Vacation rentals with a pool in York

4.98 out of 5 average rating, 225 reviews

Stylish Downtown Toronto Condo + Free Parking

Experience downtown Toronto in a stylish condo! Start your day by enjoying coffee on the balcony. Walk to BMO Field (Toronto Stadium) - ideal for concerts, sports & FIFA events. Walk to Exhibition Place, CN Tower, Rogers Centre, Ripley’s Aquarium, restaurants & waterfront. Full kitchen, 2 desks with fast WIFI. Building features a pool, hot tub, sauna, gym, rooftop BBQ, free parking & self check-in. Discounts for 7+ nights & non-refundable bookings. Book your unforgettable Toronto stay today!

A light-filled bedroom features a spacious bed dressed in crisp white linens. Two bedside tables with lamps stand on either side. A large window provides a glimpse of the city outside, complemented by a decorative indoor plant and modern wall art.

4.97 out of 5 average rating, 193 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

Enjoy our luxury 3 bedroom [2 queen 1 double bed], 2 bathroom condo, located in the heart of the Entertainment District. The condo is a short walk to many of the city’s most exciting attractions - CN Tower, Rogers Centre, Scotiabank arena, & the Metro Convention Centre. There is plenty of shopping, fine dining and entertainment in the surrounding areas accessible by foot. For our guests pleasure we have designed the condo to be modern, stylish, and relaxing. We look forward to hosting you!

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.

4.99 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

4.98 out of 5 average rating, 168 reviews

Downtown Oasis w/ Sunset Lake Views & Parking

Lake and skyline out the window by day, and a sunset over the water that stops you mid-sentence by night. Bright, stylish, and right on the downtown Toronto waterfront with free underground parking, rare this close to the core. Steps to the waterfront trail, Coronation Park, and King West's restaurants and bars. Minutes from BMO Field, CN Tower, Rogers Centre, Scotiabank Arena, Budweiser Stage, Ripley's Aquarium, and Billy Bishop Airport. There's more here than fits in a description.

4.92 out of 5 average rating, 168 reviews

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.

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

25th-Floor Lake Views | Free Parking | Steps to BMO Field Experience Toronto from the clouds! This modern, whisper-quiet studio offers breathtaking, unobstructed lake views. Liberty Village, CNE, Rogers Center, Ripley's Aquarium, Enercare Centre and more all within 10 minutes walk. *Free heated underground parking *Gigabit Wi-Fi & 4K Roku TV *Full kitchen, gym, pool & sauna *Authorized legal rental, professionally cleaned, and ready for you. Book your stay!

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 !

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

4.99 out of 5 average rating, 160 reviews

The Fort York Flat

Welcome to the Fort York Flat! This 2 Bedroom, 1 Bathroom space has been thoughtfully renovated using a mixture of modern and contemporary decor to create a relaxing, upscale place to kick back while enjoying everything Downtown Toronto has to offer. Our location and smart lockbox located at the front doors makes checking into the flat easier than ever, no need to worry about fussing with the front desk staff or waiting for elevators.

4.97 out of 5 average rating, 122 reviews

The entrance features a wide stone staircase leading to double wooden doors with intricate designs. Potted plants add greenery on either side, while a pathway is lined with grass and nearby trees. The home's facade showcases classic stonework and a tiled roof.

Place to stay in Toronto

The Snug Oasis - Woodstock (Near Airport)

Make some memories at this enchanting, family-friendly ranch style estate. Welcomed by old Oak trees and classic stone facades, your suite is on the ground floor. A warm wooden chamber abundant in antique charm, it overlooks the gorgeous garden and resort size pool. Birds chirping, bunnies visiting; nearby restaurants and poolside barbecues make it the perfect retreat!

Popular amenities for York rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

4.91 out of 5 average rating, 348 reviews

Home in Niagara

King West Victorian Gem Downtown - Walk Everywhere

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

4.92 out of 5 average rating, 126 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

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

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

4.93 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

4.95 out of 5 average rating, 43 reviews

A modern living area features a cozy sectional sofa and two accent chairs in blue and green. A sleek coffee table sits at the center, and a fireplace is framed by a stylish mantel. Large windows allow natural light to brighten the space.

Home in East York

Leaside Rental w/ Backyard& Pool

Condo rentals with a 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 spacious living area features a brown leather sofa paired with a comfortable armchair. A large window allows natural light to fill the room, revealing views of the city skyline. A coffee table sits centrally, complemented by a stone fireplace and decorative elements.

4.94 out of 5 average rating, 106 reviews

Explore the City Centre from Condo with Views

A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.

4.95 out of 5 average rating, 163 reviews

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

4.98 out of 5 average rating, 105 reviews

A stylish living area features a leather sofa and an accent chair, creating a cozy seating arrangement. A modern coffee table is positioned centrally, with a small plant and decorative items. The open kitchen area includes sleek cabinetry and a microwave, enhancing the contemporary design.

Condo in Yorkville

Yorkville Luxury Suite | Pool, Sauna & Gym Toronto

A modern living area features a dark sofa with decorative cushions, positioned beside a glass-top dining table and a small plant. Natural light filters through large windows, illuminating the space, while a framed world map adds a touch of elegance to the wall.

4.93 out of 5 average rating, 228 reviews

Stylish 1BR/2 bed CN Tower view, Free Parking

A living area features two brown leather sofas positioned near large windows, offering a view of the downtown skyline. A floor lamp stands beside a decorative bench, and two floral paintings adorn the wall, adding a touch of elegance to the modern space.

4.96 out of 5 average rating, 102 reviews

Prime location • Amazing views • FREE parking

A light-colored sofa is positioned in the foreground, adorned with plush, textured pillows. The modern kitchen in the background features white cabinetry, stainless steel appliances, and a central island topped with decorative items, creating a fresh and inviting space.

4.86 out of 5 average rating, 162 reviews

Luxury Condo with lake view and Free 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

Other vacation rentals with a pool

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.

4.92 out of 5 average rating, 185 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

A dining table with a circular glass top and four black chairs is positioned near large windows, offering expansive views of the Toronto skyline. A small potted plant adds a touch of greenery, while natural light fills the space, enhancing the modern interior.

4.97 out of 5 average rating, 139 reviews

The Farmer's Cottage

5.0 out of 5 average rating, 12 reviews

Apartment in Toronto

1 Bedroom-King bed with parking steps to the lake

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

4.86 out of 5 average rating, 64 reviews

A modern bedroom features a spacious bed with crisp white linens and a contrasting dark headboard. Two bedside lamps emit a soft glow, and a decorative wall piece adds visual interest. A sleek nightstand is positioned on either side of the bed, enhancing the room's functionality.

Apartment in Toronto

Lakeview Luxury Condo Suite

Apartment in Liberty Village

The living area features a light-colored couch accompanied by two armchairs. A wooden coffee table sits centrally, adorned with decorative items. A desk with a chair is positioned in the background, and large windows allow natural light to brighten the space.

Lux Top-Floor w/ CN Tower Views

4.85 out of 5 average rating, 87 reviews

4.87 out of 5 average rating, 45 reviews

Apartment in Toronto

Stellar Humber Bay 2BD/2BTH Large Patio & Parking