
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.

Private Home + PS4 + Foosball: 5 Bedrooms, 3 Baths
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.

Modern Custom Built Walkout to Marble Pool Game RM
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!

Private Bluffs Suite | Pool | Pet-Friendly, Trails
Enjoy this beautiful, private, sun-filled suite with a large secluded yard and pool in a safe, upscale and serene forested neighborhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles and an EV charger (Tesla/J1772).

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.

Cedar Escape • Sauna • 10-Acre Private Forest
(Lic. STR2024-0005) Welcome to your private 10-acre forest estate, an exclusive sanctuary where refined luxury meets pristine nature. Wander serene woodland trails, refresh beneath the open-air forest shower, and gather fireside under a canopy of stars. Indulge in the soothing sauna, unwind poolside in complete privacy, and embrace the rare stillness surrounding you. Just minutes from the city, yet utterly secluded—offering elevated comfort, tranquility, and seamless high-speed connectivity.

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

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.

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub
Unwind in style at our year-round heated pool & soothing hot tub—the heart of this luxury 4-bed family oasis. Inside you’ll find plush beds, smart TVs, speedy Wi-Fi and a fully stocked chef’s kitchen. Outside, enjoy the fenced backyard with BBQ, lounge seating and night lighting. Pool & hot tub open 365 days Baby gear: crib, high-chair, safety gates Games galore: board games, books & playroom Seconds to beaches, shops and dining—yet peaceful enough for stargazing.

Private Walkout Suite | 3 PM Checkout | 1.5G Wifi
Travel on your own terms with early check-in and a rare 3 PM late checkout. Located at the Finch/Dixie junction, this 600sqft executive suite offers 1.5G Fiber, a King Bed, and a private walkout for the discerning modern traveler. Relax by the fireplace, utilize the equipped office desk, and enjoy a full kitchen with total indoor privacy. (Laundry and the landscaped yard with a seasonal pool access are shared spaces)

Pool/ King Bed/Wifi/Toronto LakeView/Free Parking
The Shopping & Dining Retreat Shop, dine, and relax in style. This chic 1-bedroom condo features high-end décor, a queen pull-out sofa, and a full kitchen. 🛍️ Just steps from a vibrant mall and countless restaurants. 🚆 Toronto is only 23 minutes away via GO. Perfect for weekend getaways, foodie trips, or retail therapy. Secure your dates now and enjoy the ultimate mix of comfort and city convenience!

2 Bedroom Modern Basement Apartment
In addition to the heated pool (currently closed for winter season), hot-tub (open year-round), and barbecue grill, your family will be close to everything you need to enjoy your stay at this centrally-located place. Places like Cedar Park resort, Port Darlington East Beach park, Freshco, banks, Shoppers Drugmart, hospital, Home Depot, Dollarama amongst others are just few mins away.

Private Pool Lakeview House
Enjoy a memorable visit when you stay in this unique place. Absolutely stunning waterfront cozy home near the Toronto bluffs beach. This is a gorgeous place in a classy neighbourhood with everything you need. Private pool and spacious yard with extraordinary views. Walking distance to the beach, Go transit, restaurants, grocery, pharmacy and more. You'll love it!
Popular amenities for Whitby rentals with a pool
House rentals with a pool

Horse Farm Luxury Estate

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Toronto Pool Retreat

Welcome to Gather House - Luxury Courtice Stay

The Ridge Roost - Uxbridge Township

Entire Modern Home | Spacious | Near Lake & Park

Family vacation home with Heated Pool-Toronto

Casa Meya – Toronto Poolhouse Villa
Apartment rentals with a pool

2 Beds 2 Bath Condo in Markham

“Modern 3BR Condo w/ Free Parking | 1 Min to 401”

Unionville Allure Suite

Cozy, Modern & Spacious Condo In Downtown Toronto!

Queen's Landing Markham Unionville

Lower Penthouse Suite with Pools & Sunset Views

Relax and stay in comfort

New Luxury Condo*Pano Views*Club Amenities*Park
Other holiday rentals with a pool

Toronto Yellow Comfy Entire Apartment

Relaxing stay with BBQ.

Modern home away from home in Courtice

The Princess Suite: Cozy Condo in Old Town Toronto

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Paris Flat Architect Designed Patio Bar Pool View

Lakeview Cottage in the City with Pool

Downtown Luxury Condo | Gym | Parking
Quick stats about holiday rentals with a pool in Whitby

Total holiday rentals
Explore 30 holiday rentals in Whitby

Nightly prices starting at
Whitby holiday rentals start at € 17 per night before taxes and fees

Verified guest reviews
Over 410 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Whitby holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Whitby rentals
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- BMO Field
- Distillery District
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Downsview Park
- Dufferin Grove Park
- Lakeridge Ski Resort
- York University
- Toronto City Hall
- Christie Pits Park




