Holiday rentals with a pool in Church-Wellesley

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Church-Wellesley

  • Total holiday rentals

    Explore 70 holiday rentals in Church-Wellesley

  • Nightly prices starting at

    Church-Wellesley holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 910 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    70 of Church-Wellesley holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Church-Wellesley rentals

  • 4.8 Average rating

    Church-Wellesley stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated rentals with a pool in Church-Wellesley

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A stylish living area features a leather sofa and an accent chair, creating a cozy seating arrangement. A modern coffee table is positioned centrally, with a small plant and decorative items. The open kitchen area includes sleek cabinetry and a microwave, enhancing the contemporary design.
Apartment in Yorkville

Yorkville Luxury Suite | Pool, Sauna & Gym Toronto

Experience best of Yorkville, Toronto’s most prestigious neighborhood. This stylish, furnished condo features a comfortable queen bed, modern living space, dedicated workspace, high-speed Wi-Fi, and fully equipped kitchen for the seamless stay. Enjoy premium amenities including fitness centre, pool, hot tub and sauna. Just steps from world-class dining, luxury shopping, art galleries, and University of Toronto, it’s the perfect home base for business travelers, couples, and city explorers alike.

LocationValueBathroom

4.98 out of 5 average rating, 103 reviews
Guest favourite
A well-appointed living area features a dark accent wall adorned with decorative plates. A low coffee table sits in front of a comfortable sofa, illuminated by a nearby lamp. Sheer curtains allow natural light to filter in from large windows, creating a bright atmosphere.
Apartment in Downtown Toronto

Welcome to the Heart of Toronto- Steps to Subway

Located in vibrant Church-Wellesley Village, this stylish 1-bedroom + office den condo offers comfort and convenience in one of Toronto’s most dynamic neighbourhoods. Just 150 meters from the subway, surrounded by cafés, vibrant markets, ethnic grocers, and Eaton Centre. Ideal for short or extended stays, the space features a fully equipped kitchen, a bright living area with natural light, and a dedicated workspace for remote professionals — thoughtfully arranged for comfortable everyday living.

LocationViewGetting around

4.82 out of 5 average rating, 87 reviews
Top guest favourite
A comfortable living area is presented with a light-colored sectional sofa and a brown leather armchair. A modern entertainment unit displays a flat-screen television, complemented by framed artwork on the walls. A soft area rug partially covers the wooden floor, enhancing the inviting atmosphere.
Apartment in Downtown Toronto

Luxury Downtown Condo For 4 (CN Tower Views)

Step into luxury at this stylish condo that sleeps 4 nestled in the vibrant Entertainment District. Immerse yourself in city life with proximity to iconic attractions such as the CN Tower, Metro Convention Centre, Rogers Centre, & Scotia Bank Arena—all just steps away. A short stroll leads you to an array of upscale dining, shopping, and entertainment options. Enjoy the modern and tranquil ambiance we've curated within the unit, while taking in the breathtaking CN Tower view from the balcony.

LocationValueNearby

4.93 out of 5 average rating, 123 reviews
Top guest favourite
Apartment in Downtown Toronto

Luxury Downtown Condo For 6 (CN Tower View)

Luxury awaits in our sophisticated 2bed, 2bath condo in the Entertainment District. This prime location places you steps away from Toronto's CN Tower, Metro Convention Centre, Rogers Centre, Hockey Hall of Fame & Scotia Bank Arena. Within a short walk, explore plenty of top dining, shopping, and entertainment options. Our unit is meticulously designed for modernity, elegance, and a truly relaxing experience. Enjoy our updated balcony with seating arrangements & breathtaking CN Tower views.

