Vacation 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

Apartment in Downtown Toronto

4.98 out of 5 average rating, 44 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

Top guest favourite

Home in The Beaches

4.99 out of 5 average rating, 140 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.

Top guest favourite

Condo in Fort York

4.98 out of 5 average rating, 186 reviews

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!

Guest favourite

Guest suite in Scarborough

4.89 out of 5 average rating, 94 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

Apartment in Downtown Toronto

4.94 out of 5 average rating, 18 reviews

Stylish Condo with Patio + Gym, Rooftop Pool!

*GREAT LOCATION + SUPERHOST!* Welcome to your Private Condo in the Heart of Toronto, steps from the Rogers Centre, CN Tower, Convention Centre, Scotiabank Arena & more! Our building offers unmatched amenities; gym, hot tub, & rooftop pool with CN Tower View! The condo itself is bright and spacious with a large private patio. It has a Queen bed in the bedroom, a sofabed in the living room, fully-equipped kitchen/dining area, desk space, full bathroom, and ensuite laundry for you to enjoy!

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

Home in Hampton

5 out of 5 average rating, 7 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

4.94 out of 5 average rating, 16 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.

Superhost

Bungalow in Whitby

4.87 out of 5 average rating, 15 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 until June 2025 For monthly discounts contact us

Guest favourite

Home in Port Perry

4.93 out of 5 average rating, 218 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

Home in Pickering

4.85 out of 5 average rating, 46 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 in North York

4.91 out of 5 average rating, 68 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!