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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 Downtown Toronto

4.91 out of 5 average rating, 127 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

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 favourite

Condo in Downtown Toronto

5 out of 5 average rating, 113 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

Enjoy our luxury 3 bedroom [2 queen 1 double bed], 2 bathroom condo, located in the heart of the Entertainment District. The condo is a short walk to many of the city’s most exciting attractions - CN Tower, Rogers Centre, Scotiabank arena, and the Metro Convention Centre. There is plenty of shopping, fine dining and entertainment in the surrounding areas accessible by foot. For our guests pleasure we have designed the condo to be modern, stylish, and relaxing. We looking forward to hosting you!

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.

Condo in Downtown Toronto

4.87 out of 5 average rating, 105 reviews

Luxury 1BR Executive Suite with Stunning Views!

This beautifully designed 1BR condo has it all: a spacious, open concept suite with high ceilings and hardwood floors throughout; beautifully designed; inviting living area with sofa, armchair and large flat screen TV; small dining table comfortably seats 3 guests; modern kitchen with stainless steel appliances, dedicated work space; bedroom with comfortable queen size bed, bathroom with shower/tub; washer/dryer ensuite. High speed Internet, absolutely stunning panoramic views of Toronto!

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

4.93 out of 5 average rating, 205 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 favourite

Condo in Downtown Toronto

4.95 out of 5 average rating, 137 reviews

High Floor | CN Tower, ScotiaArena, Rogers, MTCC

Entire stylish and modern condo in the heart of DT Toronto! WALK to Toronto's main attractions: → CN Tower / Aquarium / Rogers Centre (7 mins) → Scotiabank Arena (2 mins) → Union Station (2 mins) → Lake Ontario Waterfront (3 mins) → Direct access to the underground PATH Highlights: → Secured building access with 24/7 concierge → Spacious balcony with patio set → Electrical fireplace → Washer + dryer with detergent →MONTHLY STAYS: Access to fitness centre, pool, sauna!

Guest favourite

Condo in Downtown Toronto

4.94 out of 5 average rating, 155 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 Downtown Toronto

4.95 out of 5 average rating, 196 reviews

Upscale Luxurious Condo Free Parking

IN THE HEART OF IT ALL....CONDO IN THE CLOUDS The Space Come stay and enjoy the awesome VIEW from my private condo. Situated in the heart of it all....SCOTIA BANK CENTRE, ROGERS CENTRE, RIPLEY'S AQUARIUM, METRO TORONTO CONVENTION CENTRE, THE WATER FRONT, THE ENTERTAINMENT DISTRICT AND THE HOCKEY HALL OF FAME. Longo's Grocery Store, Starbucks, Bank(TD), Real Sports Bar, Eleven Restaurant, Sports Store and the Path System all located at the main floor of the condo.

Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 118 reviews

Vacation Getaway:Heated Pool-Hottub Open 365 Days

Welcome to the Toronto Beach and to this century old home, right on the beach with a private pool and spa that is 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 favourite

Condo in Downtown Toronto

4.97 out of 5 average rating, 235 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.

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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

4.97 out of 5 average rating, 34 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Guest favourite

Home in Scarborough

4.91 out of 5 average rating, 57 reviews

Ravine Paradise ! heated pool and hot tub!

Home in Oshawa

4.75 out of 5 average rating, 12 reviews

PS4 + BBQ: 5 Bedroom, 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

Guest favourite

Home in North York

4.92 out of 5 average rating, 50 reviews

Toronto Pool Retreat

Home in Ajax

4.83 out of 5 average rating, 12 reviews

Entire Modern Home | Spacious | Near Lake & Park

Home in Pickering

4.8 out of 5 average rating, 35 reviews

Toronto Vacation with Heated Pool/Park/Zoo/Casino

Condo rentals with a pool

Condo in Downtown Toronto

4.86 out of 5 average rating, 111 reviews

2 Bedroom CN Tower Waterfront Oasis w Parking

Guest favourite

Condo in Downtown Toronto

4.89 out of 5 average rating, 174 reviews

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

Condo in Downtown Toronto

4.87 out of 5 average rating, 318 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

Guest favourite

Condo in Downtown Toronto

5 out of 5 average rating, 25 reviews

Prime location • Amazing views • FREE parking spot

Guest favourite

Condo in Downtown Toronto

5 out of 5 average rating, 11 reviews

Lovely 1 BR Suite + Gym + Pool, MTCC, CN Tower

Guest favourite

Condo in Downtown Toronto

5 out of 5 average rating, 47 reviews

Luxury Downtown Condo For 6 (CN Tower View)

Guest favourite

Condo in Downtown Toronto

4.98 out of 5 average rating, 63 reviews

Modern 2BR 2BATH Urban Core Hotel-Style Condo

Guest favourite

Condo in Downtown Toronto

5 out of 5 average rating, 58 reviews

#1 on Airbnb | 3 BR | Free Parking | No Clean Fee

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