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 Ajax
4.93 out of 5 average rating, 42 reviews

Beautiful Cottage in Ajax

PerryRating, 5 stars3 weeks ago
The house was unique and provided exactly what we were looking for. It had lots of open space and a great kitchen. We all really enjoyed our weekend stay. Thank you Sabesan
Guest favourite
Home in Port Perry
5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

AndreaRating, 5 stars6 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.
Top Guest favourite
Home in Scarborough
4.98 out of 5 average rating, 42 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

CarmalettaRating, 5 stars2 weeks ago
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
Superhost
Home in Newmarket
4.82 out of 5 average rating, 22 reviews

Cozy Pool house in Newmarket

FabrizioRating, 5 stars7 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 !!
Superhost
Home in Scarborough
4.91 out of 5 average rating, 67 reviews

Ravine Paradise ! heated pool and hot tub!

ChanthruRating, 5 stars1 month 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 favourite
Home in Uxbridge
5 out of 5 average rating, 31 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

MustafaRating, 5 stars1 month 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 favourite
Home in North York
5 out of 5 average rating, 12 reviews

Luxe, Family-Friendly Oasis Home With Pool

SandyRating, 5 stars4 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 favourite
Home in Scarborough
4.95 out of 5 average rating, 98 reviews

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

JoelleRating, 5 stars2 months ago
Absolutely amazing place and the host thought of everything from the travellers handbook about the property and restaurant close by to leaving the guest snacks and drinks in the fridge. The place is very much like the picture and I am definitely going to book again sometime soon so I can enjoy the property this coming summer. I highly recommend.

Condo rentals with a pool

Guest favourite
Condo in Downtown Toronto
4.88 out of 5 average rating, 101 reviews

2 beds-CN Tower View

JaziaRating, 5 stars3 weeks ago
Amazing stay in Toronto! The location couldn’t be better, everything is within walking distance, including great restaurants and a grocery store. The view from the unit is spectacular, making the stay even more enjoyable. Shahla was also very flexible with check-in, which made our arrival smooth and stress-free. Just a heads-up: you may want to bring your own amenities, but overall, highly recommend this place for anyone looking for a convenient stay in the city!
Guest favourite
Condo in Downtown Toronto
4.88 out of 5 average rating, 122 reviews

Downtown 2BR/2Bath Suite w/City+Lake Views+Parking

KarenRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Fort York
4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

StephanieRating, 5 stars3 weeks 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 favourite
Condo in Downtown Toronto
4.9 out of 5 average rating, 181 reviews

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

MarshaRating, 5 stars1 week ago
Such a great experience from start to finish. Stunning CN tower and water views. Amazing location- walkable to shows, games, shopping, restaurants. Starbucks attached to the building. We were a 6-8 min walk to both shows we attended during our stay (Royal Alexandra and Princess of Wales). Wellington Market was just 3 min walk away and was great for shops and food. Condo is well stocked with everything you need, including a washer and dryer. Lots of towels, linens and all the essentials! Check in and check out was easy! Hosts Kat and Dan were very responsive and helpful. Highly recommend. We would certainly love to stay here next time we visit!
Top Guest favourite
Condo in Fort York
4.97 out of 5 average rating, 114 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

Jennifer MarieRating, 5 stars1 month ago
Great place to stay in the heart of Toronto! It was close to everything including the CN tower. The hosts were great at communication and the place was adorable!
Guest favourite
Condo in Fort York
4.9 out of 5 average rating, 411 reviews

Lakeside Condo Studio In Downtown Toronto

CourtneyRating, 5 stars4 months ago
Kyrylo's condo was an extremely clean and functional little spot, comfortable for 2 people. Perfect location for if you're attending a concert at the Rogers Centre (about a 20 minute walk away). Kyrylo's instructions for checking in were so detailed and he was very responsive. From start to finish the whole experience was fantastic. Highly recommend!!
Superhost
Condo in Fort York
4.84 out of 5 average rating, 110 reviews

Luxury Condo with Parking. CN Tower + Lake View

DevinRating, 5 stars1 month ago
Amazing condo. The space is beautiful perfect for one or two travelers and the view of the CN tower was incredible. The building is very modern with a friendly staff and a beautiful gym/pool and sauna. I will definitely look forward to staying here again.
Guest favourite
Condo in Davisville Village
4.91 out of 5 average rating, 267 reviews

new penthouse one bedroom

ErichRating, 5 stars3 days ago
Great place to stay in midtown Toronto, close to public transport, foodmarket, pubs and restaurants.

Quick stats about holiday rentals with a pool in Whitby

  • Total rentals

    20 properties

  • Total number of reviews

    300 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

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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