
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.

Luxury Downtown 2Bed by ScotiaBank Arena + Parking
Welcome to Maple Leafs Square! This stunning 2-bed, 2-bath corner suite offers free parking & breathtaking views of the city, CN Tower & Lake Ontario. Enjoy direct access to essential amenities like a supermarket, liquor store, Starbucks, restaurants, bars & banks. Perfectly located just steps from Union Station, Scotiabank Arena & a short 5-min walk to the CN Tower, Lake & Harbourfront. Convenient access to Billy Bishop Airport & the UP Express from Pearson Airport. Ideal for exploring Toronto!

Modern Custom Built Walkout to Marble Pool Game RM
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!

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

Prestigious Bluffs Private Guest Suite
Enjoy this beautiful, private, sun-filled suite with a large secluded yard and pool in a safe, upscale and serene forested neighborhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles and an EV charger (Tesla/J1772).

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.

2 BHK home 5 min from Go Train
7 min walk from Whitby train and Lake, this is a 2 BR house that offers accommodation with a 2 private parkings The self contained apartment is located in a brightly lit lower floor features, a separate entrance, a living room, and a fully equipped kitchen & laundry room. Guests can enjoy sun bathing in the garden or a barbque grill with your family. The backyard is shared however the guests have a private entrance. The pool is opens in june until September For monthly discounts contact us

MillionDollarView49thFloor☀CN Tower LAKE W/Parking
Welcome to my 3-bedroom + Den(can be considered a small bedroom with curtains) on 49th floor condo conveniently located close to CN Tower, Roger Center, lakeshore, Entertainment and Financial District (5-10 min walking). Scotiabank Arena, Supermarket, LCBO are basically across the street! → Approx. 1232ft² / 111m² of space → Free secure parking for 1 vehicle → Walk score of 100! → Transit score of 100! ( Union Go Train and subway station) → In-unit washer + dryer → Fully equipped kitchen

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.

Fireplace High-Floor w/ Balcony, Near CN Tower
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!

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub
Unwind in style at our year-round heated pool & soothing hot tub—the heart of this luxury 4-bed family oasis. Inside you’ll find plush beds, smart TVs, speedy Wi-Fi and a fully stocked chef’s kitchen. Outside, enjoy the fenced backyard with BBQ, lounge seating and night lighting. Pool & hot tub open 365 days Baby gear: crib, high-chair, safety gates Games galore: board games, books & playroom Seconds to beaches, shops and dining—yet peaceful enough for stargazing.

Canadiana Downtown Condo w/King Bed + Free Parking
We pride ourselves on delivering a 5 star hotel-like experience!! Condo offers FREE PARKING inside of the building. Whether you're in town for a concert, sporting event, business trip or just to catch some local touristic hotspots, you'll be within 8min walk of your destination. Condo is attached to Scotiabank Arena + Union. The condo has a King Bed and 2 Queens to comfortably accomodate your large group. Book now there's a surprise waiting inside!

Private Walkout Suite | 3 PM Checkout | 1.5G Wifi
Travel on your own terms with early check-in and a rare 3 PM late checkout. Located at the Finch/Dixie junction, this 600sqft executive suite offers 1.5G Fiber, a King Bed, and a private walkout for the discerning modern traveler. Relax by the fireplace, utilize the equipped office desk, and enjoy a full kitchen with total indoor privacy. (Laundry and the landscaped yard with a seasonal pool access are shared spaces)
Popular amenities for Whitby rentals with a pool
House rentals with a pool

Walk-out Luxury basement with Gym & Theatre

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Ravine Paradise ! heated pool and hot tub!

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

Luxe, Family-Friendly Oasis Home With Outdoor Pool

The Ridge Roost - Uxbridge Township

Casa Meya – Toronto Poolhouse Villa

Private Pool Lakeview House
Condo rentals with a pool

Cozy, Modern & Spacious Condo In Downtown Toronto!

Modern Designer Suite w/ Lake & City Skyline Views

Exceptional DT 2Bedrm+2Bath High floor w/ Pool!

Luxury Designer Condo | Downtown Toronto Retreat

Amazing View in High-rise Condo

Boutique 1BR | Parking•Walk to Subway | Gym•Sauna

Chic Downtown Hideaway 2B Condo

Chic Downtown Condo w/ Private Patio + Parking
Other holiday rentals with a pool

Classic 1BR+Den Apartment in Downtown. Gym, Pool

Wellesley Station 3-Min, Museums & Winter Shopping

Waterfront community ideally for long stays

Stylish 1BR on Toronto’s Harbourfront

Mackenzie Cottage

Royal 1B Condo in Downtown T.O.

Urban Gem, 3 Mins to Wellesley Station, Balcony

Downtown Toronto 2 BDR Condo CN Tower/Lake Views
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 $28 AUD per night before taxes and fees

Verified guest reviews
Over 410 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Whitby holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Whitby rentals
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Pet-friendly rentals Whitby
- Waterfront rentals Whitby
- Cottage rentals Whitby
- House rentals Whitby
- Fitness-friendly rentals Whitby
- Townhouse rentals Whitby
- Family-friendly rentals Whitby
- Rentals with a patio Whitby
- Rentals with a fire pit Whitby
- Apartment rentals Whitby
- Private suite rentals Whitby
- Rentals with lake access Whitby
- Rentals with a washing machine and dryer Whitby
- Rentals with a fireplace Whitby
- Rentals with outdoor seating Whitby
- Rentals with an EV charger Whitby
- Rentals with breakfast Whitby
- Rentals with beach access Whitby
- Rentals with a hot tub Whitby
- Rentals with pools Durham
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- Distillery District
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Downsview Park
- Toronto City Hall
- Christie Pits Park




