Vacation rentals with a pool in Whitby

Find and book unique homes with a pool on Airbnb

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Popular amenities for Whitby rentals with a pool

House rentals with a pool

Guest favorite
Home in Ajax
4.92 out of 5 average rating, 39 reviews

Beautiful Cottage in Ajax

MargaritaRating, 5 stars1 month ago
The place is really spacious! The jacuzzi being inside the house was a huge plus - we loved being able to use it during the winter. Based on the photos, we thought only two couples would need to share a room, but there were actually three beds in one room. Other than that, it was an amazing stay! The kitchen had everything we needed, and the living room was lovely, complete with Christmas decorations, which I thought was a very sweet touch. The host was super nice and accommodating. Overall, I highly recommend this place!
Guest favorite
Home in Port Perry
5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

AndreaRating, 5 stars5 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.
Guest favorite
Home in Scarborough
4.98 out of 5 average rating, 41 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

ElenaRating, 5 stars1 month ago
Great stay in beautiful cozy home. We appreciated the Christmas decorations.
Superhost
Home in Oshawa
4.76 out of 5 average rating, 21 reviews

PS4 + BBQ: 5 Bedooms, 3 Bathrooms - 2 Units in 1!

RowenaRating, 5 stars1 month ago
Nice place and suited our large grp well with the 5 bedrooms and 3 bathrooms. Would love to stay on the summer and hang around the pool!
Superhost
Home in Scarborough
4.91 out of 5 average rating, 67 reviews

Ravine Paradise ! heated pool and hot tub!

ChanthruRating, 5 stars1 week ago
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.
Guest favorite
Home in Uxbridge
5 out of 5 average rating, 31 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

MustafaRating, 5 stars4 days 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, 12 reviews

Luxe, Family-Friendly Oasis Home With Pool

SandyRating, 5 stars3 months ago
We had a great stay at this beautiful home in Toronto, the location was awesome and the neighbourhood was quiet and lovely. Then home is exactly as described, with really super bedding (which is one thing that is very important to me). Amazing household supplies available at our arrival and for our stay. The owner was extremely helpful with all of our questions and super friendly and responsive. The back yard is amazing!! The pool was closed for our stay as it was November; but we enjoyed sitting outside enjoying the fresh air…. As the outdoor sitting area is amazing!! Very resort vibe!! Our favourite space was the kitchen area…. Very well designed with everything you could need. Also great lighting inside the home with dimmers - which is also a special addition that I appreciate. It was a very enjoyable stay and a nice break from downtown Toronto …. But still close to lots of shopping and the motorways. And close to public transport if needed. I would def recommend to anyone…….
Guest favorite
Home in Scarborough
4.95 out of 5 average rating, 97 reviews

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm

AdrianaRating, 5 stars1 month ago
Very nice house. It was just like the pictures and it had everything we needed. It’s located in a convenient area not too far from the downtown area. Our host was very nice and quick to respond through the app. She let us check-in earlier which was super convenient and helpful. Natalie was very welcoming of our two dogs which is always appreciated. The only problem we encountered was that the sofa bed was broken so it was uncomfortable to sleep a whole night in it. Luckily we only needed it for 2 out of 5 nights. I’m sure they’ll fix it before the next guest comes. Thank you!

Condo rentals with a pool

Superhost
Condo in Downtown Toronto
4.87 out of 5 average rating, 118 reviews

2 Bedroom CN Tower Waterfront Oasis w Parking

JohnRating, 5 stars3 weeks ago
My friend and I drove in from out of town to attend the last two Sum 41 shows and a Maple Leafs hockey game. Mohammed’s unit was GORGEOUS with city skyline views in all directions! Our proximity to Scotiabank Arena and other major venues was second to none! I highly recommend if you are attending events nearby. Mohammed provided clear instructions on how to check in and out of the unit. The unit was very clean and contained everything we needed to make our stay worry free. Mohammed was very responsive to questions when asked. We were able to extend our time in Toronto by a day and Mohammed responded within minutes to approve availability. Thanks to Mohammed for making our first trip to Toronto a memorable one! We will be back!
Guest favorite
Condo in Fort York
4.96 out of 5 average rating, 130 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

JennyRating, 5 stars3 months ago
We stayed here while in town to see Taylor Swift. The location was an easy and safe walk to Rogers Centre and the CN Tower. We had no issues getting a 4am Uber to the airport at this location. Jessica was very friendly and accommodating to an early check in. I asked several questions in the weeks leading up to our stay and she always answered quickly and thoroughly. I’m so sad our plans only had us in the AirBnb for a few short hours because it was absolutely lovely with amazing views of the city. We loved the city and hope to return—we will absolutely stay here again!
Guest favorite
Condo in Downtown Toronto
4.89 out of 5 average rating, 178 reviews

Luxury 1+Den condo steps away from CN Tower & Lake

FatemehRating, 5 stars2 months ago
amazing view, very convenient location. very clean and kitchen fully stocked
Superhost
Condo in Downtown Toronto
4.87 out of 5 average rating, 325 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

IsabellaRating, 5 stars2 months ago
I had an amazing stay at this Airbnb! The space was spotless, beautifully decorated, and exactly as described. The host was incredibly welcoming, responsive and extremely helpful. The self check-in was a breeze, the location was perfect and was a walkable distance to Union. Highly recommend this place for anyone visiting!
Guest favorite
Condo in Downtown Toronto
4.92 out of 5 average rating, 77 reviews

Luxury Designer Condo, steps to CN tower

AljosaRating, 5 stars2 weeks ago
Awesome Stay!!! The Host was super responsive and helpful, the place was very clean and easy to check into. No issues at all, would definitely stay here again!
Superhost
Condo in Fort York
4.83 out of 5 average rating, 109 reviews

Luxury Condo with Parking. CN Tower + Lake View

KeandreRating, 5 stars1 week ago
I originally booked Prathaben’s Airbnb for four nights but ended up extending my stay for an extra night—simply because I couldn’t get enough of the breathtaking views! Waking up to a stunning panorama of the water and the CN Tower/downtown skyline was an experience in itself. The space was clean, comfortable, and exactly as described, with everything I needed for a seamless stay. Prathaben was a fantastic host—responsive, accommodating, and helpful. Whether you’re in Toronto for business or leisure, this Airbnb is a perfect choice. I’ll definitely be returning!
Superhost
Condo in Downtown Toronto
4.78 out of 5 average rating, 123 reviews

Home away from home Master King w Parking

EmiRating, 5 stars1 month ago
The location was wonderful, and the place was safe, clean, and very relaxing. The location was wonderful, and the place was safe, clean, and very relaxing. I definitely recommend it! I stayed here when I traveled to Canada with my daughters, and it was really great! Highly recommended!
Guest favorite
Condo in Downtown Toronto
5 out of 5 average rating, 117 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

MattRating, 5 stars3 weeks ago
I had a fantastic experience at this Airbnb! The hosts were incredibly welcoming and communicative, making the whole booking and check-in process smooth and easy. The location was perfect. The condo itself was spotless and comfortable, with all the amenities I needed for a great stay. I’d absolutely stay here again and highly recommend it to anyone visiting the area!

Quick stats about vacation rentals with a pool in Whitby

  • Total rentals

    20 properties

  • Total number of reviews

    270 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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