
Holiday 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.

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!

Prestigious Bluffs Private Guest Suite
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).

Luxury Stay w/phenomenal view!
Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

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

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.

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.

The Fort York Flat
Welcome to the Fort York Flat! This 2 Bedroom, 1 Bathroom space has been thoughtfully renovated using a mixture of modern and contemporary decor to create a relaxing, upscale place to kick back while enjoying everything Downtown Toronto has to offer. Our location and smart lockbox located at the front doors makes checking into the flat easier than ever, no need to worry about fussing with the front desk staff or waiting for elevators.

Entire Unit - CN Tower View - Lux. 1 BR DT Condo
PLEASE SEND ME A MESSAGE FIRST BEFORE MAKING ANY BOOKING REQUESTS. A 10 ft ceiling modern and stylish condo offering stunning CN Tower views. The suite is located right across CN Tower, Rogers Centre, Metro Convention and Ripley's Aquarium. The prime location will help you maximize your stay to explore Toronto, enjoy sports events, or attend meetings within walking distance. We provide Wifi, Cable TV , washer/dryer, and paid parking.

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.

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
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.

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE
This beautiful modern 1 bed & q bath suite is located in the heart of downtown Toronto's Entertainment & Financial District - in the prestigious 300 Front Street building in the core of the city. Enjoy a nice dinner on the balcony with a lake and CN Tower view! The building has a fully equiped Fitness center, Outdoor Pool with a 360 degree of the whole city, Steamroom, Whirlpool BBQ
Popular amenities for Pickering rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Seraya Wellness Retreat

Award Winning Luxury Home with Heated Pool + Sauna

Home away from home with a hot tub and pool

Luxury Spa Escape with Pool & Jacuzzi

Ravine Paradise ! heated pool and hot tub!

The Ridge Roost - Uxbridge Township

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

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

Beautiful Condo + CN Tower View + Free Parking

Beautiful Condo Across CN Tower and MTCC

Luxury Condo with FreeParking. CN Tower Lake View

Luxury Designer Condo, steps to CN tower

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

Luxury Downtown Condo For 4 (CN Tower Views)

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Other holiday rentals with a pool

Spectacular Stay with CN Tower View!

The King's Rest

Bright Sun Filled Condo + Pool + Gym, CN Tower

Tranquil Lakeside Suite Toronto

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

Penthouse 2BR+Den | Skyline Views • SQ1 • Parking

Luxury Penthouse Suite SQ1

Elegant King Suite w/ Skyline Views, Pool & Gym
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 170 | € 175 | € 173 | € 178 | € 132 | € 124 | € 132 | € 153 | € 140 | € 125 | € 120 | € 114 |
| 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 holiday rentals with a pool in Pickering

Total holiday rentals
Explore 50 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at € 17 per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Pickering holiday rentals include wifi 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
- Port Credit
- Distillery District
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Downsview Park
- Toronto City Hall
- Christie Pits Park




