Vacation rentals with a pool in Pickering

Find and book unique homes with a pool on Airbnb

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Popular amenities for Pickering rentals with a pool

House rentals with a pool

Guest favorite
Home in Mississauga
4.94 out of 5 average rating, 16 reviews

Luxury House with a Bright Sunroom & a heated pool

MarianneRating, 5 stars1 week ago
We had a wonderful stay. Everything was up to standard. House was clean and well set up.
Guest favorite
Home in Port Perry
5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

AndreaRating, 5 stars7 months ago
While journeying from the UK to Port Perry, we were fortunate to stay at the Horse Farm Luxury Estate for a week in September. Situated next to a riding school, the tranquil area was perfect for relaxation. Horses grazed in the paddock beside the house – their beauty admired from a distance as per the rule 'do not touch the horses'. The house's position was ideal for exploring the surrounding area, including Port Perry, with easy access to nearby highways for visits to Oshawa, Toronto, and even Niagara Falls. The spacious house had numerous amenities, such as a basement games room and a ground floor club area with a bar. A conservatory connected to a deck and hot tub. Anthony's great communication and assistance made our stay stress-free after a long journey. I highly recommend Horse Farm Luxury Estate for a comfortable stay in Port Perry.
Superhost
Home in Burlington
5 out of 5 average rating, 13 reviews

Modern Luxury House w/EV Charger & Heated Pool

DidiRating, 5 stars5 months ago
Our stay at this Airbnb in Burlington, Ontario, was truly a home away from home. From the moment we arrived, we felt completely at ease in this beautiful and peaceful space. The home itself is lovely, with warm, inviting decor and thoughtful touches that made us feel instantly comfortable. The location in Burlington was ideal for us as a family. We enjoyed exploring the nearby , taking peaceful walks along the waterfront, and visiting the local parks. Burlington’s small-town charm paired with its scenic beauty was a perfect match for our family’s needs. The hosts were exceptional—always responsive and so kind, which really enhanced our experience. They went above and beyond to ensure we had everything we needed, and their hospitality made us feel genuinely welcomed. We left with wonderful memories, and we wouldn’t hesitate to stay here again on future visits to Burlington. Highly recommended for families or anyone seeking a peaceful retreat in a beautiful area
Guest favorite
Home in Lakeview
4.88 out of 5 average rating, 25 reviews

Lakeside Luxury Retreat | Pool & Putting Green

MelissaRating, 5 stars2 months ago
Virinder was super responsive, and the place was lovely for our one night stay!
Superhost
Home in Newmarket
4.82 out of 5 average rating, 22 reviews

Cozy Pool house in Newmarket

FabrizioRating, 5 stars8 months ago
Great stay. Brought the family there for a weekend of pool fun. My kids are 3 and 16 months. Minoo is a great host and very responsive. The home is meticulous but not particularly kid friendly - she was upfront and described this to me in advance. If you have a little one that likes to explore on their own - you need to keep an eye on them, lots of little decorations at arms reach for the kids. Spiral staircase can be difficult to use with kids in your arms as well. Pool was beautiful and warm however is not a walk in and the shallow end is a third of the pool. We spent most of our time in the private backyard or out for walks. Local parks and amenities close by. We had a great time and would absolutely stay at Minoos place again when visiting Newmarket. Thanks for the hospitality Minoo !!
Guest favorite
Home in Uxbridge
5 out of 5 average rating, 31 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

MustafaRating, 5 stars2 months ago
An incredibly cozy and clean retreat, me and my friends could not have asked for a better weekend escape. Close to ski resorts while also being close to the city and infrastructure, this place is incredible value! But most of all Youseff and his son are so helpful, amazing hosts ❤️
Guest favorite
Home in North York
5 out of 5 average rating, 13 reviews

Luxe, Family-Friendly Oasis Home With Pool

SergeRating, 5 stars4 months ago
Great place with all the amenities for a family of 5. Easy access from airport. Great host that was responsive throughout our stay. Would highly recommend.
Guest favorite
Home in Niagara
4.91 out of 5 average rating, 302 reviews

King West Victorian Studio Gem

JoelRating, 5 stars6 days ago
Kathleen's place was great, exactly as advertised. I really appreciated how tidy and well stocked the suite was. A great place to stay.

