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Holiday 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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Condo in North York

4.8 out of 5 average rating, 325 reviews

Spacious Downtown (midtown) 2bed 2 bath free parki

In the heart of Midtown (close to downtown), this is a modern 2 Bedroom, 2 Bathroom, 900 square foot loft, in a high rise building. My place is perfect for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets) are welcome too! The condo is in pristine condition with a fully equipped kitchen, living area, two comfy beds, two full piece washrooms and a balcony with all the luxuries and amenities you need. My spot is close to Underground Subway Train Station - Yellow Line, 24/7 Bus Accessible, Yonge Street, 24 hour restaurants, 24 hour grocery store, Bars, Clubs, Restaurants, Movies, Highway 401. There is no shortage of things to do around here. Thank you for considering staying with me during your visit to Toronto. Whether you're coming for business, pleasure, or to visit family, I think you will tremendously enjoy my suite and my neighborhood.

Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 121 reviews

Heated Pool-Hottub Open 365 Days+Mid Week Specials

** Ask about MID WEEK Specials. 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 (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Condo in Downtown Toronto

4.92 out of 5 average rating, 130 reviews

Modern 2 Bd condo near CN tower/MTCC/Rogers Centre

This spacious and modern suite is conveniently located in the heart of Toronto (Front and John Street). It’s situated within the Entertainment District, home to Toronto’s iconic CN Tower (3-5 min walk), Ripley’s Aquarium, Rogers Centre and the Metro Toronto Convention Center (directly across the street). Amenities: Parking Available for Charge Free unlimited high-speed WiFi Smart TVs w/ cable, Youtube & Netflix Fully equipped kitchen Private balcony Rooftop Infinity Pool Gym access & hot tub

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 553 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.

Guest favourite

Farm stay in Kawartha Lakes

4.88 out of 5 average rating, 121 reviews

Luxury, One-of-a-kind Pool and Zen with Horses

Luxury spaces for the whole family, YEAR ROUND Zen with horses in our heated barn, magnificent views. Private suite, Fire Pit, Covered patio, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball, badminton, bocce ball. Something for everyone! Book an archery tag or axe throwing game! Search horse experiences Sky Haven Equestrian in Bethany. Kids Stay Free! When booking enter number of adults only. Wutai Shan Bhuddist Garden is 4 min. away.

Villa in North York

4.94 out of 5 average rating, 134 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.

Guest favourite

Condo in Davisville Village

4.93 out of 5 average rating, 252 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

Guest favourite

Home in Port Perry

4.93 out of 5 average rating, 213 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.

Guest favourite

Condo in Downtown Toronto

4.94 out of 5 average rating, 158 reviews

Stylish 1BR/2 bed CN Tower view, Free Parking

Centrally located, The Rogers Centre, MTCC and CN Tower are right across the street! Walking distance to Financial District, Union Station, bars, Scotia Bank Arena, with easy access to the 401 & more! The space has 10 foot ceilings and windows, with a south view of the CN Tower. Parking space included! This unit is on the quiet LOFT side of building. Other listings may seem similar, but if it’s on the tower side, it’s much busier and elevators may have longer waits.

Guest favourite

Condo in Fort York

4.98 out of 5 average rating, 109 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.

Guest favourite

Condo in Downtown Toronto

4.98 out of 5 average rating, 117 reviews

Trendy King West townhome

Lovely 1-bdrm townhome in King West area, one of the most trendy, lively and vibrant neighbourhoods, offers some of the best restaurants in Toronto. It is close enough to the action of downtown Toronto, but still have that community feel of a SoHo-like neighbourhood. This 1-bdrm apartment is perfect for a couple or a single business traveler. Conveniently located on the ground floor with a cozy and quiet backyard.

Guest favourite

Guest suite in Uxbridge

4.96 out of 5 average rating, 188 reviews

Mackenzie Cottage

Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane

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Popular amenities for Whitby rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Ajax

4.91 out of 5 average rating, 35 reviews

Beautiful Cottage in Ajax

Guest favourite

Home in Scarborough

4.92 out of 5 average rating, 60 reviews

Ravine Paradise ! heated pool and hot tub!

Home in Oshawa

4.71 out of 5 average rating, 14 reviews

[30%+OFF] PS4 + BBQ: 5 Br, 3 Bath - 2 Units in 1!

Guest favourite

Home in Uxbridge

5 out of 5 average rating, 29 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Home in Ajax

4.83 out of 5 average rating, 12 reviews

Entire Modern Home | Spacious | Near Lake & Park

Guest favourite

Home in Scarborough

4.93 out of 5 average rating, 112 reviews

Entire house with Pool, ravine, and nature trail

Home in Pickering

4.81 out of 5 average rating, 36 reviews

Toronto Vacation with Heated Pool/Park/Zoo/Casino

Guest favourite

Home in Niagara

4.91 out of 5 average rating, 293 reviews

King West Victorian Studio Gem

Condo rentals with a pool

Guest favourite

Condo in Fort York

4.94 out of 5 average rating, 126 reviews

One Of A Kind Downtown Sanctuary w/ CN Tower View

Guest favourite

Condo in Fort York

4.96 out of 5 average rating, 126 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

Guest favourite

Condo in Downtown Toronto

4.89 out of 5 average rating, 175 reviews

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

Guest favourite

Condo in Fort York

4.97 out of 5 average rating, 109 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

Guest favourite

Condo in Downtown Toronto

4.89 out of 5 average rating, 823 reviews

1 Bedroom Suite - Downtown Core (near MTCC/Rogers)

Guest favourite

Condo in Downtown Toronto

4.95 out of 5 average rating, 197 reviews

Upscale Luxurious Condo Free Parking

Guest favourite

Condo in Fort York

4.98 out of 5 average rating, 180 reviews

Stylish Downtown Condo with Free Parking

Guest favourite

Condo in Downtown Toronto

4.9 out of 5 average rating, 287 reviews

Closest condo to Rogers Centre/CN tower in Toronto

Quick stats about holiday 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
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool

Destinations to explore