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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Guest favourite

Flat

4.95 out of 5 average rating, 20 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Guest favourite

Home

4.99 out of 5 average rating, 123 reviews

Christmas Specials Heated Pool-tub Open 365 Days

** 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 favourite

Apartment

4.99 out of 5 average rating, 142 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 favourite

Guest suite

4.89 out of 5 average rating, 92 reviews

Comfortable Suite in the Prestigious Bluffs Area

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.

Guest favourite

Flat

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

Home

4.92 out of 5 average rating, 13 reviews

Lakeview Cottage in the City with Pool

Cottage in the City with gorgeous Lake Ontario view, specious land for 50 people with pool within a safe city area. A cottage in the city is a rare and delightful find, a tranquil oasis amidst the hustle and bustle of urban life. Cottage in the City is located 5 minutes away from the Beaches Area where you can find delicious ice cream, multiple restaurants, and local stores and 20 minutes away from downtown Toronto, CN Tower, and the Distillery district. Parking for 4 cars is available.

Guest favourite

Home

4.93 out of 5 average rating, 215 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

Apartment

4.93 out of 5 average rating, 211 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

Home

4.91 out of 5 average rating, 11 reviews

A Quite 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 closed from September 2024 this year

Guest favourite

Apartment

4.93 out of 5 average rating, 145 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

Home

4.82 out of 5 average rating, 39 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

Guest favourite

Home

4.93 out of 5 average rating, 54 reviews

Toronto Pool Retreat

Experience prestige and privacy in our spacious, well-maintained family home. Enjoy resort-like living with a private yard featuring an inviting pool, hot tub, and large deck. Plus, indulge in additional entertainment options like air hockey and ping pong. Perfect for entertaining! Steps away from ravines, parks, and nature trails, plus easy access to amenities and transportation. Your ideal Toronto getaway awaits!