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

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...

Lux Condo w/ Free Parking, King Bed, Clean, Quiet
Free underground parking! (Very hard to find in downtown Toronto) Renovated condo great for business travelers, remote workers, and arguably the best location for tourists in the city. One of Toronto’s top luxury, Airbnb-friendly buildings. 300 Front Street West sits directly across from the CN Tower and Blue Jays Stadium, just a 3-minute walk to the Rogers Centre, and in the heart of the city's best restaurants and nightlife. Despite its central location, it stays wonderfully quiet at night.

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

The Hilton BnB Adult Luxury Suite
Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Chic Richmond hill Condo
* World Cup 2026 near Toronto* Just a breezy 25-minute drive to the edge of Toronto, this one-bedroom , one-bathroom space offers a comfortable setting for both short visits and extended stays. The building features an indoor pool, hot tub, gym, and sauna, while the unit includes an equipped kitchen, Wi-Fi and in-suite laundry. With one underground parking spot, a bakery in the lobby, public transit steps from the building, shops and a mall only minutes away. Your pleasant stay awaits!

SpectacularPenthouse VIEWS/ POOL /free Parking
Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

Modern 3-Bedroom Apartment
Welcome to our bright, modern 3-bedroom apartment in the heart of North York, just steps from the subway station! Perfect for families or groups, this stylish space features large windows, modern furnishings, and a fully equipped kitchen. The master bedroom has a queen-size bed and an en-suite bathroom and walk-incloset, the other two bedrooms offer a queen and a full size beds .Enjoy easy access to shopping, restaurants, and a library. With high-speed Wi-Fi and a cozy living area.

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.

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.

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.

Cozy Entire 2 Bedrooms Suite - Good Location
Located in the center of Richmond Hill, this suite offers modern clean accommodations with a relaxing homey atmosphere. There is indoor pool, jacuzzi , Sauna and the air-conditioned gym. Everything you need can be found within walking distance, including many restaurants, a mall, even a large library. You can find many attractions a reasonable distance away, such as Canada's Wonderland, making this a perfect stopping point.

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.
Popular amenities for Richmond Hill rentals with a pool
House rentals with a pool

Luxury House with a Bright Sunroom & a heated pool

newly renovated, close to airport, washer/dryer

Seraya Wellness Retreat

Award Winning Luxury Home with Heated Pool + Sauna

Ravine Paradise ! heated pool and hot tub!

Luxury Spa Escape with Pool & Jacuzzi

Countryside walk-out with pool.

Modern Custom Built Walkout to Marble Pool Game RM
Condo rentals with a pool

Stylish 2 Bdrm Gorgeous CN Tower View w/Parking!

Stylish Downtown Toronto Condo with Free Parking

Charming Condo w Parking, CN Tower View & Pool

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Luxury Downtown Condo For 6 (Near CN Tower)

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

Stylish 1BR/2 bed CN Tower view, Free Parking
Other holiday rentals with a pool

Bright Space w/ Private Patio & Premium Amenities

Spectacular Stay with CN Tower View!

Bright Sun Filled Condo + Pool + Gym, CN Tower

Stoney Creek Suites

Lovely Downtown Suite with Private Balcony

Penthouse 2BR+Den | Skyline Views • SQ1 • Parking

Entire Modern Condo Townhouse in Toronto

Stellar Humber Bay 2BD/2BTH Large Patio & Parking
When is the best time to visit Richmond Hill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $137 AUD | $139 AUD | $176 AUD | $176 AUD | $183 AUD | $196 AUD | $186 AUD | $184 AUD | $204 AUD | $146 AUD | $123 AUD | $132 AUD |
| 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 Richmond Hill

Total holiday rentals
Explore 70 holiday rentals in Richmond Hill

Verified guest reviews
Over 860 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Richmond Hill holiday rentals include Wi-Fi access

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

4.7 Average rating
Richmond Hill stays receive an average rating of 4.7 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- Distillery District
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Toronto City Hall
- Downsview Park




