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Vacation rentals with a pool in Pickering

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pickering

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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.
Home in Scarborough
4.94 out of 5 average rating, 124 reviews

Modern Custom Built Walkout to Marble Pool Game RM

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

Top guest favorite
A well-lit bedroom features a spacious bed with neatly arranged towels. Two nightstands flanking the bed hold lamps. A desk and chair are positioned by the window, complemented by greenery. A large mirror and a TV are mounted on the wall, enhancing the relaxed atmosphere.
Condo in Entertainment District
4.98 out of 5 average rating, 103 reviews

Luxury Downtown Condo For 6 (CN Tower View)

Luxury awaits in our sophisticated 2bed, 2bath condo in the Entertainment District. This prime location places you steps away from Toronto's CN Tower, Metro Convention Centre, Rogers Centre, Hockey Hall of Fame & Scotia Bank Arena. Within a short walk, explore plenty of top dining, shopping, and entertainment options. Our unit is meticulously designed for modernity, elegance, and a truly relaxing experience. Enjoy our updated balcony with seating arrangements & breathtaking CN Tower views.

Guest favorite
A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.
Guest suite in Scarborough
4.9 out of 5 average rating, 105 reviews

Private Bluffs Suite | Pool | Pet-Friendly, Trails

Enjoy this beautiful, private, sun-filled suite with a large secluded yard and pool in a safe, upscale and serene forested neighborhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles and an EV charger (Tesla/J1772).

Guest favorite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.98 out of 5 average rating, 557 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Top guest favorite
A spacious living area features light wood flooring and large windows allowing natural light to fill the space. A comfortable sectional couch is arranged with wooden chairs and tables. A ceiling fan offers a cooling breeze, while lush greenery is visible outside through the windows.
Guest suite in Lorne Park
4.92 out of 5 average rating, 166 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

Top guest favorite
The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.
Apartment in Newmarket
4.99 out of 5 average rating, 199 reviews

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Top guest favorite
A spacious living room features a modern sectional sofa with decorative pillows, accompanied by a round coffee table atop a patterned area rug. Large windows offer skyline views, while vibrant artwork adorns the wall, adding a pop of color to the neutral decor.
Condo in Entertainment District
4.98 out of 5 average rating, 130 reviews

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

Enjoy your luxury condo in heart of Entertainment District. Best location in the downtown! Very close to all major attractions but silence and comfortable to enjoy city life. Breathtaking view, step away from CN Tower, Aquarium, Metro Convention Centre, Rogers Centre, TiFF, Union Station, Scotiabank Arena, Lake Ontario and others Outdoor pool in 15th floor with CN Tower view (seasonally open), gym area with new equipments, hot tub, steam room and other amenities ready for your leisure

Guest favorite
The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.
Villa in North York
4.94 out of 5 average rating, 194 reviews

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Top guest favorite
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
4.94 out of 5 average rating, 235 reviews

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

Top guest favorite
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
4.99 out of 5 average rating, 170 reviews

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub

Unwind in style at our year-round heated pool & soothing hot tub—the heart of this luxury 4-bed family oasis. Inside you’ll find plush beds, smart TVs, speedy Wi-Fi and a fully stocked chef’s kitchen. Outside, enjoy the fenced backyard with BBQ, lounge seating and night lighting. Pool & hot tub open 365 days Baby gear: crib, high-chair, safety gates Games galore: board games, books & playroom Seconds to beaches, shops and dining—yet peaceful enough for stargazing.

Guest favorite
A bright living area features a modern orange sectional sofa and a wooden coffee table. Large windows offer views of the cityscape. A dining area with high chairs is positioned beside a compact kitchen, with red cabinetry adding a pop of color.
Condo in Entertainment District
4.88 out of 5 average rating, 149 reviews

Beautiful Condo Across CN Tower and MTCC

A newly-furnished condo located at the heart of Downtown Toronto guaranteed to maximize your stay with everything at close proximity. This condo has 10 ft ceilings and over 700 sq ft We provide High-speed WiFi, Cable TV, washing machine/dryer, and basic amenities. Explore Toronto right at your doorstep: - Metro Toronto Convention Centre 30m - CN tower/Rogers Centre 210m - Union Station 500m - Harbourfront Centre 700m - Air Canada Centre 900m - TIFF Bell Lightbox

Guest favorite
A modern high-rise condominium building is visible, featuring a sleek façade of glass and metal. The surroundings include various city structures and signage, with a mix of urban architecture and a cloudy sky above.
Condo in Entertainment District
4.94 out of 5 average rating, 154 reviews

Luxurious heart of downtown condo next to CN Tower

Welcome to the heart of the city! A non-shared 1-bedroom condo with a full-sized kitchen. My condo is located just across the street from the CN Tower admission booth. 5-10 minutes walking distance to the Aquarium, Rogers Center, Air Canada Center, and Union Station. A few blocks from the entertainment district, endless dining, and shopping options. Fashionably furnished and decorated to be your perfect home away from home.

Popular amenities for Pickering rentals with a pool

When is the best time to visit Pickering?

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Avg. priceﺩ.ﺇ738ﺩ.ﺇ757ﺩ.ﺇ749ﺩ.ﺇ771ﺩ.ﺇ573ﺩ.ﺇ536ﺩ.ﺇ573ﺩ.ﺇ665ﺩ.ﺇ606ﺩ.ﺇ544ﺩ.ﺇ521ﺩ.ﺇ492
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Quick stats about vacation rentals with a pool in Pickering

  • Total vacation rentals

    Explore 50 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 800 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Pickering vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pickering rentals

  • 4.8 Average rating

    Pickering stays are highly rated by guests—averaging 4.8 out of 5!

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