Condo rentals with a pool

Superhost
Condo in Downtown Toronto
4.88 out of 5 average rating, 123 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

RebeccaRating, 5 stars1 month ago
Place was a perfect spot for a quick night in Toronto watching the leafs game! It had so many amenities available - great views! Check in is a little complex because of the up and downs to get the keys / parking fob but as soon as you have your bearings of all the elevator locations it’s pretty smooth! Worth it for free parking! Enjoyed the place!
Guest favorite
Condo in Fort York
4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

StephanieRating, 5 stars1 month ago
Jessica was one of the best Airbnb hosts I’ve had in a long time! I celebrated my three-year anniversary here with my partner, and it was absolutely perfect. Jessica went above and beyond by setting up the room beautifully with flowers, rose petals, and electric candles—my partner was overjoyed. She was incredibly accommodating, allowing us to check in early and responding quickly to all my requests. The space itself was spotless, smelled amazing, and was incredibly comfortable. As a same-sex couple, safety is always a consideration when booking accommodations, but this location felt extremely secure. My partner and I were out late at night and felt completely at ease. The apartment has a double lock for added security, and the building itself is well-monitored. On top of all that, the view of downtown and the CN Tower was stunning. I highly recommend this stay, especially for couples—10/10!
Guest favorite
Condo in Fort York
4.97 out of 5 average rating, 116 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

RiaRating, 5 stars6 days ago
The apartment was lovely... Just perfect for us... We were a couple... It was self contained so we had everything we needed. Very clean... Secure as you need a key or code to enter... Nice location. Our hosts were the best. They were helpful from start to finish. Any questions were quickly answered. We did not meet in person but we felt like we did as we were in constant contact. It's close to downtown Toronto. We had a parking spot assigned to us. This made it so much nicer. We just had to take the elevator to get to "our home away from home". We had access to a pool and hot tub on the floor but did not have the time to see or use it.
Guest favorite
Condo in Fort York
4.89 out of 5 average rating, 414 reviews

Lakeside Condo Studio In Downtown Toronto

IeishaRating, 5 stars3 weeks ago
Very clean and great locations for nights in downtown Toronto
Guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 151 reviews

3BR Rooftop Pool-Gym-Steps-MTCC-CN Tower-Parking

OnaRating, 5 stars1 week ago
The absolutely perfect spot for a quick Toronto vacation! Loved the space, and Matthew’s instructions for check-in, parking, etc. were fabulous.
Top guest favorite
Condo in Fort York
4.98 out of 5 average rating, 187 reviews

Stylish Downtown Toronto Condo with Free Parking

BridgetRating, 5 stars4 days ago
Honestly, this was the best AirBnB I have stayed at. Super clean, beautifully decorated, well equipped, super soft sheets on an extremely comfortable bed - there is not anything I would say I wished were different. The location is a bit on the outskirts, but I really enjoyed the walk to get further into the action. There was no issues with noise/neighbors. Loved it and will definitely try to book again if I’m headed to Toronto.
Guest favorite
Condo in Fort York
4.88 out of 5 average rating, 32 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

JordanRating, 5 stars3 weeks ago
Great condo in a great location. Lovely view of Toronto. Walking distance to all amenities.
Top guest favorite
Condo in Downtown Toronto
5 out of 5 average rating, 126 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

BrianRating, 5 stars4 days ago
I really enjoyed our stay here. The unit was exactly how it was described and shown in the pictures. Check in and out went very smoothly. The location was the best of all. The Rogers centre is pretty much right across the street if attending another Roger centre event, I will definitely Stay here again.

Quick stats about vacation rentals with a pool in Pickering

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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