge ski resorts. Modern, fully renovated beautiful home/cottage. Make some memories at this unique and family-friendly place. Enjoy kayaking canoeing paddle boarding, fishing, outdoor fires, sunsets. Winter offers icefishing, close to ski hills with a warm fireplace to cozy up to after a day on the slopes.

4.84 out of 5 average rating, 98 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

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

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, 5 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.

4.8 out of 5 average rating, 82 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, 11 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

4.95 out of 5 average rating, 22 reviews

A light-filled living area is presented with pale blue walls and wooden flooring. Comfortable white seating is arranged around a coffee table, near a gas fireplace. A large television is mounted above the fireplace, and greenery is provided by potted plants in the corners.

Townhouse in Mimico

Modern Toronto Townhome by the Lake - Free Parking