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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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, 215 reviews

Stylish Condo | Walk to BMO Field + FIFA Festivals

Experience downtown Toronto in a stylish condo! Start your day by enjoying coffee on the balcony. Walk to BMO Field (Toronto Stadium) - ideal for concerts, sports & FIFA events. Walk to Exhibition Place, CN Tower, Rogers Centre, Ripley’s Aquarium, restaurants & waterfront. Full kitchen, 2 desks with fast WIFI. Building features a pool, hot tub, sauna, gym, rooftop BBQ, free parking & self check-in. Discounts for 7+ nights & non-refundable bookings. Book your unforgettable Toronto stay today!

Top guest favorite
A modern living area features a spacious sofa paired with two accent chairs. A round coffee table sits in the center, surrounded by a vibrant area rug. Large windows offer ample natural light and city views, while soft accent lighting enhances the ambiance.
Apartment in Entertainment District
4.88 out of 5 average rating, 135 reviews

Luxury CN Tower and Lake View Penthouse Sleeps 10

Experience luxury in our 41st-floor penthouse at 300 Front St W, Toronto. Steps from the CN Tower, this 2 Bedroom + Large Den (3rd Bedroom) offers stunning CITY, LAKE & SUNSET VIEWS. This beautiful apartment features a wrap-around balcony, 5 beds including a king bed, queen sofa bed, and a fully stocked kitchen. Enjoy CN Tower views from every bedroom, 100% Egyptian cotton linens & 4K Ultra HD TVs. Starbucks, a gym and an outdoor rooftop pool with exceptional views. Perfect for up to 10 guests.

Guest favorite
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Lakeview
4.91 out of 5 average rating, 102 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

YES Hot tub and heated pool are open! Forget your worries in this spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. **25+ ID & waiver req**

Top guest favorite
Apartment in Entertainment District
4.92 out of 5 average rating, 140 reviews

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 .

Guest favorite
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 North York
4.94 out of 5 average rating, 200 reviews

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.

Guest favorite
A view from the kitchen showcases a modern living space filled with natural light. A granite countertop highlights sleek appliances, while the background reveals a cozy seating area and a large window with city views. A TV and decorative plant enhance the inviting environment.
Condo in North Toronto
4.92 out of 5 average rating, 50 reviews

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

Welcome to your ideal retreat in Midtown Toronto 👋🏻 , a sophisticated and inviting stay nestled near the vibrant Eglinton Station (🚶🏻4 min walk). This prime location offers guests unparalleled access to a dynamic neighborhood teeming with exceptional dining, cozy cafés, and a plethora of entertainment options. Whether you’re visiting for business, a weekend getaway, or an extended stay, this stylish rental provides the perfect blend of comfort, convenience, and urban excitement.

Guest favorite
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.
Condo in Harbourfront
4.94 out of 5 average rating, 100 reviews

Stylish 1BR on Toronto’s Harbourfront

Discover the ultimate Toronto experience in our fabulous 1BR condo on Yonge Street, right in the heart of downtown. My husband Saeid and I are proud to host you in this vibrant space with unbeatable access to the Harbourfront, CN Tower, and all of Toronto’s top attractions. Enjoy stunning city views from our thoughtfully decorated condo, featuring a fully-equipped kitchen and a cozy bedroom. Plus, access to great amenities for your comfort. Your Toronto adventure begins here!

Guest favorite
Condo in Harbourfront
4.93 out of 5 average rating, 190 reviews

High-Floor w/ Balcony | CN Tower | Scotia | Rogers

Entire stylish and modern condo in the heart of DT Toronto! WALK to Toronto's main attractions: → CN Tower / Aquarium / Rogers Centre (7 mins) → Scotiabank Arena (2 mins) → Union Station (2 mins) → Lake Ontario Waterfront (3 mins) → Direct access to the underground PATH Highlights: → Secured building access with 24/7 concierge → Spacious balcony with patio set → Electrical fireplace → Washer + dryer with detergent →MONTHLY STAYS: Access to fitness centre, pool, sauna!

Guest favorite
A modern living space features a spacious seating area with a gray sofa and a bright orange accent chair. A dining table with plants stands nearby. Natural light floods the room through a glass sliding door leading to a balcony, offering views of the city skyline.
Condo in North Toronto
4.85 out of 5 average rating, 142 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.

Superhost
A spacious living area features a large sectional sofa adorned with decorative cushions. A modern coffee table is centered in front of a wall-mounted TV, providing a focal point. A minimalist console table is present, accompanied by wall art and a plant on display.
Apartment in Entertainment District
4.8 out of 5 average rating, 139 reviews

2BR Across from CN Tower & MTCC

A newly-furnished condo located at the heart of Downtown Toronto guaranteed to maximize your stay with everything at close proximity. This condo has 10 ft ceilings and over 700 sq ft We provide High-speed WiFi, Cable TV, washing machine/dryer, and basic amenities. Explore Toronto right at your doorstep: - Metro Toronto Convention Centre 30m - CN tower/Rogers Centre 210m - Union Station 500m - Harbourfront Centre 700m - Air Canada Centre 900m - TIFF Bell Lightbox

Top guest favorite
Condo in Entertainment District
4.89 out of 5 average rating, 879 reviews

1 Bedroom + Den (Office/Bidet/Balcony) near Rogers

Elegant modern suite in the heart of Entertainment District and 1-min walk to Rogers Centre, Metro Toronto Convention Centre, CN Tower & PATH (Largest Underground Shopping Complex in the world) Perfect for conferences and seasonal travellers. State of the art amenities including high end gym equipment, spin room, steam room, whirlpool pool and roof top pool. Conveniently located at Front & John, my property is your doorstep to Toronto!

Top guest favorite
Condo in North Toronto
4.99 out of 5 average rating, 81 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

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 350 vacation rentals in Midtown

  • Nightly prices starting at

    Midtown vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 5,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    340 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 Royal Ontario Museum, Casa Loma, and Evergreen Brick Works

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