LocationFamilyTV

4.98 out of 5 average rating, 129 reviews
Guest favourite
Flat in Downtown Toronto

Downtown Resort Pool | Walk Score 99

Experience downtown Toronto in this stylish 1+1 bedroom apartment, comfortably hosting up to 6 guests. Stunning city views, a fully equipped kitchen, high-speed Wi-Fi, and in-unit laundry. Resort-style amenities including an indoor pool, hot tub, gym, and sauna. Perfectly located steps from Wellesley Subway, U of T, TMU, and Eaton Centre. Unparalleled access to Toronto's best dining, shopping, and attractions. Ideal for business travelers, couples, or families seeking a vibrant urban stay.

ValueLocationHospitality

4.88 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Downtown Toronto

Private Cozy Downtown Condo

Centrally located in Toronto, this apartment fits 4 people and boasts full access to amenities, in unit laundry, and a brief walk to the North and South Subway lines to navigate and explore the city with ease. 736 Bay Street promises a comfortable stay for any working professional, a family visiting sick kids or any of the surrounding hospitals, friends looking to discover the vibrant city, and everything in between. Parking is available, pets ARE permitted, and this is a non-smoking unit.

LocationFamilyGetting around

4.93 out of 5 average rating, 105 reviews
Guest favourite
Flat in Downtown Toronto

Stunning Skyline View Condo, Steps to CN Tower

Stay in the heart of downtown Toronto in this modern one-bedroom condo just steps from the CN Tower, Rogers Centre, and the waterfront. The unit features a comfortable queen bed in the bedroom and a sofa bed in the living room, perfect for couples or small groups. Enjoy skyline views through floor-to-ceiling windows or relax on the private balcony. The condo includes a full kitchen, smart TV, high-speed Wi-Fi, and in-suite washer and dryer. Guests also have access to a gym and outdoor pool .

LocationFamilyKitchen

4.93 out of 5 average rating, 160 reviews
Superhost
The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.
Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

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.

ValueLocationView

4.92 out of 5 average rating, 217 reviews
Superhost
Flat in Downtown Toronto

Stylish 1BR in Heart of Downtown | Steps to Subway

This modern 1-bedroom condo is ideal for travelers, couples, small families looking to experience the best of the downtown core. Step inside and unwind in a comfortable bedroom with Queen size bed, a bright living area with Smart TV, fast Wifi and all the essentials. Location is everything, and you’ll be right in the center of it all. Just a short walk to the subway, getting around the city is quick and effortless. You’re also surrounded by shops, restaurants, cafés, and entertainment

ValueLocationHot tub

4.85 out of 5 average rating, 20 reviews
Guest favourite
A spacious open concept living area features light wooden flooring and modern furnishings. The kitchen is equipped with stainless steel appliances and a large island. Natural light floods in through floor-to-ceiling windows, highlighting a stylish area rug with circular patterns and a cozy seating arrangement.
Loft in Downtown Toronto

Modern Downtown Loft with Private Garden

Welcome to this modern and spacious (765 square feet / 71 square meters) one bedroom condo loft in the prestigious Verve Residences and Lofts located minutes away from Yonge & Bloor, Yorkville, the Village, Yonge & Dundas Square, the University of Toronto, two Subway lines and countless other Toronto landmarks, museums and restaurants. This condo loft features luxurious finishes & decor, a king size bed, as well as a rarely found private entrance and garden in the centre of the city.

FamilyLocationAir conditioning

4.88 out of 5 average rating, 117 reviews
Guest favourite
A bright living area is featured with an open-concept layout, showcasing a modern kitchen with sleek appliances and a dining table surrounded by black leather chairs. Floor-to-ceiling windows offer ample natural light, while a cozy seating area provides a welcoming atmosphere.
Apartment in Downtown Toronto

College Park :2Bd+2bth + Free parking

950 sq.ft. luxurious 2 Bed 2 Bath including underground parking. In the coveted Bay and College neighbourhood. 5-10min walk to University, Queens Park, Dundas Square,Eaton Centre, Yorkville,ROM, City Hall,Nathan Philips SquareChurch Street, UofT, Ryerson 20-25 minute walk to CN Tower;Rogers Center 3 Min : Womens Hospital, 7 mins to Toronto General Hos Loblaws, 24 hr Metro Walking Distance to 3 subway stations (Wellesley,Queens Park,College Station). Pool,Gym,Hot Tub

