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Vacation 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.

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Condo in Toronto

4.81 out of 5 average rating, 302 reviews

Spacious Downtown (midtown) 2bed 2 bath free parki

In the heart of Midtown (close to downtown), this is a modern 2 Bedroom, 2 Bathroom, 900 square foot loft, in a high rise building. My place is perfect for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets) are welcome too! The condo is in pristine condition with a fully equipped kitchen, living area, two comfy beds, two full piece washrooms and a balcony with all the luxuries and amenities you need. My spot is close to Underground Subway Train Station - Yellow Line, 24/7 Bus Accessible, Yonge Street, 24 hour restaurants, 24 hour grocery store, Bars, Clubs, Restaurants, Movies, Highway 401. There is no shortage of things to do around here. Thank you for considering staying with me during your visit to Toronto. Whether you're coming for business, pleasure, or to visit family, I think you will tremendously enjoy my suite and my neighborhood.

Jul. 24 – 31

$346 CAD per night

Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 215 reviews

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...

Apr. 24 – May 1

$184 CAD per night

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 533 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Dec. 1 – 8

$513 CAD per night

Guest favourite

Villa in Toronto

4.94 out of 5 average rating, 116 reviews

➊ The One Toronto Villa - Indoor Pool&Tennis Court

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.

Sep. 26 – Oct. 3

$1,670 CAD per night

Guest favourite

Cottage in Innisfil

4.94 out of 5 average rating, 151 reviews

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

Nov. 30 – Dec. 7

$495 CAD per night

Guest favourite

Condo in Toronto

4.93 out of 5 average rating, 230 reviews

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.

Jan. 20 – 27

$360 CAD per night

Guest favourite

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Mar. 20 – 27

$246 CAD per night

Guest favourite

Home in Port Perry

4.94 out of 5 average rating, 203 reviews

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

Oct. 14 – 21

$304 CAD per night

Condo in Mississauga

4.78 out of 5 average rating, 189 reviews

Benetton Suite - Square One - 1 BR+Den+1 Parking

The Benetton Suite - Square One - 1 BR + Den + 1 Parking located in the heart of Mississauga, 600m from Square One Mall and 300m from Living Arts Centre. This centrally air-conditioned apartment. includes complimentary high speed wi-fi and 1 private parking free on site. Furnished in top quality style, the apartment has 2 bedrooms, a flat screen TV (with Netflix!), a fully equipped kitchen, dishwasher, microwave, washing machine, dryer with 1 bathroom with a bath.

Dec. 16 – 23

$211 CAD per night

Guest favourite

Home in Toronto

4.91 out of 5 average rating, 264 reviews

King West Victorian Studio Gem

Victorian Century Home Quiet Residential Street in the Heart of Downtown Toronto Overlooks Park + Outdoor Public Pool Open Concept 735 sq ft Sunny, Exposed Brick, Chandeliers Hardwood Floors Throughout Soaring 11' Ceilings Fully Equipped Eat-in Kitchen Private Laundry Private Backyard/Garden Business Traveler Ready Steps to King Streetcar Minutes to Queen & King West Nightlife, Shops, Cafes + Restaurants & King West Theatre District Street Permit Parking

Dec. 9 – 16

$261 CAD per night

Guest favourite

Apartment in Newmarket

5.0 out of 5 average rating, 140 reviews

The Hilton BnB Adult Luxury Suite

A beautifully decorated open concept walkout suite in an elegant 2-story home with all the amenities, accommodates 1-2 adult guests, in Newmarket’s prestigious Stonehaven Estates. The Hilton BnB is located just 30 minutes from downtown Toronto. Dine by the warmth of a fireplace in the winter or relax and have a BBQ poolside in the summer. The suite is spacious and the grounds are breathtaking. Uniquely designed with luxury in mind!

Sep. 4 – 11

$193 CAD per night

Condo in Mississauga

4.82 out of 5 average rating, 221 reviews

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.

May 8 – 15

$217 CAD per night

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Popular amenities for Richmond Hill rentals with a pool

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House rentals with a pool

Guest favourite

Home in Gormley

4.95 out of 5 average rating, 38 reviews

Lovely Home, Big Backyard + Pool

Mar. 24 – 31

$248 CAD per night

Guest favourite

Home in Newmarket

5.0 out of 5 average rating, 7 reviews

Beautiful Pond View stay!

Dec. 22 – 29

$187 CAD per night

Guest favourite

Home in Newmarket

4.82 out of 5 average rating, 17 reviews

Cozy Pool house in Newmarket

May 26 – Jun. 2

$333 CAD per night

Home in Toronto

4.91 out of 5 average rating, 33 reviews

Ravine Paradise with heated pool & hot tub!

Mar. 16 – 23

$475 CAD per night

Guest favourite

Home in Uxbridge

5.0 out of 5 average rating, 15 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Mar. 13 – 20

$374 CAD per night

Guest favourite

Home in Toronto

5.0 out of 5 average rating, 17 reviews

Central Location Near Transit & Shops w/ Parking!

Oct. 22 – 29

$1,069 CAD per night

Home in Ajax

5.0 out of 5 average rating, 9 reviews

Entire Modern Home | Spacious | Near Lake & Park

May 13 – 20

$375 CAD per night

Guest favourite

Home in Toronto

4.93 out of 5 average rating, 97 reviews

Entire house with Pool, ravine, and nature trail

Oct. 9 – 16

$570 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Toronto

4.97 out of 5 average rating, 218 reviews

Chic, High-Rise Apartment with CN Tower Views

Jun. 1 – 8

$478 CAD per night

Condo in Toronto

4.86 out of 5 average rating, 178 reviews

Best View in Downtown 5 Star Luxury 1+1 w/office

May 14 – 19

$312 CAD per night

Guest favourite

Condo in Toronto

4.89 out of 5 average rating, 273 reviews

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE

Sep. 29 – Oct. 6

$712 CAD per night

Guest favourite

Condo in Toronto

4.94 out of 5 average rating, 230 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

Jul. 24 – 31

$545 CAD per night

Guest favourite

Condo in Toronto

4.95 out of 5 average rating, 170 reviews

Upscale Luxurious Condo Free Parking

Aug. 25 – Sep. 1

$324 CAD per night

Guest favourite

Condo in Toronto

4.97 out of 5 average rating, 291 reviews

Beautiful Condo + CN Tower View + Free Parking

May 19 – 26

$597 CAD per night

Guest favourite

Condo in Toronto

4.89 out of 5 average rating, 246 reviews

Closest condo to Rogers Centre/CN tower in Toronto

May 26 – Jun. 2

$425 CAD per night

Guest favourite

Condo in Toronto

4.88 out of 5 average rating, 129 reviews

1 bdrm Condo by CNT Free Parking 39 FLR Stun. View

Sep. 12 – 19

$396 CAD per night

Quick stats about vacation rentals with a pool in Richmond Hill

Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
820 reviews

Destinations to explore