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

Condo in Fort York

4.98 out of 5 average rating, 182 reviews

Stylish Downtown Condo with Free Parking

Prep breakfast in a beaming kitchen with granite counters and head out onto a balcony to dine in the fresh air coming off the lake. Recharge on a chaise sofa in a chic living area boasting pastel colours, marble accents, and an electric fireplace. The perfect central location, by the lake & within walking distance to most coveted attractions, shopping, restaurants, coffee shops, clubs & bars. Take a stroll along the waterfront, or walk to the CN Tower, Rogers Centre, Exhibition Place, Fort York, Ripley's Aquarium, Ontario Place & lots more (see the neighbourhood tab below for a larger list) Toronto is an amazing city - we want you to feel at home in our condo, and have an unforgettable trip! Indoor Swimming Pool & Hot Tub Sauna Fitness Centre & Yoga Studio (with free wifi) Rooftop Terrace with BBQ's & Hot Tub (seasonal) Free-Parking (available upon request) Self Check-In with Smart Lockbox Full Service Kitchen with Coffee Maker & Kettle Two Desks For Work Wifi Netflix & Cable TV For flexible arrival times, keys will be accessible by a self check-in smart-lockbox. We are also available by text or phone if you have any questions! Set in a Downtown high-rise, the apartment is steps away from vibrant restaurants, upscale fashion boutiques, and buzzy nightlife spots. Popular attractions like the CN Tower, Rogers Centre, and the waterfront are a short walk away. Visit tourist attractions in Toronto by walking, bike rental, taking an uber/taxi or getting on the TTC (public transit) right outside the condo building. ♡ Chat with Victoria on Instagram @victoria.simpson

Guest favourite

Apartment in Downtown Toronto

4.97 out of 5 average rating, 33 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 in The Beaches

4.99 out of 5 average rating, 130 reviews

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

Condo in Fort York

4.97 out of 5 average rating, 112 reviews

Luxury Waterfront Downtown Condo w/ Pool & 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 hot tub and roof top!

Guest favourite

Villa in North York

5 out of 5 average rating, 11 reviews

Award Winning Designed Home with Sauna + Pool

Winner of the 2023 RESA Home Staging Industry Award, my house was professionally designed to ensure my guests have a 5-star atmosphere to enjoy their stay. It has 3 bedrooms with 4 beds total, as well as 3.5 bathrooms and a sauna. It is fully equipped with everything you'll need including comfortable Fairmont Royal beds , High Speed WiFi, several 4K TV's, spacious rooms and a large backyard in a ravine lot. It has been recently renovated and has a brand new deck to relax on by the pool.

Guest favourite

Apartment 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, 141 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 favourite

Home in Hampton

5 out of 5 average rating, 6 reviews

Enniskillen Vacation Home Retreat!

Located in a sought after community, this attractive modern home is situated on 3/4 acre surrounded by farmland and estate homes. Explore the area with tons to do! Conveniently 5min from 407, an hour east of Toronto, 10min from Canadian Tire Motorsport Park, 5min from Cedar Park (waterpark) 20min to Brimacombe Ski Hill & Ganaraska Forest, with many ATV, snowmobile, mountain biking and walking trails close. “Pack your bags and get ready for a memorable, stress-free stay at our retreat”

Superhost

Home in Scarborough

4.93 out of 5 average rating, 14 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 in Port Perry

4.94 out of 5 average rating, 216 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.

Superhost

Bungalow in Whitby

4.86 out of 5 average rating, 14 reviews

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 closed from September 2024 this year

Superhost

Home in Pickering

4.84 out of 5 average rating, 43 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.