
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...

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 explore nearby ski trails. 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. In the colder months, enjoy a winter sk

Modern 2 Bd condo near CN tower/MTCC/Rogers Centre
This spacious and modern suite is conveniently located in the heart of Toronto (Front and John Street). It’s situated within the Entertainment District, home to Toronto’s iconic CN Tower (3-5 min walk), Ripley’s Aquarium, Rogers Centre and the Metro Toronto Convention Center (directly across the street). Amenities: Parking Available for Charge Free unlimited high-speed WiFi Smart TVs w/ cable, Youtube & Netflix Fully equipped kitchen Private balcony Rooftop Infinity Pool Gym access & hot tub

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

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.

Elegant Toronto Lakeview Condo 1+1 w. Free Parking
Step into a world of breathtaking, unobstructed lake views from the private balcony of this executive-style condo. The cozy interior blends comfort and style perfectly. Every inch of this compact space is designed for your convenience and relaxation. Located within walking distance of iconic attractions like Rogers Centre, Scotiabank Arena, Billy Bishop Airport, and the vibrant Entertainment District. Perfect for couples, solo adventurers, business travelers, and families (with kids).

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.

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.

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.

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.

Mackenzie Cottage
Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane
Popular amenities for Richmond Hill rentals with a pool
House rentals with a pool

Luxury House with a Bright Sunroom & a heated pool

Beautiful Cottage in Ajax

Award Winning Luxury Home with Heated Pool + Sauna

Ravine Paradise ! heated pool and hot tub!

Luxury Spa Escape with Pool & Jacuzzi

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Toronto Pool Retreat

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

Lux Waterfront Condo Pool Hot Tub Free Parking

Lakeside Condo Studio In Downtown Toronto

Humber Bay Family Friendly condo w Terrace&Parking

Stylish Downtown Toronto Condo with Free Parking

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

Charming Condo w Parking, CN Tower View & Pool

Luxury 1 Bedroom Suite In Heart Of Toronto

Luxury Downtown Condo For 6 (Near CN Tower)
Other holiday rentals with a pool

Modern Condo | Breathtaking Views | CN Tower

The Snug Oasis - Burrow (Near Airport)

Seraya Wellness Retreat

Bright and Airy Guest Suite with Pool

Modern 1 Bed Condo Mississauga

Cedar Escape • Sauna • 10-Acre Private Forest

Separate apartment with pool, on golf course.

Award Winning 3BR Luxury Penthouse •Stunning Views
When is the best time to visit Richmond Hill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 83 | € 83 | € 106 | € 106 | € 110 | € 118 | € 112 | € 111 | € 123 | € 80 | € 85 | € 83 |
| 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 820 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Richmond Hill holiday rentals include wifi 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
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Mount Pocono Holiday rentals
- Capital District, New York Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Laurentides Holiday rentals
- Beachfront rentals Richmond Hill
- Fitness-friendly rentals Richmond Hill
- Apartment rentals Richmond Hill
- Guest house rentals Richmond Hill
- Rentals with a firepit Richmond Hill
- Rentals with outdoor seating Richmond Hill
- Private suite rentals Richmond Hill
- Townhouse rentals Richmond Hill
- House rentals Richmond Hill
- Villa rentals Richmond Hill
- Rentals with lake access Richmond Hill
- Rentals with a patio Richmond Hill
- Flat rentals Richmond Hill
- Rentals with an EV charger Richmond Hill
- Rentals with a hot tub Richmond Hill
- Rentals with a fireplace Richmond Hill
- Cottage rentals Richmond Hill
- Rentals with a washing machine and dryer Richmond Hill
- Pet-friendly rentals Richmond Hill
- Family-friendly rentals Richmond Hill
- Rentals with a sauna Richmond Hill
- Rentals with breakfast Richmond Hill
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Snow Valley Ski Resort
- Toronto City Hall
- Rouge National Urban Park
- Christie Pits Park
- Royal Ontario Museum
- Royal Woodbine Golf Club




