
Holiday rentals with a pool in Midtown
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Midtown

Total holiday rentals
Explore 350 holiday rentals in Midtown

Nightly prices starting at
Midtown holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 5,710 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 100 rentals that welcome pets

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
340 of Midtown holiday rentals include wifi 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 Evergreen Brick Works
Top-rated rentals with a pool in Midtown
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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.

Midtown Penthouse - Toronto City Skyline View
Stunning one bedroom penthouse apartment in the heart of midtown Toronto (Yonge & Eglinton). 5 min walk to Eglinton Station, 15 min commute to downtown. Enjoy spacious 10 ft ceilings and a south-facing, fully unobstructed view of the CN Tower / city skyline. 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) on the main floor of the building. Great restaurants nearby.

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

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 .

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.

Midtown 1BR | Workspace, Parking + Sofa Bed
Enjoy a comfortable Midtown Toronto stay with a dedicated workspace, high-speed Wi-Fi, flexible sleeping space, and included parking — ideal for couples, solo travellers, small families, or guests combining work and leisure. Restaurants, cafés, and pubs are a short walk away, with the subway only 5 minutes away for easy access to downtown Toronto and major attractions. Loblaws and LCBO are also accessible directly through the building’s parking garage. Registration number: STR-2406-HTPBPY

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.

Luxury Retreat in Yorkville | Pristine Amenities!
Welcome to our stylish and luxurious Yorkville condo! Immerse yourself in the heart of Toronto's most upscale neighbourhood, surrounded by top-rated shopping, renowned restaurants, and cultural attractions. This chic retreat offers modern amenities, elegant design and a prime location for an unforgettable stay in a newly-constructed building. ➜ Approx. 600ft² / 56m² of space ➜ Highspeed WIFI ➜ In-unit washer & dryer ➜ Fully equipped kitchen ➜ Steps to Bay & Museum subway stations

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.

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.

Modern 2BR 2BATH Urban Core Hotel-Style Condo
Consistently ranked among Toronto’s top condos and hosts, this upscale, fully furnished two-bedroom, two-bathroom suite is in the heart of the Entertainment and Theatre District. Steps from the CN Tower and Union Station, and moments to the Rogers Centre, Scotiabank Arena, MTCC, Ripley’s Aquarium, AGO, and TIFF. Enjoy arrival essentials, luxury hotel-style amenities, iconic renovated outdoor rooftop pool, and a fully equipped home for families or business guests.
Popular amenities for Midtown rentals with a pool
House rentals with a pool

Toronto Pool Retreat

King West Studio – TIFF, Dining & Nightlife

Ravine Paradise ! heated pool and hot tub!

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

Leaside Rental w/ Backyard& Pool

Luxury 4BR Designer Retreat with Heated Wave Pool

Private Pool Lakeview House

Luxury Spa Escape with Pool & Jacuzzi
Apartment rentals with a pool

Artsy and Comfy Home with a View

Rooftop Pool Condo with CN Tower View

**30%OFF** Lake view property ❤️ of downtown

Luxury Downtown Condo For 6 (CN Tower View)

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

Charming Condo w Parking, CN Tower View & Pool

Stylish 1BR on Toronto’s Harbourfront
Other holiday rentals with a pool

Fully furnished XL bachelor unit

Modern New 2Bd 2Ba+Den Condo with Balcony

Modern 1Bd+Den Condo with Balcony Lillian St

Downtown Resort Pool | Walk Score 99

Luxury Yorkville APT w/Pool + Spa

Spacious 3BR - Free Parking - 5 min walk to Subway

Park Regal Yorkville

Downtown Toronto 1+1 by UofT & Subway
When is the best time to visit Midtown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $142 SGD | $140 SGD | $155 SGD | $167 SGD | $191 SGD | $219 SGD | $170 SGD | $182 SGD | $178 SGD | $158 SGD | $144 SGD | $141 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Destinations to explore
- Townhouse rentals Midtown Toronto
- House rentals Midtown Toronto
- Luxury rentals Midtown Toronto
- Bed and breakfasts Midtown Toronto
- Apartment rentals Midtown Toronto
- Rentals with lake access Midtown Toronto
- Family-friendly rentals Midtown Toronto
- Flat rentals Midtown Toronto
- Rentals with a sauna Midtown Toronto
- Pet-friendly rentals Midtown Toronto
- Rentals with breakfast Midtown Toronto
- Rentals with a hot tub Midtown Toronto
- Loft rentals Midtown Toronto
- Private suite rentals Midtown Toronto
- Rentals with pools Toronto
- Rentals with pools Ontario
- Rentals with pools Canada
- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Niagara Falls State Park
- Toronto Eaton Centre
- Niagara Falls
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Yorkdale Shopping Centre
- Casa Loma
- Trinity Bellwoods Park
- Sheppard–Yonge Station
- York University
- Massey Hall
- The International Centre
- Coca Cola Coliseum





