
Vacation rentals with a pool in York
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in York

Total vacation rentals
Explore 90 vacation rentals in York

Nightly prices starting at
York vacation rentals start at G$4,176 GYD per night before taxes and fees

Verified guest reviews
Over 1,130 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of York vacation rentals include wi-fi 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
Top-rated rentals with a pool in York
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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!

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.

Luxury CN Tower & Lake Views Penthouse Sleeps 10
Experience luxury in our 41st-floor penthouse at 300 Front St W, Toronto. Steps from the CN Tower, this 2 Bedroom + Large Den (3rd Bedroom) offers stunning CITY, LAKE & SUNSET VIEWS. This beautiful apartment features a wrap-around balcony, 5 beds including a king bed, queen sofa bed, and a fully stocked kitchen. Enjoy CN Tower views from every bedroom, 100% Egyptian cotton linens & 4K Ultra HD TVs. Starbucks, a gym and an outdoor rooftop pool with exceptional views. Perfect for up to 10 guests.

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

Stunning Skyline View Condo, Steps to CN Tower
Stay in the heart of downtown Toronto in this modern one-bedroom condo just steps from the CN Tower, Rogers Centre, and the waterfront. The unit features a comfortable queen bed in the bedroom and a sofa bed in the living room, perfect for couples or small groups. Enjoy skyline views through floor-to-ceiling windows or relax on the private balcony. The condo includes a full kitchen, smart TV, high-speed Wi-Fi, and in-suite washer and dryer. Guests also have access to a gym and outdoor pool .

“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”

Toronto Vacation | ➊ The One Toronto Villa
The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

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!

DownTown2Bd 2Bath W Stunning View STEP To CN Roger
This is a fully furnished 2 BED + 2FULL BATH. CORNER UNIT Free Parking included/Full kichen WITH Greatest Balcony with View of the CN Tower and Rogers Centre. Scotia arena .Aquarium Ripleys, Lake,Union Station ,MTCC Only 2 min walk to All above+15 min Walk to museium + City Hall+ Eaton Center Mall +path to longoes+star+Lcbo Starbox+scotia arina+tens of other places and fine resturants. Highlights: → Secured building access with 24/7 concierge

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 !

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.

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.
Popular amenities for York rentals with a pool
House rentals with a pool

King West Studio – TIFF, Dining & Nightlife

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

Spacious, Pet Friendly Basement Apartment

Luxe Haven Heated Pool Sauna Gym

Beautiful Oasis In the city with Heated Pool

HEATEDPool/HotTub CN Tower Rogers Centre

Luxury 4BR Designer Retreat with Heated Wave Pool

Leaside Rental w/ Backyard& Pool
Condo rentals with a pool

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

Luxury Downtown Condo For 6 (CN Tower View)

Yorkville Luxury Suite | Pool, Sauna & Gym Toronto

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

Stylish Downtown Toronto Condo + Free Parking

Charming Condo w Parking, CN Tower View & Pool

Central downtown condo next2 CNtower+free parking

Modern 1+Den condo steps away from CN Tower & Lake
Other vacation rentals with a pool

Lux Top-Floor w/ CN Tower Views

Cityscape Oasis w/ Private Patio & Parking

Private 1 bed/1.5 bath in-law suite in a house!

1 Bedroom-King bed with parking steps to the lake

Charming lakeview suite + parking

Resort Style Lake View Condo

private backyard SPA oasis in Toronto

Tranquil Estate Retreat | Pool, Pond on 3 Acres
When is the best time to visit York?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$16,495 GYD | G$16,704 GYD | G$16,704 GYD | G$19,418 GYD | G$21,298 GYD | G$21,924 GYD | G$21,298 GYD | G$21,924 GYD | G$21,089 GYD | G$19,001 GYD | G$19,210 GYD | G$19,210 GYD |
| 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 |
Destinations to explore
- Rentals with a hot tub York
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- Rentals with pools Toronto
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- Rentals with pools Canada
- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Niagara Falls
- Toronto Eaton Centre
- Niagara Falls State Park
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Coca Cola Coliseum





