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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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Condo in Toronto

4.82 out of 5 average rating, 303 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.

May 9 – 16

ﺩ.ﺇ689 per night

Treehouse in Port Perry

4.98 out of 5 average rating, 533 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.

Jan 19 – 26

ﺩ.ﺇ1,403 per night

Villa in Toronto

4.94 out of 5 average rating, 116 reviews

➊ The One Toronto Villa - Indoor Pool&Tennis Court

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.

Jan 27 – Feb 3

ﺩ.ﺇ3,882 per night

Condo in Toronto

4.93 out of 5 average rating, 230 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.

Jan 1 – 8

ﺩ.ﺇ789 per night

Condo in Toronto

4.88 out of 5 average rating, 161 reviews

1Bedrm Condo|❤️ of Dt-Union Stn, Scotiabank Arena

Ideal location! Across the street from Union Station and Scotiabank Arena. Steps away from Toronto Convention Centre, CN Tower, Rogers Centre, Harbourfront, Ripley's Aquarium, and more. In the building you'll be staying in is a sports bar and grill, LCBO liquor store, large grocery store (also serving hot food), Starbucks, and a fine dining restaurant. Pay at the gate parking garage available in the building at a rate of $36 per 24 hours. Parking always available, no need to reserve.

May 11 – 18

ﺩ.ﺇ651 per night

Home in Port Perry

4.94 out of 5 average rating, 203 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.

Oct 18 – 25

ﺩ.ﺇ710 per night

Home in Toronto

4.91 out of 5 average rating, 265 reviews

King West Victorian Studio Gem

Victorian Century Home Quiet Residential Street in the Heart of Downtown Toronto Overlooks Park + Outdoor Public Pool Open Concept 735 sq ft Sunny, Exposed Brick, Chandeliers Hardwood Floors Throughout Soaring 11' Ceilings Fully Equipped Eat-in Kitchen Private Laundry Private Backyard/Garden Business Traveler Ready Steps to King Streetcar Minutes to Queen & King West Nightlife, Shops, Cafes + Restaurants & King West Theatre District Street Permit Parking

Jul 25 – Aug 1

ﺩ.ﺇ628 per night

Condo in Toronto

4.94 out of 5 average rating, 230 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

This Chic, Upscale Suite Is A Luxurious Home Base In The Heart Of Toronto's Entertainment District. The Perfect Location If Attending The Toronto International Film Festival (TIFF), And Just Steps To Nearby Venues, such as CN Tower, Rogers Centre, Subways, Restaurants, Shopping, Metro Toronto Convention Centre And Lake Ontario. Everything You Will Need To Have An Amazing Stay Is Included In The Unit. Perfect For Long Or Short Term Stays!

May 24 – 31

ﺩ.ﺇ851 per night

Apartment in Newmarket

5.0 out of 5 average rating, 141 reviews

The Hilton BnB Adult Luxury Suite

A beautifully decorated open concept walkout suite in an elegant 2-story home with all the amenities, accommodates 1-2 adult guests, in Newmarket’s prestigious Stonehaven Estates. The Hilton BnB is located just 30 minutes from downtown Toronto. Dine by the warmth of a fireplace in the winter or relax and have a BBQ poolside in the summer. The suite is spacious and the grounds are breathtaking. Uniquely designed with luxury in mind!

Nov 2 – 9

ﺩ.ﺇ412 per night

Condo in Toronto

4.97 out of 5 average rating, 218 reviews

Chic, High-Rise Apartment with CN Tower Views

Stay in our cozy and convenient downtown apartment for easy access to exciting activities and attractions. Enjoy our stylish living area, fully-equipped kitchen, and plush queen-size bed. Whether for business or leisure, our apartment is the perfect homely retreat to unwind and relax after a long day. Come experience a home-away-from-home feeling as you explore the diversity and culture of our beautiful city.

