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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Superhost

Home in McLaughlin

4.79 out of 5 average rating, 48 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

Welcome to our spacious 5 bedroom / 3 bathroom bungalow with 3 queen beds, 2 king beds, 2 kitchens, 2 dining areas, and 2 cozy living rooms. With 3 bathrooms and plenty of space, it's ideal for families or groups. Conveniently located near shopping, HWY 401, and just a 45-minute drive to Toronto. IMPORTANT: Pool not available in Mid Sept to May. Outdoor Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

Guest favourite

Guesthouse in Uxbridge

4.93 out of 5 average rating, 40 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Welcome to Redwood Haven, your lavish Uxbridge retreat! 2 bedrooms await, comfortably accommodating 4 guests. Be captivated by breathtaking views, immerse yourself in luxury, taking a dip in the inviting heated pool (shared by attached East and West units residents and guests). Embark on thrilling equestrian adventures for an extra touch of excitement. With ample parking, heating, and AC, ensuring the ultimate comfort throughout your stay. Unleash unforgettable memories in this enchanting haven.

Guest favourite

Home in Scarborough

4.95 out of 5 average rating, 118 reviews

Modern Custom Home w/ Pool, Games & Parking

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!

Guest favourite

Guest suite in Scarborough Village

4.89 out of 5 average rating, 103 reviews

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.

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 556 reviews

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.

Guest favourite

Bungalow in Whitby

4.88 out of 5 average rating, 16 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 opens in june until September For monthly discounts contact us

Guest favourite

Home in Hampton

5 out of 5 average rating, 10 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 Whitby

4.8 out of 5 average rating, 10 reviews

Luxe 4BR Retreat w/ Heated Pool, Hot Tub & BBQ

Welcome to your ultimate getaway – a beautifully maintained, spacious 4-bedroom, 2.5-bath family home designed for relaxation, entertainment, and comfort. Whether you're planning a weekend escape, a family vacation, or a longer stay near Toronto, this home has everything you need for a memorable experience. Step into your own backyard paradise! Enjoy a refreshing swim in the private heated pool, soak your cares away in the hot tub, or fire up the BBQ grill for a delicious outdoor meal.

Top Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 153 reviews

Heated Pool-tub Open 365 Days

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, 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

Guest favourite

Home in Port Perry

4.93 out of 5 average rating, 229 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

Guest suite in Uxbridge

4.78 out of 5 average rating, 18 reviews

Forest Retreat | Pool, BBQ & Fall Colors

Hilltop retreat on 22 acres with panoramic views, just 2 min from Lake Ridge Ski Resort. Perfect for a cozy fall escape. Features: 1 bedroom + living room (convertible to 2nd bedroom) Pool still open for refreshing swims BBQ for outdoor dining under the trees Direct access to Glen Major Forest hiking & biking trails Peaceful privacy with sunrise & sunset views Vibrant fall colors and crisp country air Ideal for couples, families & adventurers seeking both comfort and nature.

Guest favourite

Home in Uxbridge

4.85 out of 5 average rating, 95 reviews

The Ridge Roost - Uxbridge Township

Two floors of large two bedroom house (no access to walk out basement) located in beautiful Uxbridge Township, Canada's trail capital. Minutes by car from either skiing, golfing or hiking, this beautiful property is only an hour from Toronto and is the perfect escape from the city. 10-15 minutes by car to town, either Uxbridge or Port Perry, puts you in easy reach for grocery shopping when planning your meals.