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
An outdoor area features a gently curving pool surrounded by a spacious deck. A gazebo offers shaded seating, while decorative structures and planters add visual interest. Lush greenery borders the space, creating a calm and inviting atmosphere.
Home in Ajax
4.93 out of 5 average rating, 43 reviews

Beautiful Cottage in Ajax

StéphaneRating, 5 stars2 weeks ago
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.
Guest favorite
A clear blue pool is surrounded by a paved area, featuring several black lounge chairs positioned for relaxation. A green inflatable float rests in the water alongside a blue float. A wooden structure is visible in the background, providing additional amenities.
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.
Top guest favorite
A heated swimming pool surrounded by lush greenery reflects the clear sky above. The pool is framed by a glass fence and features colorful pool toys floating on the surface. A pergola provides shaded seating along the spacious deck, inviting outdoor relaxation.
Home in Scarborough
4.98 out of 5 average rating, 43 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

CarmalettaRating, 5 stars1 month 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
The serene pool area is illuminated by soft fairy lights, creating a calming atmosphere as the sun sets in the background. Multiple lounge chairs are positioned around the pool, offering a perfect spot to relax and enjoy the scenic views of the surrounding nature.
Home in Scarborough
4.91 out of 5 average rating, 67 reviews

Ravine Paradise ! heated pool and hot tub!

ChanthruRating, 5 stars2 months 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
The heated pool is enclosed by a metal fence and features a playful inflatable float. Sun loungers are placed under colorful umbrellas, while a grassy area and trees provide a natural backdrop. A distant view of blue buildings and a hillside completes the scene.
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
A private backyard features a heated saltwater pool with a waterfall, surrounded by lush greenery. A covered gazebo offers seating options, while a dining area with patio furniture is visible. The space is accessed through a glass sliding door from the interior.
Home in North York
5 out of 5 average rating, 13 reviews

Luxe, Family-Friendly Oasis Home With Pool

SergeRating, 5 stars3 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
The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.
Home in Scarborough
4.95 out of 5 average rating, 100 reviews

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

MelissaRating, 5 stars1 week ago
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.
Guest favorite
The exterior of a Victorian-style home is framed by lush greenery. The exposed brick facade is complemented by vertical vines climbing the walls. Windows with white trim are positioned symmetrically, allowing natural light to enhance the inviting appearance of the house.
Home in Niagara
4.91 out of 5 average rating, 299 reviews

King West Victorian Studio Gem

MRating, 5 stars4 days ago
One of the best Airbnb stays! I love the character of the space, the location is fantastic, and the availability of amenities all around. The best part was the softness of the bed sheets! I value a good night sleep, and the bed was so comfortable. Wi-Fi was extremely fast and made working from home a breeze. The kitchen is well stocked with everything needed to make yourself at home. Thank you Kathleen. I'll definitely book again in the future.

Condo rentals with a pool

Guest favorite
Condo in Downtown Toronto
4.88 out of 5 average rating, 122 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

KarenRating, 5 stars1 month 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 favorite
An indoor pool area is visible, featuring a large, rectangular pool surrounded by tiled flooring. Floor-to-ceiling windows allow natural light to fill the space. Lounge chairs are positioned along the edges, and a seating area can be seen in the background.
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
An outdoor pool area features a clear blue pool reflecting the evening sky. Sun loungers are placed along the edge of the pool, and modern lighting illuminates the space, highlighting the surrounding architecture.
Condo in Downtown Toronto
4.9 out of 5 average rating, 182 reviews

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

RogerRating, 5 stars3 weeks ago
Katherine was super helpful and clear. She gave helpful recommendations and was always prompt when responding to questions. Thanks so much!
Guest favorite
The indoor pool area features large windows that allow natural light to fill the space. The pool is beautifully tiled, with a shallow area marked for safety. Comfortable lounge areas are situated beside the pool, offering a relaxing atmosphere.
Condo in Fort York
4.89 out of 5 average rating, 414 reviews

Lakeside Condo Studio In Downtown Toronto

IeishaRating, 5 stars2 weeks ago
Very clean and great locations for nights in downtown Toronto
Guest favorite
A modern condo building features large glass windows and a striking red sculpture at the forefront. Landscaped greenery is visible along the pathway, enhancing the contemporary urban setting. The surrounding area includes a paved walkway and sleek, geometric architectural elements.
Condo in Downtown Toronto
4.92 out of 5 average rating, 88 reviews

Luxury Designer Condo, steps to CN tower

MarkRating, 5 stars6 days ago
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.
Guest favorite
A rooftop pool features crystal-clear water and is surrounded by modern buildings with expansive glass facades. Lounge chairs line the pool area, offering a space for relaxation with views of the city skyline.
Condo in Downtown Toronto
4.93 out of 5 average rating, 150 reviews

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

BhalchandraRating, 5 stars1 week ago
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.
Top guest favorite
Condo in Downtown Toronto
5 out of 5 average rating, 125 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

LauraRating, 5 stars4 days ago
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.
Guest favorite
The rooftop pool area is displayed, featuring a clear blue pool bordered by sleek stone tiles. Towering glass buildings create a modern backdrop, with the CN Tower visible nearby. Lush trees line the space, providing a touch of greenery against the urban landscape.
Condo in Downtown Toronto
4.92 out of 5 average rating, 73 reviews

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

RichardRating, 5 stars1 week ago
Alexander’s place is a nice Condo in a well kept, secure building a short distance from Billy Bishop airport and located in the middle of everything. It was easy walking to restaurants, Scotiabank Arena, Rogers Centre CN Tower, HHOF and plenty of pubs and clubs and restaurants. We were three brother-in-law‘s in town for a hockey game between the Leafs and the Habs and having a two bedroom condo located where this one is was absolutely perfect for our needs. The host Alexander was great, very responsive to any questions!

Quick stats about vacation 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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