Aug 8 – 15

ﺩ.ﺇ1,220 per night

Apartment in Toronto

4.92 out of 5 average rating, 110 reviews

CN Tower View! Heart of Downtown

Entire Home is yours! You will not be sharing this listing Brand new, professionally decorated condo in the heart of downtown Toronto and financial district. Floor to ceiling windows! Enjoy being steps away to everything Toronto has to offer including Entertainment District, Financial District, Rogers Centre, Ripley's Aquarium, and all tourist attractions! Professionally cleaned after every single guest!

May 27 – Jun 3

ﺩ.ﺇ919 per night

Condo in Toronto

4.89 out of 5 average rating, 273 reviews

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE

This beautiful modern 1 bed & q bath suite is located in the heart of downtown Toronto's Entertainment & Financial District - in the prestigious 300 Front Street building in the core of the city. Enjoy a nice dinner on the balcony with a lake and CN Tower view! The building has a fully equiped Fitness center, Outdoor Pool with a 360 degree of the whole city, Steamroom, Whirlpool BBQ

Oct 19 – 26

ﺩ.ﺇ1,617 per night

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Whitby rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Whitby

4.87 out of 5 average rating, 31 reviews

Clean, spacious, poolside entire lower level apt

Oct 29 – Nov 5

ﺩ.ﺇ268 per night

Home in Ajax

5.0 out of 5 average rating, 9 reviews

Entire Modern Home | Spacious | Near Lake & Park

May 6 – 13

ﺩ.ﺇ868 per night

Home in Uxbridge

5.0 out of 5 average rating, 15 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Nov 30 – Dec 7

ﺩ.ﺇ857 per night

Home in Gormley

4.95 out of 5 average rating, 38 reviews

Lovely Home, Big Backyard + Pool

Mar 28 – Apr 4

ﺩ.ﺇ588 per night

Home in Pickering

4.93 out of 5 average rating, 14 reviews

Toronto Vacation with Heated Pool/Park/Zoo/Casino

Jul 21 – 28

ﺩ.ﺇ1,096 per night

Home in Ajax

4.88 out of 5 average rating, 24 reviews

Beautiful Cottage in Ajax

Oct 6 – 13

ﺩ.ﺇ3,153 per night

Home in Newmarket

4.82 out of 5 average rating, 17 reviews

Cozy Pool house in Newmarket

Sep 25 – Oct 2

ﺩ.ﺇ780 per night

Home in Toronto

4.91 out of 5 average rating, 33 reviews

Ravine Paradise with heated pool & hot tub!

Mar 20 – 27

ﺩ.ﺇ1,039 per night

Condo rentals with a pool

Condo in Toronto

4.84 out of 5 average rating, 121 reviews

Modern 1 Bdrm Suite Downtown District - Lake View

May 11 – 16

ﺩ.ﺇ716 per night

Condo in Toronto

4.95 out of 5 average rating, 171 reviews

Upscale Luxurious Condo Free Parking

Jan 18 – 25

ﺩ.ﺇ767 per night

Condo in Toronto

4.88 out of 5 average rating, 129 reviews

1 bdrm Condo by CNT Free Parking 39 FLR Stun. View

Sep 12 – 19

ﺩ.ﺇ890 per night

Condo in Toronto

4.86 out of 5 average rating, 178 reviews

Best View in Downtown 5 Star Luxury 1+1 w/office

May 14 – 19

ﺩ.ﺇ759 per night

Condo in Toronto

4.96 out of 5 average rating, 110 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

Nov 26 – Dec 3

ﺩ.ﺇ987 per night

Condo in Toronto

4.98 out of 5 average rating, 162 reviews

Stylish Downtown Condo with Free Parking

Jul 5 – 12

ﺩ.ﺇ1,002 per night

Condo in Toronto

4.95 out of 5 average rating, 113 reviews

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

Jul 15 – 22

ﺩ.ﺇ2,505 per night

Condo in Toronto

4.93 out of 5 average rating, 189 reviews

College Park :2Bd+2bth + Free parking

Nov 3 – 10

ﺩ.ﺇ1,097 per night

Quick stats about vacation rentals with a pool in Whitby

Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
220 reviews

Destinations to explore