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 favorite

Home in Scarborough

4.97 out of 5 average rating, 34 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Surrounded By Nature,This East-End Toronto Gem Features A Heated 4Ft Deep Pool(Open May-Oct),Pergola w/Ample Seating+BBQ On An Over-Sized Deck.The HGTV Inspired Renos Will Make Your Stay Extra Special.A True Get-Away Where Lasting Memories Will Be Made! ✔ 5-7 Min to PanAM Centre, Toronto Zoo, Rouge Beach &Train Station ✔ 10 Min To Pickering Casino ✔ 35 Min to CNtower ✔ 35 Min To YYZ airport ✔ 5 Min Walk to TTC bus stop ✔ 5 Min To Groceries ✔ 5 Min To Highland Creek Village ✔ 10 Min To The Guild

Guest favorite

Guest suite in Scarborough

4.89 out of 5 average rating, 91 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 both 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. Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

Guest favorite

Home in Scarborough

4.93 out of 5 average rating, 112 reviews

Entire house with Pool, ravine, and nature trail

Enjoy your stay in this artsy, minimalistic 2 story home. The entire house is yours! This house has 3 bedrooms, each with a queen bed, night stand, closet space, and USB charging ports. One room has a desk/workspace. It also has 2 full bathrooms, open concept kitchen/living/dining rooms, and laundry and one parking spot on the driveway. We offer high speed WIFI, and a wall mounted, 55" flat screen, 4K, Roku Smart TV. In addition, we have a Keurig machine with complimentary coffee and tea.

Guest favorite

Guesthouse in Pickering

4.91 out of 5 average rating, 90 reviews

Cozy Cabin w/ Private Hot tub & Firepit

Cozy cabin w/ fully private hot tub, propane bbq and Firepit. Relax and unwind at this unique and tranquil getaway. Enjoy a private soak in the hot tub, then cozy up to the fire (wood provided) all while enjoying gorgeous views and open skies. Just minutes from the conveniences of the city yet completely surrounded by nature. Mini fridge, coffee/hot chocolate, indoor/outdoor games, books, dishes/utensils are also provided. Washroom is off-grid behind the cabin fyi. Pool and shower seasonal only

Guest favorite

Treehouse in Port Perry

4.98 out of 5 average rating, 553 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 favorite

Condo in Downtown Toronto

4.93 out of 5 average rating, 69 reviews

Luxury Downtown Condo Welcomes You - Free Parking

Stunning, centrally located 1 bdrm PLUS den in Downtown, Toronto. Steps away from the Village, Yorkville, Yonge Street, metro and close to Ryerson, U of T, Eaton Centre, Financial District and more. Very large private balcony looking South lake view with stunning West views. 1 bdrm with Queen size bed plus office. Ensuite laundry. 24 hr grocery store downstairs. 55” TV w/ Netflix and high-speed internet. Outdoor pool* (see notes), large 24 hr gym, and bbq and lounge area.

Guest favorite

Guest suite in Scarborough

4.95 out of 5 average rating, 91 reviews

New Cstm Bld-Extrmly Cozy Htd flrs+Fire Pit+GameRm

Welcome to our brand new, luxury modern unit located in a quiet, family-friendly neighbourhood only minutes from HWY 401, TTC & countless amenities! Newly and lovingly curated space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer / dryer and free parking. This upscale oasis is truly the perfect space for business travellers, young professionals and couples alike!

Guest favorite

Home in Port Perry

4.93 out of 5 average rating, 213 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 favorite

Home in The Beaches

4.99 out of 5 average rating, 118 reviews

Vacation Getaway:Heated Pool-Hottub Open 365 Days

Welcome to the Toronto Beach and to this century old home, right on the beach with a private pool and spa that is 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.

Superhost

Home in Pickering

4.8 out of 5 average rating, 35 reviews

Toronto Vacation with Heated Pool/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 favorite

Home in North York

4.92 out of 5 average rating, 50 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!

Guest favorite

Guest suite in Uxbridge

4.96 out of 5 average rating, 185 reviews

Mackenzie Cottage

Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane