Holiday rentals with a pool in Vaughan

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

4.97 out of 5 average rating, 507 reviews

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

Fully renovated 2 bedroom walkout basement modern suite(1,100 sqft), increased in size windows, feels like ground floor, 20x30 swimming pool. 3 minutes to UTM. This home is in a quiet, peaceful neighborhood that offers access to scenic walks and parks nearby. 2 minutes to HWY. DWTN Toronto and DWTN Mississauga is close which makes dining at great restaurants, browsing boutique shops, shopping malls and general sightseeing both easy and convenient. Pool/seasonal/notHeated LICENSE# 2022-000188-STA

A comfortable living area is presented with a light-colored sectional sofa and a brown leather armchair. A modern entertainment unit displays a flat-screen television, complemented by framed artwork on the walls. A soft area rug partially covers the wooden floor, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 130 reviews

Luxury Downtown Condo For 4 (CN Tower Views)

Step into luxury at this stylish condo that sleeps 4 nestled in the vibrant Entertainment District. Immerse yourself in city life with proximity to iconic attractions such as the CN Tower, Metro Convention Centre, Rogers Centre, & Scotia Bank Arena—all just steps away. A short stroll leads you to an array of upscale dining, shopping, and entertainment options. Enjoy the modern and tranquil ambiance we've curated within the unit, while taking in the breathtaking CN Tower view from the balcony.

4.98 out of 5 average rating, 130 reviews

Luxury Downtown Condo For 6 (CN Tower View)

Luxury awaits in our sophisticated 2bed, 2bath condo in the Entertainment District. This prime location places you steps away from Toronto's CN Tower, Metro Convention Centre, Rogers Centre, Hockey Hall of Fame & Scotia Bank Arena. Within a short walk, explore plenty of top dining, shopping, and entertainment options. Our unit is meticulously designed for modernity, elegance, and a truly relaxing experience. Enjoy our updated balcony with seating arrangements & breathtaking CN Tower views.

4.92 out of 5 average rating, 198 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

4.99 out of 5 average rating, 169 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

4.89 out of 5 average rating, 116 reviews

4.9 out of 5 average rating, 170 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

Apartment in Downtown Toronto

Skyline Condo | Free Parking | Steps to CN Tower

Stay in the heart of downtown Toronto with FREE PRIVATE PARKING included. This modern one-bedroom condo is just steps from the CN Tower, Rogers Centre and waterfront. Enjoy beautiful skyline views, floor-to-ceiling windows and a private balcony. The unit features a comfortable queen bed, sofa bed, full kitchen, smart TV, high-speed Wi-Fi and in-suite washer and dryer. Perfect for couples or small groups. Guests also have access to the building's gym and outdoor pool.

4.92 out of 5 average rating, 168 reviews

4.99 out of 5 average rating, 187 reviews

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

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

4.86 out of 5 average rating, 111 reviews

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

4.91 out of 5 average rating, 107 reviews

A swimming pool is featured in a serene outdoor space, surrounded by lush greenery and tall trees. The circular pool is complemented by a stone wall background. A shaded seating area with a table and chairs is nearby, promoting relaxation and enjoyment.

Home in Don Mills

Casa Meya – Toronto Poolhouse Villa

Casa Meya : This exclusive modern and fully renovated Villa at 2024. Upper Floor : Beautiful Kitchen with brand new Bosch and LG appliances. An Island to host 4 guests plus a 6 seats Dining Table. 85" Samsung QLED TV to watch included Premium TV channels. Master Bedroom ( KING ) - 65" TV / 1st Bathroom 2nd Bedroom ( QUEEN ) - 42" TV / 2nd Bathroom Lower Floor : 3rd Bedroom ( QUEEN ) - 42" TV / 3rd Bathroom

Popular amenities for Vaughan rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 349 reviews

Home in Niagara

King West Victorian Gem Downtown - Walk Everywhere

4.76 out of 5 average rating, 119 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

4.82 out of 5 average rating, 11 reviews

Home in Brampton

Heated Pool Estate by Canterra Stays · Sleeps 20

4.95 out of 5 average rating, 19 reviews

Home in Don Mills

Luxury 4BR Designer Retreat with Heated Wave Pool

4.96 out of 5 average rating, 25 reviews

Home in Cheltenham

Indoor Pool & Hot Tub Villa | Sleeps 14

4.93 out of 5 average rating, 75 reviews

A charming exterior of a spacious home is showcased, featuring a blend of stone and wood accents. Neatly trimmed hedges line a stone pathway that leads to the entrance. The well-maintained landscaping is complemented by a driveway and a garage.

