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Vacation 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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A panoramic balcony view reveals the iconic CN Tower alongside city skyline reflections on a modern glass building. Red outdoor seating provides a contemporary touch, surrounded by a spacious tile floor that invites relaxation amidst the urban landscape.

Condo in Downtown Toronto

4.87 out of 5 average rating, 134 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

Welcome to Maple Leafs Square! This stunning 2-bed, 2-bath corner suite offers free parking & breathtaking views of the city, CN Tower & Lake Ontario. Enjoy direct access to essential amenities like a supermarket, liquor store, Starbucks, restaurants, bars & banks. Perfectly located just steps from Union Station, Scotiabank Arena & a short 5-min walk to the CN Tower, Lake & Harbourfront. Convenient access to Billy Bishop Airport & the UP Express from Pearson Airport. Ideal for exploring Toronto!

Top guest favorite

A chic living area features a gray chaise sofa adorned with pastel pillows, complemented by light pink curtains. A marble-top dining table sits near a flat-screen TV mounted on the wall, while a decorative bowl adds a touch of elegance to the coffee table.

Condo in Fort York

4.98 out of 5 average rating, 200 reviews

Stylish Downtown Toronto Condo with Free Parking

Experience downtown Toronto in a stylish condo! Start your day in a bright kitchen & enjoy coffee on the balcony. Relax with Netflix after exploring the city. Walk to CN Tower, Rogers Centre, Ripley’s Aquarium, Exhibition Place, restaurants & waterfront. Full kitchen, Keurig, 2 desks for work. Building features pool, hot tub, sauna, gym, seasonal rooftop BBQ, free parking & self check-in. Discounts on stays of 7+ nights & non-refundable bookings. Book your unforgettable Toronto getaway today!

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

4.96 out of 5 average rating, 112 reviews

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

A bright bedroom showcases a spacious bed with white linens and a textured blanket. A yellow accent pillow adds color. A bedside lamp and a framed artwork are positioned thoughtfully, while large windows provide panoramic views of the city.

Condo in Downtown Toronto

4.88 out of 5 average rating, 124 reviews

Luxury 1BR Executive Condo • Panoramic City Views

★ This stylishly appointed 1BR condo has everything you need: a spacious open-concept layout with high ceilings and hardwood floors throughout; warm, modern décor; a cozy living area with sofa, armchair, and large flat-screen TV; dining table that seats 3; sleek kitchen with stainless steel appliances; dedicated workspace; comfortable queen bed in the bedroom; bathroom with shower/tub combo; in-suite washer/dryer; high-speed internet; breathtaking panoramic views of Toronto; and an A+ location!

A serene pond is visible, with a person kayaking on calm waters. A wooden dock is in the foreground, featuring two white lounge chairs and a blue float. Lush greenery surrounds the pond, complementing the tranquil atmosphere.

Treehouse in Port Perry

4.98 out of 5 average rating, 555 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in North York

4.94 out of 5 average rating, 160 reviews

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

The garden area features a fenced backyard with a pool surrounded by lounge chairs and umbrellas. Colorful flowers and greenery add to the landscape. Visible are shaded seating areas, inviting for relaxation and enjoyment.

Bungalow in Whitby

4.88 out of 5 average rating, 16 reviews

2 BHK home 5 min from Go Train

7 min walk from Whitby train and Lake, this is a 2 BR house that offers accommodation with a 2 private parkings The self contained apartment is located in a brightly lit lower floor features, a separate entrance, a living room, and a fully equipped kitchen & laundry room. Guests can enjoy sun bathing in the garden or a barbque grill with your family. The backyard is shared however the guests have a private entrance. The pool is closed until June 2025 For monthly discounts contact us

Top guest favorite

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

4.99 out of 5 average rating, 151 reviews

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.

Home in Port Perry

4.93 out of 5 average rating, 226 reviews

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

An indoor swimming pool area is featured, with clear water inviting relaxation. A stainless steel handrail provides stability for entry, while large windows allow natural light to illuminate the space. The area is equipped with tiled flooring and a clock on the wall for convenience.

