
Holiday rentals with a pool in York
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in York
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Modern Private Suite By Subway w Free Parking
An entire floor is yours to use privately. Newly renovated with modern amenities, includes a 55" Smart OLED TV, Fibre Optic High-Speed WIFI, and backyard full of fun activities for couples and families. Next to public transit, a quick walk away, is TTC Eglinton W station. Centrally located, quick access to downtown or any neighbouring city (Vaughan, Markham, Brampton, Mississauga). Situated on a quiet street and walking distance from grocery stores, pharmacies, coffee shops, and eating places.

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.

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

Charming Condo w Parking, CN Tower View & Pool
Enjoy your stay at a charming & modern condo located in the heart of downtown Toronto. Stop settling for sub-par accommodations, and treat yourself to this fully equipped, meticulously cleaned unit with 1 Queen Bed + 1 Sofa Bed. You will be within steps (literally) to the CN Tower, Rogers Center, Ripley’s, and many of Toronto’s top attractions. I am an extremely passionate & attentive host who will cater to your requests and desires. Shoot me a message to get started on your Toronto getaway.

“Amazing 2 Bedrooms Condo” in Downtown Toronto”
Enjoy your luxury condo in heart of Entertainment District. Best location in the downtown! Very close to all major attractions but silence and comfortable to enjoy city life. Breathtaking view, step away from CN Tower, Aquarium, Metro Convention Centre, Rogers Centre, TiFF, Union Station, Scotiabank Arena, Lake Ontario and others Outdoor pool in 15th floor with CN Tower view (seasonally open), gym area with new equipments, hot tub, steam room and other amenities ready for your leisure

Corner Unit in Liberty Village (Parking + Balcony)
Free parking available+ Close proximity to Budweiser Stage. Located in Liberty Village - one of Toronto’s most sought-after neighborhoods - this corner unit is a place to live, work, & play. The spacious, 700 sq ft layout offers 270-degree views of the city and Lake Ontario. With floor-to-ceiling windows, this 1 Bedroom + Den is flooded with natural light and zero wasted space. Enjoy a morning coffee or watch the sunset over cocktails on either of the two walk-out balconies.

Resort Style Lake View Condo
Welcome, step into luxury! This bright & spacious open concept condo boasts gorgeous south facing views of Lake Ontario. Conveniently located in a quaint neighborhood where downtown Toronto is still only minutes away! Enjoy 5 star condo amenities such as pools, gym, studios, 24hr Concierge & More! Walking distance to shops, TTC, GO Train, Restaurants & so much more! Convenient commuter location with easy access to the 401/427 highways and the Gardiner expressway.

Year-Round Heated Pool & Hot Tub Family Oasis
Enjoy your own private, year-round heated pool and spa just steps from the lake. Kayaks, volleyball, tennis, and basketball gear are ready for you whenever adventure calls - and when winter arrives, lace up your skates or go for walks on the boardwalk ! Inside, a gourmet kitchen, wood-burning fireplace, and four inviting bedrooms offer a cozy retreat for your entire group. The pool and hot tub are heated to a comfortable 87–102°F, every single day of the year.

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.

Condo in Heart of Mississauga
Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym
We are back! A Luxury 2-bedroom overlooking the city. Open concept living space with a modern flare and stainless steel appliances, encompassing the city life. Bedrooms have comfy queen beds and loads of closet space. Stunning views of the CN Tower and lake. Parking, Pool, Spa, Sauna, and gym access.

Humber Bay Family Friendly condo w Terrace&Parking
Located in Toronto's west end, overlooking the lake with bike paths, kayaking and canoeing, beaches and boating at your doorstep. Classic decor with a large terrace/balcony for entertaining. Steps away from restaurants, bars, and shopping with groceries and LCBO across the street.
Popular amenities for York rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Cozy 2 bed Condo Near Scotiabank/Rogers/Union

Seraya Wellness Retreat

Luxury Spa Escape with Pool & Jacuzzi

Lake Ontario Waterfront House 15 Min To DT Toronto

private backyard SPA oasis in Toronto

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

Chic King West Studio – TIFF & FIFA at Your Door
Apartment rentals with a pool

Lux Spacious 3 Beds w CN Tower View (Free Parking)

Downtown Toronto Condo/Parking/ Sleeps 4/ Balcony

Luxury Condo with FreeParking. CN Tower Lake View

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

Beautiful Lake View Studio Condo + 1 free Parking

Large & Bright 2BR+Den in Midtown w/ Free Parking

Luxury Downtown Condo For 4 (CN Tower Views)

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Other holiday rentals with a pool

Vibrant City Stay: Patio, Gym, and Pool Access

Cityscape Oasis w/ Private Patio & Parking

The Farmer's Cottage

Luxury 2BR - Subway/Pool/Gym/Sauna + Free Parking

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

Amazing View in High-rise Condo

Downtown Designer Condo

1Bd+ Den Cozying Apartment in Midtown Toronto
When is the best time to visit York?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $116 SGD | $112 SGD | $111 SGD | $115 SGD | $124 SGD | $133 SGD | $131 SGD | $135 SGD | $130 SGD | $142 SGD | $120 SGD | $130 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals with a pool in York

Total holiday rentals
Explore 80 holiday rentals in York

Nightly prices starting at
York holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 1,290 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of York holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across York rentals

4.8 Average rating
York stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
York’s top spots include Christie Pits Park, Dufferin Grove Park and Dufferin Station
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Toronto City Hall
- Casino Niagara
- Rouge National Urban Park




