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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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Top guest favorite

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 389 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...

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Scarborough

4.95 out of 5 average rating, 111 reviews

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

Top guest favorite

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

4.94 out of 5 average rating, 126 reviews

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.

Top guest favorite

An outdoor swimming pool is centered within a landscaped courtyard, surrounded by contemporary apartment buildings. Comfortable lounge chairs line the pool deck, while a graceful pathway leads to the water's edge. Lush greenery frames the area, enhancing the tranquil atmosphere.

Condo in North York

5 out of 5 average rating, 100 reviews

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

A residential backyard features a swimming pool with crystal-clear water, accompanied by a diving board. Lounge chairs are positioned nearby, and a deck area with sliding doors complements the brick exterior of the house. A sliding water slide adds to the recreational space.

Guest suite in Lorne Park

4.92 out of 5 average rating, 160 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

Top guest favorite

Apartment in Newmarket

4.99 out of 5 average rating, 185 reviews

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.

A modern living area features a sleek kitchen equipped with stainless steel appliances, including a microwave and oven. A comfortable sofa is positioned beside a large window, offering natural light. A breakfast bar with stools enhances the inviting space, which includes a neutral-toned area rug.

Condo in Unionville

4.93 out of 5 average rating, 27 reviews

Modern Downtown Unionville Stay

Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

Top guest favorite

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

4.99 out of 5 average rating, 151 reviews

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

Top guest favorite

A bright and airy living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central rug, while a wall-mounted television provides entertainment. The entrance is visible with a stylish door and greenery outside.

Home in North York

4.88 out of 5 average rating, 86 reviews

Casa Meya - Toronto Poolhouse Villa

Casa Meya : This exclusive modern and fully renovated Villa at 2024. Upper Floor : Beautiful Kitchen with brand new Bosch and LG appliances. An Island to host 4 guests plus a 6 seats Dining Table. 85" Samsung QLED TV to watch included Premium TV channels. Master Bedroom ( KING ) - 65" TV / 1st Bathroom 2nd Bedroom ( QUEEN ) - 42" TV / 2nd Bathroom Lower Floor : 3rd Bedroom ( QUEEN ) - 42" TV / 3rd Bathroom

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

4.84 out of 5 average rating, 276 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.

A spacious backyard features a sun-drenched inground pool surrounded by a stone patio and mature perennial gardens. A cozy seating area is positioned next to the pool, while a charming shed and upper deck are visible in the background, enhancing the outdoor retreat.

Apartment in Milton

4.84 out of 5 average rating, 171 reviews

Backyard Oasis Guesthouse.

Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

An outdoor pool is surrounded by a wooden deck and shaded by lush greenery. Several lounge chairs are positioned along the edge, providing relaxing spots. A small building with flower boxes is visible in the background, enhancing the natural setting.

Guest suite in Markham

4.96 out of 5 average rating, 51 reviews

Hidden Gem of Thornhill [Ravine+Pool+NEW hot tub]

Nested at the end of a quiet cul-de-sac. Backing the ravine and siding the golf course. Brand new, recently renovated walk-out lower level unit, same level as the backyard with a magnificent view of the ravine. This is your escape from the city within the city! Pool will be open from Early June. New Outdoor Hot Tub now open and ready to use! **Absolutely NO event/Party allowed in the property**

Vacation rentals for every style

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Popular amenities for Richmond Hill rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

An open-concept living area is flooded with natural light, featuring a modern white sectional sofa on a plush rug. The space includes a kitchen with sleek cabinetry, a dining area visible in the background, and large glass doors that open to the outdoors.

Home in Vaughan

5 out of 5 average rating, 12 reviews

Vacation Getaway with Heated Spa-Pool Open365 Days

Home in North York

5 out of 5 average rating, 20 reviews

Award Winning Luxury Home with Heated Pool + Sauna

An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.

Home in Port Perry

4.93 out of 5 average rating, 226 reviews

Home away from home with a hot tub and pool

A newly renovated pool is surrounded by a spacious stone deck, complemented by a shaded cabana in the background. Lush greenery and tall trees frame the area, creating a serene outdoor setting ideal for relaxation.

Home in Orangeville

5 out of 5 average rating, 8 reviews

Hockley Valley - Jazzy Pines - 4 BR with Pool

A balcony features a round table with two wicker chairs, surrounded by vibrant flowering plants in hanging baskets and pots. In the background, a sparkling blue pool is visible, nestled within a fenced backyard shaded by greenery.

Home in Newmarket

4.86 out of 5 average rating, 28 reviews

Cozy Pool house in Newmarket

Top guest favorite

A heated swimming pool surrounded by lush greenery reflects the clear sky above. The pool is framed by a glass fence and features colorful pool toys floating on the surface. A pergola provides shaded seating along the spacious deck, inviting outdoor relaxation.

Home in Scarborough

4.98 out of 5 average rating, 59 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

An outdoor space features a spa-inspired pool with connected Jacuzzi, surrounded by lounge chairs and an umbrella. A large gazebo housing a dining area is visible, along with landscaped greenery and a clear blue sky enhancing the serene environment.

