Vacation rentals with a pool in Midtown

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Midtown

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

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Guest favorite
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.
Condo in Yorkville
4.99 out of 5 average rating, 84 reviews

Luxury Stay in Yorkville Prime Toronto Location

Indulge in luxury living at this beautifully furnished 1-bedroom apartment, ideally located in the prestigious Yorkville neighborhood of Toronto. Designed for comfort and style, this serene retreat features high-end finishes and a warm, welcoming ambiance. Just steps from Toronto’s main transit line, you’ll be surrounded by designer boutiques, renowned art galleries, chic cafés, stylish bars, and top-rated restaurants. Whether you’re here to shop, explore, or relax, enjoy the this upscale suite.

Guest favorite
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.
Condo in Entertainment District
4.92 out of 5 average rating, 101 reviews

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.

Guest favorite
The open-concept living area features a gray couch and a small round coffee table, complemented by a patterned area rug. A dining set with yellow chairs is placed near the kitchen, which showcases modern appliances and sleek cabinetry.
Guest suite in Eglinton West
4.85 out of 5 average rating, 157 reviews

Modern Private Suite By Subway w Free Parking

An entire floor is yours to use privately. Newly renovated with modern amenities, includes a 55" Smart OLED TV, Fibre Optic High-Speed WIFI, and backyard full of fun activities for couples and families. Next to public transit, a quick walk away, is TTC Eglinton W station. Centrally located, quick access to downtown or any neighbouring city (Vaughan, Markham, Brampton, Mississauga). Situated on a quiet street and walking distance from grocery stores, pharmacies, coffee shops, and eating places.

Top guest favorite
A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.
Condo in Yorkdale
5 out of 5 average rating, 128 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

Guest favorite
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.
Condo in Entertainment District
4.93 out of 5 average rating, 122 reviews

Charming Condo w Parking, CN Tower View & Pool

Enjoy your stay at a charming & modern condo located in the heart of downtown Toronto. Stop settling for sub-par accommodations, and treat yourself to this fully equipped, meticulously cleaned unit with 1 Queen Bed + 1 Sofa Bed. You will be within steps (literally) to the CN Tower, Rogers Center, Ripley’s, and many of Toronto’s top attractions. I am an extremely passionate & attentive host who will cater to your requests and desires. Shoot me a message to get started on your Toronto getaway.

Top guest favorite
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.
Condo in Entertainment District
4.98 out of 5 average rating, 128 reviews

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

Enjoy your luxury condo in heart of Entertainment District. Best location in the downtown! Very close to all major attractions but silence and comfortable to enjoy city life. Breathtaking view, step away from CN Tower, Aquarium, Metro Convention Centre, Rogers Centre, TiFF, Union Station, Scotiabank Arena, Lake Ontario and others Outdoor pool in 15th floor with CN Tower view (seasonally open), gym area with new equipments, hot tub, steam room and other amenities ready for your leisure

Guest favorite
A modern dining area is highlighted by a wooden table accompanied by four metal stools. Above, a stylish light fixture with multiple bulbs adds warmth to the space. A spacious living area with large windows can be seen in the background, offering an abundance of natural light.
Condo in North Toronto
4.8 out of 5 average rating, 70 reviews

Luxury Midtown Condo with Pool and Gym, Parking

We are hosting guests in this property for more than 2 years, however we had to create a new listing to comply with city regulations. You can find all of our reviews in our old listing: https://www.airbnb.ca/hosting/listings/editor/53566665/view-your-space Enjoy a stylish experience at this centrally located, large, and elegant unit in a brand new condominium with magnificent views. Free parking + pool gym + hot tub. This 1 bedroom + Den unit is located in the heart of midtown Toronto.

Guest favorite
A bright bedroom features a queen-sized bed with soft linens, set against a large window that allows natural light to fill the space. A round mirror hangs on the wall above a sleek dresser, and a small plant adds a touch of greenery.
Condo in North Toronto
4.85 out of 5 average rating, 121 reviews

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.

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, 161 reviews

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 go for walks on the boardwalk ! 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.

Top guest favorite
A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.
Apartment in Fort York
4.99 out of 5 average rating, 132 reviews

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. 

Top guest favorite
A comfortable living room is showcased with a gray sofa and a glass coffee table. A flat-screen TV is placed on a low black stand. Natural light filters through the partially closed blinds, creating a warm atmosphere. An artwork adorns the wall, adding a touch of elegance.
Condo in North Toronto
4.99 out of 5 average rating, 76 reviews

Midtown Toronto Condo!

This vibrant midtown building is surrounded by diverse dining options, from restaurants to pubs, all within 1-10 minutes’ walk. The subway is just 5 minutes away, offering quick access to Rogers Centre (15 km) and Scotiabank Arena. A nearby bus stop connects you to the rest of the city. Conveniently, the building provides direct access to a Loblaws supermarket and LCBO through the parking garage. Registration number: STR-2406-HTPBPY

Top guest favorite
Condo in North Toronto
4.97 out of 5 average rating, 31 reviews

1Bd+ Den Cozying Apartment in Midtown Toronto

Cozy one bedroom plus a Den apartment in the heart of midtown Toronto (Yonge & Eglinton). 5 min walk to Eglinton subway Station, 15 min commute to downtown. Free underground parking included. Building amenities include: gym, salt water pool, hot tub, sauna, steam room, outdoor patio + BBQs. There is Loblaws (grocery) and LCBO (liquor) at the main floor with direct access to the building. Great restaurants nearby.

Popular amenities for Midtown rentals with a pool

When is the best time to visit Midtown?

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Quick stats about vacation rentals with a pool in Midtown

  • Total vacation rentals

    Explore 370 vacation rentals in Midtown

  • Nightly prices starting at

    Midtown vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 5,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    360 of Midtown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Midtown rentals

  • 4.8 Average rating

    Midtown stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Midtown's top spots, include Casa Loma, Royal Ontario Museum, and Christie Pits Park

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