
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.

Toronto's Perfect View Apartment
Beautiful apartment with a wonderful view! You will have an unobstructed observation of the Toronto's CN Tower, Yacht Club at the harbor, Toronto City Airport and lake Ontario. Fully equipped gym, swimming pool and roof top terrace. You will be minutes away from most city attractions as well as the Exhibition Place. Book now for an unforgettable stay! Please be sure to check my GuideBook for best selection of restaurants and local business discounts for my guests. Send your inquiry for any info!

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!

Modern Designer Home w/ Pool Open Game Rm/Fire Pit
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!

Prestigious Bluffs Private Guest Suite
Beautiful, private, sun-filled guest suite with a large private yard and pool in a safe, upscale, tranquil, forested neighbourhood. Deer and other wildlife. Short walk to public transport (TTC, GO Trains), shopping, restaurants, parks and trails to the top of the Bluffs with breathtaking views of Lake Ontario and also down to the waterfront trail to nearby Bluffers Park Beach and Marina. Parking for 6 vehicles and boat trailer. Fast Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

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.

Ask re: FALL Specials-Heated Pool-tub Open 365 Day
Ask about FALL BONUS NIGHTS: BOOK 2 nights-get 3rd for free: Located right by the lake. HEATED private pool and spa. OPEN 365 days- EVEN IN WINTER !! Explore local shops on Queens St. 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

Lux Waterfront Condo by Rogers -IndoorPool-Parking
This lakeside condo is designed to give you a 5-star experience. Upon entrance you are greeted with champagne and a gift basket! Steps away from the main attractions. Walk to the CN Tower, Scotia Bank Arena, Rogers Centre, Ontario Place, Cinesphere Theatre, Budweiser Stage, Historic Fort York, Billy Bishop Airport (YTZ), BMO Field, and more! Enjoy your 5-star stay with our amenities including an indoor pool, jacuzzi, sauna, odyssey gym (located on the same floor), outdoor roof top hot tub!

“Amazing 2 Bedrooms Condo” in Downtown Toronto”
Enjoy your luxury condo in heart of Entertainment District. Best location in the downtown! Very close to all major attractions but silence and comfortable to enjoy city life. Breathtaking view, step away from CN Tower, Aquarium, Metro Convention Centre, Rogers Centre, TiFF, Union Station, Scotiabank Arena, Lake Ontario and others Outdoor pool in 15th floor with CN Tower view (seasonally open), gym area with new equipments, hot tub, steam room and other amenities ready for your leisure

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.

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.

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.

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Modern Corner Unit with Stunning Views | 1+1 BR at 209 Fort York – Prime Downtown Location Step outside and you're just minutes from Toronto’s top attractions: 🗼 CN Tower & Ripley’s Aquarium ⚾ Rogers Centre & Scotiabank Arena 🎡 Exhibition Place & BMO Field 🌊 Harbourfront Centre & Toronto Islands Ferry 🌳 Coronation Park & Martin Goodman Trail 🛍️ Queen West & King West Everything downtown is easily accessible with steps away from public transportation.
Popular amenities for Whitby rentals with a pool
House rentals with a pool

Beautiful Cottage in Ajax

Backs onto nature near IBM and Hospital

Ravine Paradise ! heated pool and hot tub!

Private Home + PS4 + Foosball: 5 Bedrooms, 3 Baths

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Guest suite 10 min to subwy w kitchen FREE parking

Victorian Charm – TIFF/FIFA Base in King West

Casa Meya - Toronto Poolhouse Villa
Apartment rentals with a pool

Beautiful Skyline View Downtown Toronto

Luxury Condo with FreeParking. CN Tower Lake View

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

⭐️KING Bed Luxury Condo - CN Tower View + Parking⭐️

Luxury 1 Bedroom Suite In Heart Of Toronto

Charming Condo w Parking, CN Tower View & Pool

Spacious And Sun Filled, Modern

Studio by Lake -Close to Central Airport & Station
Other holiday rentals with a pool

Stylish Downtown Toronto Condo | Lakeside Living

Walk to CN Tower | 1+1 BR | Free Parking

The Farmer's Cottage

Private 2-Bdrm Hideaway with Parking

Stylish 1 BDRM/ GYM/WIFI/ Laundry

Toronto Pool Retreat

The Ridge Roost - Uxbridge Township

Penthouse Corner Suite w/ Panoramic 12 FT Windows
Quick stats about holiday rentals with a pool in Whitby
Total holiday rentals
Explore 30 holiday rentals in Whitby
Nightly prices starting at
Whitby holiday rentals start at € 17 per night before taxes and fees
Verified guest reviews
Over 370 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 of Whitby holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Whitby rentals
4.5 Average rating
Whitby stays receive an average rating of 4.5 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Toronto City Hall
- Jackson-Triggs Niagara Estate
- Christie Pits Park