
Holiday rentals with a pool in Whitby
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Whitby
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Whitby rentals with a pool
House rentals with a pool

Beautiful Cottage in Ajax
The only 4 star that was given was simply because the place was slightly more dated than advertised. Absolutely everything was wonderful and being "dated" had no effect on our stay - just a simple observation.

Horse Farm Luxury Estate
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.

Vacation Getaway with Heated Spa-Pool Open365 Days
I had an amazing experience staying at this beautiful home. The property was exactly as described, and even better in person! It was clean, spacious, and thoughtfully decorated, making it feel like a home away from home. The host was incredibly welcoming and responsive, ensuring that we had everything we needed for a comfortable stay. The location was perfect, with easy access to local attractions and amenities. I highly recommend this place to anyone looking for a relaxing and enjoyable stay. Can't wait to return!

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms
This house was beautiful! Comfortable and relaxing the master shower was to die for! On top of that jasmine and Keith really was proactive and attentive to us and whatever we needed they were able to supply us with and was really kind sweet and amazing couple to work with over all! Definitely will book here again

Ravine Paradise ! heated pool and hot tub!
Preston was a great host. The property is beautiful with a great view in the backyard. A very clean property as well. Preston was very accommodating, and very responsive. Definitely will book again.

Redwood Haven East: Your Dream Getaway in Uxbridge
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 ❤️

Luxe, Family-Friendly Oasis Home With Pool
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.

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm
In ALL honesty, this has been one of the best Airbnb experiences I have ever had! The attention to detail this place has is amazing! There was a wine bottle waiting for us, snacks, chocolate, water sooo much stuff. We arrived late and didn’t get a chance to buy anything on the way this saved us! Really wasn’t expecting that. Home is beautiful brand new, super clean! Quiet calm area, wasn’t able to use the pool since it’s cold out still but I will def want to be back here in Summer. Best of all pet friendly! Thank you for a great experience Natalie your a great host and thank you for allowing us to leave a little later due to our late check in. Such a great experience.
Condo rentals with a pool

Luxury Downtown 2Bed by ScotiaBank Arena + Parking
You cannot beat this location! The Airbnb exceeded our expectations. It was spacious with all the amenities you could want. An amazing space with spectacular views, and a patio to enjoy our time even more. Close to absolutely everything. We walked everywhere, took in a hockey game and felt like we were living in downtown Toronto. A perfect weekend getaway. Highly recommended!

Modern Downtown Condo Free Parking/ Walk to Lake
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!

Luxury 1+Den condo steps away from CN Tower & Lake
Katherine was super helpful and clear. She gave helpful recommendations and was always prompt when responding to questions. Thanks so much!

Luxury Waterfront Downtown Condo w/ Pool & Parking
We had a great stay. The place was clean and very nice. I love how parking was included with our stay. That was convenient. Highly recommend!

Lakeside Condo Studio In Downtown Toronto
Very clean and great locations for nights in downtown Toronto

Luxury Designer Condo, steps to CN tower
I loved being able to use the garage parking spot for our stay. We walked and took public transportation to see the city. The condo was well suited for our minimal needs. We enjoyed having two bedrooms rather than two beds in a single hotel room. The view was nice and gave a real big city vibe for us suburbanites.

3BR Rooftop Pool-Gym-Steps-MTCC-CN Tower-Parking
very clean apartment, walkable to everything, across the street from CN tower. Matthew was very proactive with communication. ours was kind of last minute reservation, but Matthew was very fast is getting back to us with confirmation and provided all the instructions for checkin. The apartment building has security and was fully gated, which made us feel very safe.

Luxury Downtown Condo For 6 (Near CN Tower)
Clean, very conveniently located, and always quick communication before and during the trip from Bri and Mike! Great set up for our family (2 adults and 2 kids). Would definitely stay here again if returning to Toronto.
Quick stats about holiday rentals with a pool in Whitby
Total rentals
30 properties
Total number of reviews
310 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- Budweiser Stage
- Port Credit
- University of Toronto
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- CF Toronto Eaton Centre
- Toronto Zoo
- Royal Woodbine Golf Club
- Massey Hall
- Jackson-Triggs Niagara Estate
- Harbourfront Centre
- Yonge-Dundas Square
- Trinity Bellwoods Park
- Royal Ontario Museum
- Riverview Park and Zoo
- Royal Alexandra Theatre
- BMO Field
- Dufferin Grove Park
- Markham Green Golf Club
- Casa Loma