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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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Guest favourite
A panoramic balcony view reveals the iconic CN Tower alongside city skyline reflections on a modern glass building. Red outdoor seating provides a contemporary touch, surrounded by a spacious tile floor that invites relaxation amidst the urban landscape.
Condo in Harbourfront
4.88 out of 5 average rating, 143 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

Welcome to Maple Leafs Square! This stunning 2-bed, 2-bath corner suite offers free parking & breathtaking views of the city, CN Tower & Lake Ontario. Enjoy direct access to essential amenities like a supermarket, liquor store, Starbucks, restaurants, bars & banks. Perfectly located just steps from Union Station, Scotiabank Arena & a short 5-min walk to the CN Tower, Lake & Harbourfront. Convenient access to Billy Bishop Airport & the UP Express from Pearson Airport. Ideal for exploring Toronto!

Superhost
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
4.94 out of 5 average rating, 124 reviews

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!

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, 181 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 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).

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, 557 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
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, 17 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

Superhost
Condo in Entertainment District
4.81 out of 5 average rating, 289 reviews

MillionDollarView49thFloor☀CN Tower LAKE W/Parking

Welcome to my 3-bedroom + Den(can be considered a small bedroom with curtains) on 49th floor condo conveniently located close to CN Tower, Roger Center, lakeshore, Entertainment and Financial District (5-10 min walking). Scotiabank Arena, Supermarket, LCBO are basically across the street! → Approx. 1232ft² / 111m² of space → Free secure parking for 1 vehicle → Walk score of 100! → Transit score of 100! ( Union Go Train and subway station) → In-unit washer + dryer → Fully equipped kitchen

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, 234 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, 182 reviews

Fireplace High-Floor 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 serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in The Beaches
4.99 out of 5 average rating, 170 reviews

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.

Top Guest favourite
A round marble dining table is featured in the center, surrounded by wooden chairs. Above hangs a stylish light fixture. A decorative hockey-themed wall art is displayed, reflecting local culture. The open kitchen area includes modern appliances and a neutral color scheme, enhancing the inviting space.
Apartment in Harbourfront
4.92 out of 5 average rating, 146 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

We pride ourselves on delivering a 5 star hotel-like experience!! Condo offers FREE PARKING inside of the building. Whether you're in town for a concert, sporting event, business trip or just to catch some local touristic hotspots, you'll be within 8min walk of your destination. Condo is attached to Scotiabank Arena + Union. The condo has a King Bed and 2 Queens to comfortably accomodate your large group. Book now there's a surprise waiting inside!

Superhost
Guest suite in Pickering
5 out of 5 average rating, 3 reviews

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)

Popular amenities for Whitby rentals with a pool

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 $28 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Whitby holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Whitby rentals

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