Holiday rentals with a pool in Scarborough

Guest suite in Scarborough Village

A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.

4.89 out of 5 average rating, 107 reviews

Bluffs Private Suite | 25 Min to World Cup | Pool

Enjoy this beautiful, sun-filled private suite with a large secluded fenced yard and pool in a safe, upscale and serene forested neighbourhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles. EV charger (Tesla/J1772).

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.

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.

A well-lit bedroom features a spacious bed with neatly arranged towels. Two nightstands flanking the bed hold lamps. A desk and chair are positioned by the window, complemented by greenery. A large mirror and a TV are mounted on the wall, enhancing the relaxed atmosphere.

4.98 out of 5 average rating, 112 reviews

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.

5 out of 5 average rating, 136 reviews

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

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

4.92 out of 5 average rating, 138 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 .

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.

4.92 out of 5 average rating, 319 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

This Chic, Upscale Suite Is A Luxurious Home Base In The Heart Of Toronto's Entertainment District. The Perfect Location If Attending The Toronto International Film Festival (TIFF), And Just Steps To Nearby Venues, such as CN Tower, Rogers Centre, Subways, Restaurants, Shopping, Metro Toronto Convention Centre And Lake Ontario. Everything You Will Need To Have An Amazing Stay Is Included. *NOTE There Is No Parking Included. *The Pool & Sundeck Under Construction - Expected To Open June 2026*

Guest suite in Scarborough

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

4.94 out of 5 average rating, 130 reviews

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

Welcome to our brand new, luxury modern suite located in a quiet, family-friendly neighbourhood. Mins to HWY401/DVP, TTC. Featuring: ✓ Luxury Finishes Throughout ✓ Heated Swimming Pool (seasonal April - Oct) ✓ Dedicated Workspace ✓ Washer/Dryer ✓ High-Speed WIFI ✓ Smart TV with Netflix, Prime & sound system ✓ Keyless Entry (24/7 Self Check-In) ✓ Outdoor BBQ, seating and fire table This upscale oasis is truly the perfect space for business travellers, young professionals & couples alike!

4.94 out of 5 average rating, 200 reviews

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

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.

4.79 out of 5 average rating, 42 reviews

Condo in Toronto

“Modern 3BR Condo w/ Free Parking | 1 Min to 401”

Welcome to your home away from home! Enjoy this fully independent, beautifully maintained 3-bedroom condo located just 1 minute from Scarborough Town Centre and right off Highway 401 — perfect for families, business travelers, and vacation guests. 🏡 The Space ✔️ Entire private apartment ✔️ 3 spacious bedrooms with comfortable beds ✔️ Bright living & dining area ✔️ Fully equipped kitchen ✔️ Clean, modern bathrooms ✔️ High-speed WiFi ✔️ Smart TV ✔️ In-unit laundry ✔️ Free parking

5 out of 5 average rating, 104 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

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.

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

4.9 out of 5 average rating, 97 reviews

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 Don Mills

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

Popular amenities for Scarborough rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 82 reviews

An aerial view showcases a spacious retreat surrounded by lush greenery. A sparkling pool is featured alongside a shaded seating area and a gazebo, enhancing the outdoor living experience. The property is framed by trees, providing a sense of privacy and tranquility.

Home in Ajax

Beautiful Cottage in Ajax

5 out of 5 average rating, 9 reviews

Home in Markham

Walk-out Luxury basement with Gym & Theatre

4.93 out of 5 average rating, 15 reviews

Home in Etobicoke

Seraya Wellness Retreat

5 out of 5 average rating, 27 reviews

A refreshing outdoor pool is surrounded by a wooden deck, offering ample lounge chairs for relaxation. Lush greenery frames the area, creating a serene atmosphere. The pool's clear turquoise water invites enjoyment, while the natural landscaping enhances the overall privacy of the space.

