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
A heated pool is set within a spacious patio area, featuring inviting blue waters and a bright green inflatable float. Two chairs are positioned alongside the pool, with a tall red umbrella providing shade. Lush greenery and a secure fence surround the area.
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
A modern kitchen area is presented with sleek white cabinetry and black appliances, complemented by a textured backsplash. A dining table with two black chairs sits invitingly, while greenery is introduced by a potted plant in the corner, enhancing the clean and contemporary design.
Home in Scarborough
4.95 out of 5 average rating, 122 reviews

Cozy Modern Suite•Heated Flrs•Game Rm•Free Pkg

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!

Top guest favourite
Soft shadows cast by the morning light create a beautiful pattern on the wall of the living area. A gallery-style arrangement of framed art is displayed, complemented by a modern sofa and decorative elements nearby.
Condo in Courtice
4.99 out of 5 average rating, 178 reviews

Bright Modern Central 2Bd2Ba Lakeview + Big Screen

Welcome to The Perch — our beloved pied-à-terre in the most vibrant city, Toronto. Comfort and design define this bright, creative, cozy, curated, and clean space. Enjoy our perch above it all! We have chosen everything within these walls based on how it makes us feel. The floors feel good on bare feet. The mattresses and pillows inspire sleep. Sheets and towels are luxuriously soft. The lighting is an ode to mood. Made with love, shared with love. See more @ ThePerchToronto on socials

Guest favourite
A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.
Guest suite in Scarborough Village
4.9 out of 5 average rating, 105 reviews

Prestigious Bluffs Private Guest Suite

Enjoy a beautiful, private, sun-filled guest 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 and down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles and an EV charger (Tesla/J1772).

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
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.

Superhost
A modern living space is highlighted by large windows that provide expansive views of the skyline and water. A comfortable seating area includes a gray sofa, while a dining table with transparent chairs is situated nearby. Decorative potted plants add a touch of greenery.
Condo in Courtice
4.83 out of 5 average rating, 125 reviews

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

Stunning 2 bedroom & 2 bath condo in the heart of downtown Toronto! Breathtaking views of the CN Tower, Lake, and southwest sunset. Steps away from the CN Tower, Scotiabank Arena, Rogers Centre, Union Station (airport express train direct), Convention Centre, Waterfront, and more. FREE PARKING for one vehicle. Luxurious amenities: rooftop pool, indoor pool, hot tubs, sauna, gym, theater room, party rooms. Grocery, Starbucks, restaurants, banks, bars inside the building on the ground floor.

Superhost
An outdoor seating area is presented with a glass-top table surrounded by four red cushioned chairs. A large red umbrella provides shade, while a grill is positioned nearby. The space is bordered by trees, creating a private and relaxed atmosphere.
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

Top guest favourite
A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.
Home in Port Perry
4.94 out of 5 average rating, 232 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 favourite
A modern living area showcases a large flat-screen TV mounted above a stylish media unit. An electric fireplace adds warmth to the space, while a bedroom area is visible in the background, featuring a neatly made bed with decorative pillows.
Condo in Harbourfront
4.93 out of 5 average rating, 178 reviews

Modern High-Floor Luxury w/ Balcony, Near CN Tower

Entire stylish and modern condo in the heart of DT Toronto! WALK to Toronto's main attractions: → CN Tower / Aquarium / Rogers Centre (7 mins) → Scotiabank Arena (2 mins) → Union Station (2 mins) → Lake Ontario Waterfront (3 mins) → Direct access to the underground PATH Highlights: → Secured building access with 24/7 concierge → Spacious balcony with patio set → Electrical fireplace → Washer + dryer with detergent →MONTHLY STAYS: Access to fitness centre, pool, sauna!

Top guest favourite
The interior features rustic log walls complemented by wooden beams. A dining area is set with a white tablecloth and dark chairs, while a vintage dresser holds decorative items. A minimalist wall art piece depicting a deer adds character to the warm space.
Guest suite in Uxbridge
4.95 out of 5 average rating, 231 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

Guest favourite
The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.
Condo in Unionville
4.91 out of 5 average rating, 123 reviews

Downtown Markham Unionville

Newer Condo, 2 bedroom entire unit, fully furnished with everything you need as if you were at home; steps to Historic Unionville, Cineplex with VIP Cinema,, Famous Ruth's Steak House, Good Catch Creole Seafood Place; Japanese Restaurant, Go-for-Tea Fusion, Historic Rouge Valley, Great Dining, Pubs, theatre, shopping Malls

Superhost
Apartment in Pickering
4.93 out of 5 average rating, 30 reviews

Airbnb King & Queen/Wifi/ near Toronto & Casino

Indulge in a stay that’s equal parts style and convenience. This beautifully furnished condo is located next to a bustling mall and countless restaurants. Shop, dine, and explore by day, then retreat to your modern condo oasis by night.

Popular amenities for Whitby rentals with a pool

Quick stats about vacation rentals with a pool in Whitby

  • Total vacation rentals

    Explore 30 vacation rentals in Whitby

  • Nightly prices starting at

    Whitby vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Whitby vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Whitby rentals

  • 4.5 Average rating

    Whitby stays receive an average rating of 4.5 out of 5 from guests

Destinations to explore

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