LocationFamilyView

4.93 out of 5 average rating, 227 reviews
Top guest favourite
A round marble dining table is featured in the center, surrounded by wooden chairs. Above hangs a stylish light fixture. A decorative hockey-themed wall art is displayed, reflecting local culture. The open kitchen area includes modern appliances and a neutral color scheme, enhancing the inviting space.
Flat in Downtown Toronto

Canadiana Downtown Condo w/King Bed + Free Parking

We pride ourselves on delivering a 5 star hotel-like experience!! Condo offers FREE PARKING inside of the building. Whether you're in town for a concert, sporting event, business trip or just to catch some local touristic hotspots, you'll be within 8min walk of your destination. Condo is attached to Scotiabank Arena + Union. The condo has a King Bed and 2 Queens to comfortably accomodate your large group. Book now there's a surprise waiting inside!

ValueFamilyQuiet

4.92 out of 5 average rating, 181 reviews

Popular amenities for Church-Wellesley rentals with a pool

Apartment rentals with a pool

Guest favourite
A bright living space showcases a comfortable sofa beside a round glass table. A large TV is mounted on a textured wall. Natural light floods in from floor-to-ceiling windows, revealing city views, while a cozy bedroom is visible through an open doorway.
Apartment in Downtown Toronto

Stylish 1BR on Toronto’s Harbourfront

FamilyLocationGetting around

4.93 out of 5 average rating, 123 reviews
Top guest favourite
A light-filled bedroom features a spacious bed dressed in crisp white linens. Two bedside tables with lamps stand on either side. A large window provides a glimpse of the city outside, complemented by a decorative indoor plant and modern wall art.
Apartment in Downtown Toronto

Luxury Downtown Condo For 6 (Near CN Tower)

ValueFamilyAccess

4.97 out of 5 average rating, 191 reviews
Guest favourite
A modern living area is highlighted by large windows offering views of the outside. A spacious sectional sofa is complemented by decorative cushions. A sleek kitchen island with stone countertops provides ample space, and a dining area is visible, accented by natural light.
Apartment in Downtown Toronto

3BR Penthouse with Panoramic Views + Large Terrace

ValueFamilyGetting around

4.89 out of 5 average rating, 115 reviews
Superhost
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.
Apartment in Downtown Toronto

Beautiful Condo Across CN Tower and MTCC

LocationFamilyParking

4.84 out of 5 average rating, 164 reviews
Top guest favourite
A modern living area features a grey sectional sofa paired with a wooden coffee table. Natural light streams through large windows, revealing a view of the city. A 55-inch Smart TV is positioned on a dark wood console, complemented by decorative elements on the table.
Apartment in Downtown Toronto

Charming Condo w Parking, CN Tower View & Pool

FamilyValuePool

4.94 out of 5 average rating, 148 reviews
Guest favourite
The kitchen features modern appliances and a sleek countertop, while a dining table with six chairs occupies the central space. A vibrant artwork adorns the wall, and large windows provide a view of the cityscape, letting in natural light.
Apartment in Downtown Toronto

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

FamilyLocationSleep quality

4.95 out of 5 average rating, 152 reviews
Guest favourite
A well-furnished living area is shown, featuring a dark leather couch, a round wooden coffee table, and a comfortable chair. A large flat-screen TV is positioned on a media console, while natural light enters through expansive windows, revealing a light-colored rug and decorative plants.
Apartment in Downtown Toronto

Luxury 1 Bedroom Suite In Heart Of Toronto

LocationFamilyAccuracy

4.91 out of 5 average rating, 343 reviews
Guest favourite
Apartment in Downtown Toronto

BEST Loc Period/ 62% OFF on monthly lease/parking

ValueLocationGetting around

4.78 out of 5 average rating, 186 reviews

Other holiday rentals with a pool