Home in North York

Award Winning Luxury Home with Heated Pool + Sauna

5 out of 5 average rating, 5 reviews

Home in Toronto

Toronto Backyard w/ Pool, Hot Tub & Sauna | 4BR

4.89 out of 5 average rating, 64 reviews

A hot tub and swim spa are shown in a well-maintained outdoor area, surrounded by lush green privacy hedges. Nearby, a modern patio seating area features a table and comfortable couches, enhancing the outdoor relaxation space.

Home in The Queensway

private backyard SPA oasis in Toronto

4.91 out of 5 average rating, 332 reviews

An open-concept living area features hardwood floors and exposed brick walls. A spacious bed is complemented by elegant chandeliers, while a white futon is situated nearby. Decorative artwork adorns the walls, and a light-filled kitchen area is visible in the background.

Home in West Queen West

Victorian Charm – Prime FIFA Base in King West

4.9 out of 5 average rating, 42 reviews

A heated pool is surrounded by lush greenery and features a connected Jacuzzi. Lounge chairs are positioned near the pool, along with a gazebo in the background. Two colorful inflatable rings float on the water, and red outdoor chairs are placed nearby for relaxation.

Home in Clarkson

The Serenity Home Pool/Yoga/Game Room by the Lake

Condo rentals with a pool

4.85 out of 5 average rating, 142 reviews

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

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

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.

4.87 out of 5 average rating, 153 reviews

Beautiful Condo Across CN Tower and MTCC

4.95 out of 5 average rating, 149 reviews

A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.

Condo in Fort York

FIFA Fan Zone Pool-Hottub-Free Parking Walk to BMO

4.89 out of 5 average rating, 879 reviews

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

Condo in Humber Bay Shores

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

4.81 out of 5 average rating, 115 reviews

Humber Bay Family Friendly condo w Terrace&Parking

4.87 out of 5 average rating, 149 reviews

A light-colored sofa is positioned in the foreground, adorned with plush, textured pillows. The modern kitchen in the background features white cabinetry, stainless steel appliances, and a central island topped with decorative items, creating a fresh and inviting space.

Condo in Fort York

FIFA Venue|BMO field|Luxury Condo with FreeParking

4.98 out of 5 average rating, 214 reviews

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

Stylish Condo | Walk to BMO Field + Free Parking

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.

4.93 out of 5 average rating, 129 reviews

Charming Condo w Parking, CN Tower View & Pool

Other holiday rentals with a pool

5 out of 5 average rating, 8 reviews

Guest suite in Pickering

Pool Now Open | Executive Suite | 3PM checkout

4.96 out of 5 average rating, 81 reviews

A serene bedroom features a spacious bed adorned with a light blue quilt. Two bedside lamps provide gentle illumination beside the bed, which is positioned against a wall of windows allowing natural light to fill the room. A mirror reflects the calming space.

Condo in Yorkville

Lux amenities/fast WIFI/walking to sub Yorkville

Condo in Discovery District

A bright bedroom is highlighted by floor-to-ceiling windows which offer a view of the city. A queen-sized bed is framed by modern nightstands with lamps, complemented by a yellow throw blanket and plush pillows. Natural light fills the space, creating a cozy ambiance.

4.89 out of 5 average rating, 37 reviews

Pristine 1Bed+Den Condo Mins to World Cup Stadium

4.91 out of 5 average rating, 57 reviews

A modern living area is presented, featuring comfortable seating and a minimalist design. Artwork is displayed on the walls, and a large TV is mounted for entertainment. Natural light illuminates the space, creating an open and inviting atmosphere enhanced by wood flooring and stylish decor.

Condo in Liberty Village

Terrace views of downtown Toronto

4.81 out of 5 average rating, 73 reviews

CN Tower View 4BD Penthouse+Rogers Centre+Parking

5 out of 5 average rating, 5 reviews

Condo in Toronto

Downtown 2BR | CN Tower & Water Views + Parking

Apartment in North Toronto

4.91 out of 5 average rating, 46 reviews

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