Condo in Davisville Village

4.85 out of 5 average rating, 111 reviews

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

1，Welcome to my home in the heart of midtown Toronto in the Yonge & Eglinton area! It sleeps three guests comfortably and is an excellent base for your Toronto adventures! 2，With excellent access to public transportation, you can be in downtown within 15 minutes; you are a 5-minute walk from Eglinton Subway Station, 2 mins from TTC, and within walking distance to tons of shops and restaurants. 3，Loblaws (grocery) & LCBO (liquor) on the main floor of the building.

Top guest favorite

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

Apartment in Fort York

4.99 out of 5 average rating, 114 reviews

The Fort York Flat

Welcome to the Fort York Flat! This 2 Bedroom, 1 Bathroom space has been thoughtfully renovated using a mixture of modern and contemporary decor to create a relaxing, upscale place to kick back while enjoying everything Downtown Toronto has to offer. Our location and smart lockbox located at the front doors makes checking into the flat easier than ever, no need to worry about fussing with the front desk staff or waiting for elevators.

Top guest favorite

An indoor pool area is illuminated by natural light streaming through large floor-to-ceiling windows. The pool features a shallow section marked clearly, with lounge seating visible nearby for relaxation. Fresh greenery can be seen outside, enhancing the tranquil environment.

Condo in Fort York

4.98 out of 5 average rating, 133 reviews

Artsy and Comfy Home with a View

This 670 sqft, 1 Bed+Den, 1 Bath has 9 foot ceilings and a spacious layout, plus: ▶︎ Free underground parking ▶︎ Streetcar direct to Union Stn, Bathurst Stn, Spadina St ▶︎ Restaurant-cafe downstairs, grocery store within 100m ~ 5-min walk: Loblaws, Starbucks, LCBO, Stackt Market, Farm Boy, BBT ~ 15-min walk: King St dining/nightlife, Queen St shopping... Rogers Center, Budweiser Stage, Canadian National Exhibition (CNE)... and more.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Whitby rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living room features comfortable seating arrangements, including a large sectional sofa and plush armchairs. A stone fireplace serves as a focal point, accompanied by a mounted artwork depicting a horse. A large television is positioned across from the seating area.

Home in Port Perry

5 out of 5 average rating, 10 reviews

Horse Farm Luxury Estate

Home in North York

5 out of 5 average rating, 20 reviews

Award Winning Luxury Home with Heated Pool + Sauna

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, 59 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

4.9 out of 5 average rating, 80 reviews

Ravine Paradise ! heated pool and hot tub!

An outdoor swimming pool occupies the center of a spacious backyard, surrounded by neatly arranged seating. Lush trees and greenery provide natural shade, while a wooden bench sits near the poolside, creating a serene environment for relaxation.

4.78 out of 5 average rating, 41 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

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, 19 reviews

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Home in North York

4.84 out of 5 average rating, 80 reviews

Toronto Pool Retreat

An open-concept living area features hardwood floors and exposed brick walls. A spacious bed is complemented by elegant chandeliers, while a white futon is situated nearby. Decorative artwork adorns the walls, and a light-filled kitchen area is visible in the background.

Home in Niagara

4.91 out of 5 average rating, 311 reviews

King West Studio Gem – Walk to TIFF & FIFA Fun!

Condo rentals with a pool

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, 140 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

A bright living area features a modern orange sectional sofa and a wooden coffee table. Large windows offer views of the cityscape. A dining area with high chairs is positioned beside a compact kitchen, with red cabinetry adding a pop of color.

Condo in Downtown Toronto

4.9 out of 5 average rating, 107 reviews

Beautiful Condo Across CN Tower and MTCC

A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.

Condo in Fort York

4.98 out of 5 average rating, 122 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

A light-colored sofa is positioned in the foreground, adorned with plush, textured pillows. The modern kitchen in the background features white cabinetry, stainless steel appliances, and a central island topped with decorative items, creating a fresh and inviting space.