Home in Scarborough

Private Pool Lakeview House

5.0 out of 5 average rating, 7 reviews

Home in Thornhill

Tranquil Estate Retreat | Pool, Pond on 3 Acres

4.93 out of 5 average rating, 74 reviews

A modern luxury home is displayed with a contemporary stone facade and wooden accents. The upper balcony features a glass railing, and a well-kept lawn enhances the inviting exterior. The driveway leads to a double garage with stylish doors.

Home in North Etobicoke

Beautiful Oasis In the city with Heated Pool

Condo rentals with a pool

4.82 out of 5 average rating, 123 reviews

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

Condo in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

4.98 out of 5 average rating, 168 reviews

Downtown Oasis w/ Sunset Lake Views & Parking

A rooftop pool reflects the blue sky while providing views of the CN Tower and surrounding modern buildings. Lounge chairs are positioned beside the pool, creating a relaxed atmosphere. The clear water invites enjoyment against the urban backdrop.

4.94 out of 5 average rating, 180 reviews

Rooftop Pool Condo with CN Tower View

4.98 out of 5 average rating, 225 reviews

Stylish Downtown Toronto Condo + Free Parking

A balcony view captures the iconic CN Tower alongside a modern building structure. The expansive glass windows reflect the urban skyline and lake in the distance, evoking a sense of openness and connection to the city.

4.85 out of 5 average rating, 206 reviews

Toronto CN Tower 2 Bed 2 B w Master King w Parking

A modern living area features a grey sectional sofa paired with a wooden coffee table. Natural light streams through large windows, revealing a view of the city. A 55-inch Smart TV is positioned on a dark wood console, complemented by decorative elements on the table.

4.94 out of 5 average rating, 151 reviews

Charming Condo w Parking, CN Tower View & Pool

The image captures a vibrant urban landscape featuring a modern building with glass and metal elements. The prominent CN Tower stands in the background against a clear blue sky. The area is filled with pedestrians enjoying the surroundings, complemented by greenery and architectural structures.

4.85 out of 5 average rating, 106 reviews

Central downtown condo next2 CNtower+free parking

A desk with an ergonomic chair is positioned near floor-to-ceiling windows, offering a stunning view of Lake Ontario at sunset. The scene features a vibrant sky with hues of orange and purple, along with glimpses of the surrounding greenery and cityscape.

4.98 out of 5 average rating, 111 reviews

Fort York- Lake View Studio Condo + Indoor Parking

Other holiday rentals with a pool

Guest suite in Scarborough

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

New Custom-Built | Marble Pool + BBQ | Toronto

4.91 out of 5 average rating, 149 reviews

5.0 out of 5 average rating, 46 reviews

The spacious bedroom is designed with light neutral tones, featuring a large bed with layered bedding. Soft warm lighting is provided by a stylish chandelier. A comfortable seating area with modern chairs and a decorative table complements the room, along with a large window surrounded by elegant drapes.

Apartment in King City

The King's Rest

Condo in Mimico-Queensway

A bright living area features a soft sofa and a low coffee table, with a large TV mounted on the wall. Floor-to-ceiling windows provide expansive views of the cityscape, while natural light illuminates the space. A transition to the sleeping area is visible in the background.

Stunning Toronto view! Guest Favourite w/ parking!

4.9 out of 5 average rating, 83 reviews

5.0 out of 5 average rating, 4 reviews

Condo in Mississauga

Sunset Retreat | 2BR/2BA | CN Tower View + Parking

Apartment in Richmond Hill

A spacious living area features a modern sofa contrasting with warm wood flooring. Large glass doors invite natural light and provide access to a balcony, while a low table displays decorative items. A serene view of the outdoors complements the bright atmosphere.

Entire 2 BDR Suite - Good Location

4.97 out of 5 average rating, 36 reviews

4.9 out of 5 average rating, 83 reviews

Guest suite in Markham

Hidden Gem of Thornhill (Ravine+Pool+Hot tub)

5.0 out of 5 average rating, 12 reviews

Apartment in Toronto

1 Bedroom-King bed with parking steps to the lake