Holiday 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 favourite
Home in Port Perry
5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

AndreaRating, 5 stars9 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 favourite
Home in North York
5 out of 5 average rating, 13 reviews

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars2 weeks ago
My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!
Top guest favourite
Home in Scarborough
4.98 out of 5 average rating, 48 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars1 week ago
We had a delightful stay at Jasmine’s place. The space was impeccably clean and thoughtfully decorated, making it feel like a true home away from home. Jasmine was an exceptional host—attentive, communicative, and always ready with helpful replies with my questions. I highly recommend her place to anyone visiting the area and would love to return in the future.
Superhost
Home in Scarborough
4.92 out of 5 average rating, 75 reviews

Ravine Paradise ! heated pool and hot tub!

CelesteRating, 5 stars2 weeks ago
this was one of the best airbnbs we stayed at. the place was clean and even more beautiful than described. Preston communicated with me months before we rented, through tech difficulties, before during and after the stay. they were understanding, courteous, and helpful. would stay here again, even my sister who visited inquired for the future.
Guest favourite
Home in North York
5 out of 5 average rating, 15 reviews

Luxe, Family-Friendly Oasis Home With Outdoor Pool

RonaldRating, 5 stars2 weeks ago
Ali is an amazing host. We booked pretty last minute and Ali was understanding and worked with us. He’s very proactive and reached out to make sure everything is alright during the stay. His property was spotless and everything needed was provided. It was perfect for 4 adults and 2 toddlers. With room for another 2 adults if needed. My kids enjoyed the pool the most, it had a raised area where the kids could walk and splash around, while the other end was deep enough for adults to have a good swim. The rest of the property felt very luxurious and high quality. Check in was a breeze and checkout was just as quick. We hope to deal with Ali in the future if possible.
Guest favourite
Home in North York
4.85 out of 5 average rating, 75 reviews

Toronto Pool Retreat

JasonRating, 5 stars3 weeks ago
Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.
Superhost
Home in Cedar Valley
5 out of 5 average rating, 5 reviews

Forest House | Golf/Hiking/Horse Riding Nearby

BrandonRating, 5 stars2 weeks ago
Had a really good time here place was beautiful. Would defiantly recommend if your looking for a weekend get away!! Hosts went above and beyond to make sure our stay was amazing.
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

JessieRating, 5 stars1 month ago
What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.

Apartment rentals with a pool

Superhost
Apartment in Davisville Village
4.85 out of 5 average rating, 105 reviews

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

SohyeonRating, 5 stars1 week ago
place is quite walkable. even so quiet area.
Superhost
Apartment in Downtown Toronto
4.85 out of 5 average rating, 163 reviews

1 bdrm Condo across CN Tower at 39 FLR Stun. View

PremRating, 5 stars1 month ago
Location was perfect. Everything thing is nearby. Perfect view of sunset. Just had a little issue with internet connectivity on the tv and the remote control “OK” button doesn’t work well so you kinda have to press down hard. Overall, the place was nice and clean. Would definitely recommend to stay here.
Superhost
Apartment in Downtown Toronto
4.89 out of 5 average rating, 101 reviews

Beautiful Condo Across CN Tower and MTCC

Daniela Rating, 5 stars5 months ago
I really enjoyed staying at William’s airbnb. Host was always responsive, professional and nice. The instructions were clear and easy to follow. Really recommend it!
Top guest favourite
Apartment in Fort York
4.98 out of 5 average rating, 192 reviews

Stylish Downtown Toronto Condo with Free Parking

NickRating, 5 stars6 days ago
Great place and location. As described, no issues and responsive host.
Guest favourite
Apartment in Downtown Toronto
4.97 out of 5 average rating, 245 reviews

Chic, High-Rise Apartment with CN Tower Views

KevinRating, 5 stars2 weeks ago
We were in town to attend a couple Jays games and see DT Toronto. This location was great for both. Also easy access to Union station. Condo was just right for us.
Top guest favourite
Apartment in Downtown Toronto
4.97 out of 5 average rating, 128 reviews

Trendy King West townhome

PaulRating, 5 stars1 day ago
Karina’s apartment is really spacious and nice. I love it when it is stocked with everything you need. Very spacious as well and the bed is the most comfortable ever! Karina is super responsive and helped me with everything! Definitely recommend!!
Guest favourite
Apartment in Downtown Toronto
4.92 out of 5 average rating, 133 reviews

Luxurious heart of downtown condo next to CN Tower

AllisonRating, 5 stars2 weeks ago
Had a great stay. Condo was clean and in a great location to walk anywhere downtown.
Guest favourite
Apartment in Fort York
4.98 out of 5 average rating, 121 reviews

Artsy and Comfy Home with a View

YomiRating, 5 stars1 week ago
Great Location if you're visiting the city close to everything downtown. Great view as well being on the 20th floor. Very clean apartment. The host used white sheets, pillowcases and towels which is always a plus in my opinion. Free parking was a HUGE plus for me (Parked my car and walked everywhere). I would definitely stay again and would recommend to anyone.

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

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

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