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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Guest favorite

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.

Guest favorite

Condo in Downtown Toronto

4.99 out of 5 average rating, 139 reviews

Bright Modern Central 2Bd2Ba Lakeview + Big Screen

Welcome to The Perch — our beloved pied-à-terre in the most vibrant city, Toronto. Comfort and design define this bright, creative, cozy, curated, and clean space. Enjoy our perch above it all! We have chosen everything within these walls based on how it makes us feel. The floors feel good on bare feet. The mattresses and pillows inspire sleep. Sheets and towels are luxuriously soft. The lighting is an ode to mood. Made with love, shared with love. See more @ ThePerchToronto on socials

Guest favorite

Home in Scarborough

4.93 out of 5 average rating, 112 reviews

Entire house with Pool, ravine, and nature trail

Enjoy your stay in this artsy, minimalistic 2 story home. The entire house is yours! This house has 3 bedrooms, each with a queen bed, night stand, closet space, and USB charging ports. One room has a desk/workspace. It also has 2 full bathrooms, open concept kitchen/living/dining rooms, and laundry and one parking spot on the driveway. We offer high speed WIFI, and a wall mounted, 55" flat screen, 4K, Roku Smart TV. In addition, we have a Keurig machine with complimentary coffee and tea.

Guest favorite

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 favorite

Rental unit in Downtown Toronto

4.94 out of 5 average rating, 126 reviews

5-Star Condo beside CN Tower

Mere steps to Toronto’s most popular attractions including the CN Tower, Ripley’s Aquarium, Rogers Centre, Roy Thomson Hall and the Metro Toronto Convention Centre. Located in the entertainment district at the heart of the city with a wide selection of the finest dining, shopping, night life and entertainment. Amenities including an infinity outdoor rooftop swimming pool and fitness center. Enjoy 5 star welcome from concierge. Great for families, solo adventurers and business travelers!

Superhost

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 favorite

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 favorite

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 favorite

Condo in Downtown Toronto

4.93 out of 5 average rating, 209 reviews

College Park :2Bd+2bth + Free parking

950 sq.ft. luxurious 2 Bed 2 Bath including underground parking. In the coveted Bay and College neighbourhood. 5-10min walk to University, Queens Park, Dundas Square,Eaton Centre, Yorkville,ROM, City Hall,Nathan Philips SquareChurch Street, UofT, Ryerson 20-25 minute walk to CN Tower;Rogers Center 3 Min : Womens Hospital, 7 mins to Toronto General Hos Loblaws, 24 hr Metro Walking Distance to 3 subway stations (Wellesley,Queens Park,College Station). Pool,Gym,Hot Tub

Guest favorite

Condo in Downtown Toronto

4.93 out of 5 average rating, 141 reviews

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

Welcome to SohoTO! This stylish 920ft² / 85.5m² condo in DT Toronto. Enjoy stunning views from the rooftop pool, stay active in the well-equipped gym, and just steps away from MTCC and the CN Tower with secure parking included! ☞Please Note that the Outdoor Rooftop Pool is only open from June to Mid October every year ☞Highspeed Gigabit Fibe 3.0 internet/WiFi ☞Across the Street from the Metro Convention Centre ☞Peloton ☞Light Weights and Yoga Matt ☞Vinyl Player

Superhost

Condo in Downtown Toronto

4.88 out of 5 average rating, 305 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

Guest favorite

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