Condo in Fort York

4.86 out of 5 average rating, 125 reviews

Luxury Condo with FreeParking. CN Tower Lake View

A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.

Condo in Downtown Toronto

4.97 out of 5 average rating, 250 reviews

Chic, High-Rise Apartment with CN Tower Views

A comfortable living area features a sofa adorned with decorative cushions and two accent chairs. A cozy area rug with geometric patterns lies beneath, while a dining bar with seating for four is visible in the open-concept kitchen, complemented by stainless steel appliances.

Condo in Davisville Village

4.93 out of 5 average rating, 163 reviews

Large & Bright 2BR+Den in Midtown w/ Free Parking

The outdoor pool is surrounded by lounge chairs, inviting relaxation. Soft lighting accentuates the area, creating a serene atmosphere as evening approaches. Modern structures and seating arrangements are visible in the background, enhancing the space's appeal.

Condo in Downtown Toronto

4.92 out of 5 average rating, 290 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

A modern high-rise condominium building is visible, featuring a sleek façade of glass and metal. The surroundings include various city structures and signage, with a mix of urban architecture and a cloudy sky above.

Condo in Downtown Toronto

4.93 out of 5 average rating, 142 reviews

Luxurious heart of downtown condo next to CN Tower

Other vacation rentals with a pool

A modern living space features a light-colored sofa adorned with vibrant cushions. A stylish coffee table sits on a geometric rug, alongside a sleek TV console. Large windows provide natural light, with greenery visible through the glass, complementing the minimalist kitchen layout.

Apartment in Downtown Toronto

4.89 out of 5 average rating, 45 reviews

Urban Luxury in the Heart of Downtown Toronto

Two blue Adirondack chairs are positioned facing a large swimming pool under a clear blue sky. The pool area is equipped with slides and features shaded sections nearby, inviting relaxation and enjoyment.

Camper/RV in Haydon

4.74 out of 5 average rating, 47 reviews

The Happy Camper @ Cedar Park Resort

Top guest favorite

A rooftop pool is showcased, featuring a smooth, clear blue surface reflecting the CN Tower. The surrounding glass walls highlight the urban skyline, while the sun bathes the area in natural light, creating a serene environment for relaxation.

Condo in Downtown Toronto

5 out of 5 average rating, 72 reviews

Vine & View Suite - 300 Front St W

A rooftop pool area is showcased with a clear blue pool bordered by tiled edges. White lounge chairs are positioned nearby, and covered cabanas line the perimeter. Sky and city views are visible in the background, enhancing the open atmosphere.

Loft in Downtown Toronto

4.9 out of 5 average rating, 79 reviews

Modern Downtown Loft with Private Garden

A sunlit living area features modern furniture, including a tufted beige sofa and a pink accent chair. A round coffee table sits atop a circular rug, while large windows provide a view of the outdoors. Artwork adorns the wall, adding a touch of color.

Apartment in North York

4.78 out of 5 average rating, 9 reviews

Hallmark Luxury 1 BDR condo sbwy

An open-concept living area is displayed with a dining table and four chairs, a sleek kitchen with modern appliances, and a comfortable sofa. Floor-to-ceiling windows offer natural light and a view of the skyline. A small balcony with two chairs is visible.

Apartment in Downtown Toronto

4.85 out of 5 average rating, 20 reviews

Modern 2BR/2BA Condo | Heart of Downtown–Luxe Stay

The living room features a spacious, L-shaped sectional sofa surrounded by natural light from large windows. A wooden side table holds a decorative bowl. A plush area rug with a subtle pattern complements the warm tone of the wood floor.

Townhouse in Scarborough

4.8 out of 5 average rating, 41 reviews

Private 2-Bdrm Hideaway with Parking

Top guest favorite

Condo in Davisville Village

5 out of 5 average rating, 23 reviews

Modern 1-Bedroom in Midtown TO - 4 min Eglinton ST

Quick stats about vacation rentals with a pool in Whitby

Total rentals
30 properties
Total number of reviews
350 reviews
Family-friendly rentals
20 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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