Home in North York

5 out of 5 average rating, 5 reviews

Luxury Spa Escape w/ Pool & Jacuzzi + Private Chef

A private backyard features a heated saltwater pool with a waterfall, surrounded by lush greenery. A covered gazebo offers seating options, while a dining area with patio furniture is visible. The space is accessed through a glass sliding door from the interior.

Home in North York

5 out of 5 average rating, 19 reviews

Luxe, Family-Friendly Oasis Home With Outdoor Pool

Condo rentals with a pool

An indoor swimming pool area is featured, with clear water inviting relaxation. A stainless steel handrail provides stability for entry, while large windows allow natural light to illuminate the space. The area is equipped with tiled flooring and a clock on the wall for convenience.

Condo in Davisville Village

4.85 out of 5 average rating, 111 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

A panoramic balcony view reveals the iconic CN Tower alongside city skyline reflections on a modern glass building. Red outdoor seating provides a contemporary touch, surrounded by a spacious tile floor that invites relaxation amidst the urban landscape.

Condo in Downtown Toronto

4.88 out of 5 average rating, 133 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Condo in Mississauga

4.87 out of 5 average rating, 181 reviews

Beautiful Penthouse with Breathtaking View

A bright living area features a modern orange sectional sofa and a wooden coffee table. Large windows offer views of the cityscape. A dining area with high chairs is positioned beside a compact kitchen, with red cabinetry adding a pop of color.

Condo in Downtown Toronto

4.9 out of 5 average rating, 107 reviews

Beautiful Condo Across CN Tower and MTCC

A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.

Condo in Downtown Toronto

4.97 out of 5 average rating, 250 reviews

Chic, High-Rise Apartment with CN Tower Views

Top guest favorite

A chic living area features a gray chaise sofa adorned with pastel pillows, complemented by light pink curtains. A marble-top dining table sits near a flat-screen TV mounted on the wall, while a decorative bowl adds a touch of elegance to the coffee table.

Condo in Fort York

4.98 out of 5 average rating, 200 reviews

Stylish Downtown Toronto Condo with Free Parking

A comfortable living area features a sofa adorned with decorative cushions and two accent chairs. A cozy area rug with geometric patterns lies beneath, while a dining bar with seating for four is visible in the open-concept kitchen, complemented by stainless steel appliances.

Condo in Davisville Village

4.93 out of 5 average rating, 163 reviews

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

The outdoor pool is surrounded by lounge chairs, inviting relaxation. Soft lighting accentuates the area, creating a serene atmosphere as evening approaches. Modern structures and seating arrangements are visible in the background, enhancing the space's appeal.

Condo in Downtown Toronto

4.92 out of 5 average rating, 288 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

Other vacation rentals with a pool

An outdoor area features a gently curving pool surrounded by a spacious deck. A gazebo offers shaded seating, while decorative structures and planters add visual interest. Lush greenery borders the space, creating a calm and inviting atmosphere.

4.93 out of 5 average rating, 55 reviews

Beautiful Cottage in Ajax

Top guest favorite

A bright living area features a light beige sofa with blue accent pillows, paired with a round coffee table displaying a small plant. Natural light fills the space through a large window overlooking greenery. A soft area rug adds warmth, complemented by a decorative floor lamp.

Apartment in Central Etobicoke

5 out of 5 average rating, 37 reviews

Charming Condo with Private Terrace in Etobicoke!

A serene landscape is captured, showcasing a calm river surrounded by lush greenery. Various structures, including gazebos and outdoor seating, are visible along the riverbank, while a swimming pool and well-maintained lawn provide inviting spaces for relaxation.

Home in Holland Landing

4.97 out of 5 average rating, 29 reviews

Private river access with pool, canoes, kayak

A bright living room features a large leather sofa positioned near floor-to-ceiling windows, allowing natural light to fill the space. A modern coffee table sits in front, and framed artwork is displayed on the walls, creating a comfortable and inviting atmosphere.

Condo in Unionville

4.6 out of 5 average rating, 43 reviews

Luxury Hotel Condo - Modern gym, Swim Pool & Bars

Top guest favorite

A modern living area features a sleek sofa paired with a round coffee table. A flat-screen TV is mounted on the wall, providing entertainment options. Light streams in through large windows, illuminating the neutral color palette and contemporary decor. A standing lamp and wall art add subtle detail.

Condo in North York

4.95 out of 5 average rating, 42 reviews

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

An inviting swimming pool sits surrounded by natural stone decking, reflecting a bright blue hue under the sunlight. The two-story retreat is visible in the background, featuring a mix of brick and siding, with outdoor seating areas situated on the deck.

Home in Cedar Valley

4.8 out of 5 average rating, 15 reviews

Forest House | Golf/Hiking/Horse Riding Nearby

The kitchen area features modern stainless steel appliances with a minimalist design. A large window allows natural light to illuminate the space, highlighting the sleek cabinetry and stylish backsplash. A small sitting area is visible in the background, enhancing the open-concept layout.

Condo in Mimico-Queensway

4.92 out of 5 average rating, 12 reviews

Luxury 1BD Condo w/ Stunning Views - Toronto

Home in Port Credit

4.93 out of 5 average rating, 15 reviews

Oakwood Haven

Quick stats about vacation rentals with a pool in Richmond Hill

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

Destinations to explore