
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...

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.

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.

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins
1,Welcome to my home in the heart of midtown Toronto in the Yonge & Eglinton area! It sleeps three guests comfortably and is an excellent base for your Toronto adventures! 2,With excellent access to public transportation, you can be in downtown within 15 minutes; you are a 5-minute walk from Eglinton Subway Station, 2 mins from TTC, and within walking distance to tons of shops and restaurants. 3,Loblaws (grocery) & LCBO (liquor) on the main floor of the building.

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.

Cozy Condo Next to CN Tower
Experience the best of Toronto in our modern one-bedroom plus one sofa bed condo, ideally located in the vibrant heart of the city. Enjoy breathtaking views from a high floor, offering a perfect retreat for urban explorers and business travelers. With easy access to top attractions, including the iconic CN Tower, and excellent commuting options, our condo combines comfort with convenience, making it the ideal base to discover Toronto's charm and energy.

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.Â

King West Triplex Main FLR PVT APT 1 BDRM Parking
KING WEST TRIPLEX Mainfloor unit is overlooking the Park and has a Pool in front, baseball and tennis courts, ping pong table and enclosed Dog Park! Hardwood floors, 12ft ceilings, private parking in the rear and a private back patio. Pets permitted. Two blocks from King and Bathurst, club, bars/patio restaurant district, and grocery store. Long term: Request 31 nights or more to avoid paying an additional 13% tax.

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE
This beautiful modern 1 bed & q bath suite is located in the heart of downtown Toronto's Entertainment & Financial District - in the prestigious 300 Front Street building in the core of the city. Enjoy a nice dinner on the balcony with a lake and CN Tower view! The building has a fully equiped Fitness center, Outdoor Pool with a 360 degree of the whole city, Steamroom, Whirlpool BBQ

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.

Downtown Markham Unionville
Newer Condo, 2 bedroom entire unit, fully furnished with everything you need as if you were at home; steps to Historic Unionville, Cineplex with VIP Cinema,, Famous Ruth's Steak House, Good Catch Creole Seafood Place; Japanese Restaurant, Go-for-Tea Fusion, Historic Rouge Valley, Great Dining, Pubs, theatre, shopping Malls
Popular amenities for Richmond Hill rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Seraya Wellness Retreat

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

Chic King West Studio – TIFF & FIFA at Your Door

Casa Meya – Toronto Poolhouse Villa
Apartment rentals with a pool

Beautiful Condo + CN Tower View + Free Parking

Beautiful Condo Across CN Tower and MTCC

Luxury Designer Condo, steps to CN tower

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

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

Artsy and Comfy Home with a View

Luxury Downtown Condo For 4 (CN Tower Views)

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

Spectacular Stay with CN Tower View!

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

Modern 1 Bed Condo Mississauga

Luxury Penthouse Suite SQ1

Beautiful Yorkville Luxury Condo

Modern 1-Bedroom in Midtown TO - 4 min Eglinton ST

Resort Style Lake View Condo

Beachside 2BR | CN Tower and lake View + 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 | $123 SGD | $124 SGD | $157 SGD | $157 SGD | $163 SGD | $174 SGD | $165 SGD | $164 SGD | $182 SGD | $130 SGD | $110 SGD | $117 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 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 & 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
70 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
- Pocono Mountains 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
- Rentals with outdoor seating Richmond Hill
- Rentals with a sauna Richmond Hill
- Cottage rentals Richmond Hill
- Apartment rentals Richmond Hill
- Family-friendly rentals Richmond Hill
- Fitness-friendly rentals Richmond Hill
- Guest house rentals Richmond Hill
- Rentals with breakfast Richmond Hill
- Villa rentals Richmond Hill
- Flat rentals Richmond Hill
- Rentals with a washing machine and dryer Richmond Hill
- Rentals with lake access Richmond Hill
- Rentals with a fireplace Richmond Hill
- House rentals Richmond Hill
- Townhouse rentals Richmond Hill
- Rentals with an EV charger Richmond Hill
- Rentals with a firepit Richmond Hill
- Private suite rentals Richmond Hill
- Pet-friendly rentals Richmond Hill
- Rentals with a patio Richmond Hill
- Rentals with a hot tub Richmond Hill
- Rentals with pools Ontario
- Rentals with pools Canada
- 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
- Downsview Park
- Toronto City Hall




