
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.

Private Suite in New Custom Home with Private Pool
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!

The Penty: Luxurious Penthouse with Pool, Hot Tub
Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

SpectacularPenthouse VIEWS/ POOL /free Parking
Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

Corner Unit in Liberty Village (Parking + Balcony)
Free parking available+ Close proximity to Budweiser Stage. Located in Liberty Village - one of Toronto’s most sought-after neighborhoods - this corner unit is a place to live, work, & play. The spacious, 700 sq ft layout offers 270-degree views of the city and Lake Ontario. With floor-to-ceiling windows, this 1 Bedroom + Den is flooded with natural light and zero wasted space. Enjoy a morning coffee or watch the sunset over cocktails on either of the two walk-out balconies.

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins
1,Welcome to my home in the heart of midtown Toronto in the Yonge & Eglinton area! It sleeps three guests comfortably and is an excellent base for your Toronto adventures! 2,With excellent access to public transportation, you can be in downtown within 15 minutes; you are a 5-minute walk from Eglinton Subway Station, 2 mins from TTC, and within walking distance to tons of shops and restaurants. 3,Loblaws (grocery) & LCBO (liquor) on the main floor of the building.

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.

Cozy Condo Next to CN Tower
Experience the best of Toronto in our modern one-bedroom plus one sofa bed condo, ideally located in the vibrant heart of the city. Enjoy breathtaking views from a high floor, offering a perfect retreat for urban explorers and business travelers. With easy access to top attractions, including the iconic CN Tower, and excellent commuting options, our condo combines comfort with convenience, making it the ideal base to discover Toronto's charm and energy.

King West Triplex Main FLR PVT APT 1 BDRM Parking
KING WEST TRIPLEX Mainfloor unit is overlooking the Park and has a Pool in front, baseball and tennis courts, ping pong table and enclosed Dog Park! Hardwood floors, 12ft ceilings, private parking in the rear and a private back patio. Pets permitted. Two blocks from King and Bathurst, club, bars/patio restaurant district, and grocery store. Long term: Request 31 nights or more to avoid paying an additional 13% tax.

Pool/ King Bed/Wifi/Toronto LakeView/Free Parking
The Shopping & Dining Retreat Shop, dine, and relax in style. This chic 1-bedroom condo features high-end décor, a queen pull-out sofa, and a full kitchen. 🛍️ Just steps from a vibrant mall and countless restaurants. 🚆 Toronto is only 23 minutes away via GO. Perfect for weekend getaways, foodie trips, or retail therapy. Secure your dates now and enjoy the ultimate mix of comfort and city convenience!

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Condo in Heart of Mississauga
Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

The Snug Oasis - Burrow (Near Airport)
Make some memories at this enchanting, family-friendly ranch style estate. Welcomed by old Oak trees and classic stone facades, your suite is on the ground floor. A warm wooden chamber abundant in antique charm, it overlooks the gorgeous garden and resort size pool. Birds chirping, bunnies visiting; nearby restaurants and poolside barbecues make it the perfect retreat!
Popular amenities for Pickering rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Cozy 2 bed Condo Near Scotiabank/Rogers/Union

Seraya Wellness Retreat

Home away from home with a hot tub and pool

Ravine Paradise ! heated pool and hot tub!

Countryside walk-out with pool.

The Ridge Roost - Uxbridge Township

Chic King West Studio – TIFF & FIFA at Your Door
Condo rentals with a pool

Downtown Markham Unionville

Stylish Downtown Toronto Condo with Free Parking

Large & Bright 2BR+Den in Midtown w/ Free Parking

Lakeside Downtown Condo for upto 4 ppl

Stylish 1+1 Corner Suite |Steps to Lake&Downtown

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Luxury Downtown Condo For 6 (Near CN Tower)

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Other vacation rentals with a pool

Rare 1BR - Rooftop Pool, Next to MTCC & CN Tower

Private Terrace & Pet Welcome, with Gym & Pool

Bright & Airy Condo Near the Water +1 Free Parking

Private 1 bed/1.5 bath in-law suite in a house!

Elegant & Modern Condo

Modern Designer Suite w/ Lake & City Skyline Views

Resort Style Lake View Condo

Oasis by the Lake
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,198 ZAR | R3,277 ZAR | R3,246 ZAR | R3,341 ZAR | R2,482 ZAR | R2,323 ZAR | R2,482 ZAR | R2,880 ZAR | R2,625 ZAR | R2,355 ZAR | R2,259 ZAR | R2,132 ZAR |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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 R318 ZAR 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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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall
- Downsview Park
- Christie Pits Park




