Holiday rentals with a pool in Brampton

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

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

Fully renovated 2 bedroom walkout basement modern suite(1,100 sqft), increased in size windows, feels like ground floor, 20x30 swimming pool. 3 minutes to UTM. This home is in a quiet, peaceful neighborhood that offers access to scenic walks and parks nearby. 2 minutes to HWY. DWTN Toronto and DWTN Mississauga is close which makes dining at great restaurants, browsing boutique shops, shopping malls and general sightseeing both easy and convenient. Pool/seasonal/notHeated LICENSE# 2022-000188-STA

LocationValueAir conditioning

4.92 out of 5 average rating, 198 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Flat in Mississauga

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

ValueFamilyCheckout

4.99 out of 5 average rating, 169 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.

Apartment 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

LocationValueLaundry

Guest suite in Mississauga

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

FamilyValueCheckout

4.92 out of 5 average rating, 174 reviews

4.82 out of 5 average rating, 11 reviews

Home in Brampton

Heated Pool Estate by Canterra Stays · Sleeps 20

✨ The estate your family reunion has been waiting for. Twenty of you across three private living spaces — the main home, a lower-level 2-bedroom + den suite, and an above-garage coach suite with its own kitchen — wrapped around a heated pool, a covered gazebo lounge, and a BBQ that runs all evening. Guests put it best: adults and kids super happy, most of the trip spent right here. Ten beds, 4.5 baths, EV charging, minutes to Pearson. One booking. Total privacy. The summer everyone remembers.

FamilyLocationSleep quality

Guest house in Mississauga

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.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, 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. IMPORTANT: You MUST read “Other Details To Note”

ValueLocationAmenities

4.89 out of 5 average rating, 116 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

4.9 out of 5 average rating, 170 reviews

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

ValueLocationAccess

5.0 out of 5 average rating, 126 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.

Guest house 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.

FamilyValueLong stay

4.92 out of 5 average rating, 184 reviews

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!

LocationValueAir conditioning

4.76 out of 5 average rating, 119 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

LocationValueAccess

5.0 out of 5 average rating, 4 reviews

Sunset Retreat | 2BR/2BA | CN Tower View + Parking

Welcome to your modern 2-bedroom, 2-bathroom urban retreat in the heart of Mississauga. Perched high above the city, this beautifully appointed condo offers stunning panoramic views, breathtaking sunsets, and views of the CN Tower and Toronto skyline. Whether you're visiting for business, vacation, or an extended stay, you'll enjoy a thoughtfully designed space with everything you need for a relaxing stay.

FamilyValueAccess

A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.

4.85 out of 5 average rating, 276 reviews

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

LocationFamilyBathroom

Popular amenities for Brampton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 107 reviews

A swimming pool is featured in a serene outdoor space, surrounded by lush greenery and tall trees. The circular pool is complemented by a stone wall background. A shaded seating area with a table and chairs is nearby, promoting relaxation and enjoyment.

Home in Don Mills

Casa Meya – Toronto Poolhouse Villa

LocationFamilyBack garden

4.86 out of 5 average rating, 111 reviews

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

Toronto Pool Retreat

LocationValueKitchen

4.91 out of 5 average rating, 348 reviews

Home in Niagara

King West Victorian Gem Downtown - Walk Everywhere

LocationValueKitchen

5.0 out of 5 average rating, 25 reviews

Home in Brampton

Zen Oasis: Pool, Koi-Pond, Pool Table | 20 min YYZ

LocationFamilyPool

4.96 out of 5 average rating, 25 reviews

Home in Cheltenham

Indoor Pool & Hot Tub Villa | Sleeps 14

LocationFamilyAccess

4.85 out of 5 average rating, 52 reviews

A modern house exterior is displayed, featuring a well-maintained lawn and landscaped garden. The driveway is paved with gravel and concrete, leading to a covered porch area. Large windows provide an inviting entrance, while shaded trees contribute to a pleasant outdoor setting.

Home in Mississauga

Comfortable &Stylish 4BD Stay Near Toronto Airport

FamilyLocationBathroom

4.93 out of 5 average rating, 74 reviews

A modern luxury home is displayed with a contemporary stone facade and wooden accents. The upper balcony features a glass railing, and a well-kept lawn enhances the inviting exterior. The driveway leads to a double garage with stylish doors.

Home in North Etobicoke

Beautiful Oasis In the city with Heated Pool

ValueFamilyAccess

4.81 out of 5 average rating, 31 reviews

Home in Brampton

Poolside Escape | Pool + Hot Tub + Private Lot

LocationFamilyHospitality

Apartment rentals with a pool

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

4.86 out of 5 average rating, 219 reviews

Beautiful Penthouse with Breathtaking View

LocationFamilyAir conditioning

4.94 out of 5 average rating, 172 reviews

Luxury 2BR Condo w/ Skyline Views & Balcony

ValueFamilyCleanliness

4.98 out of 5 average rating, 130 reviews

Luxury Downtown Condo For 6 (CN Tower View)

FamilyLocationAccuracy

A living area features two brown leather sofas positioned near large windows, offering a view of the downtown skyline. A floor lamp stands beside a decorative bench, and two floral paintings adorn the wall, adding a touch of elegance to the modern space.

4.96 out of 5 average rating, 102 reviews

Prime location • Amazing views • FREE parking

FamilyLocationPets

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.

4.94 out of 5 average rating, 130 reviews

Luxury Downtown Condo For 4 (CN Tower Views)

ValueLocationCondition

The image captures a vibrant urban landscape featuring a modern building with glass and metal elements. The prominent CN Tower stands in the background against a clear blue sky. The area is filled with pedestrians enjoying the surroundings, complemented by greenery and architectural structures.

4.85 out of 5 average rating, 106 reviews

Central downtown condo next2 CNtower+free parking

FamilyLocationOutdoor spaces

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.

4.97 out of 5 average rating, 192 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

ValueFamilyIndoor spaces

A balcony view captures the iconic CN Tower alongside a modern building structure. The expansive glass windows reflect the urban skyline and lake in the distance, evoking a sense of openness and connection to the city.

4.85 out of 5 average rating, 206 reviews

Toronto CN Tower 2 Bed 2 B w Master King w Parking

LocationValueCleanliness

Other holiday rentals with a pool

4.98 out of 5 average rating, 49 reviews

A modern living area features a sectional sofa facing a geometric patterned rug. A dining set and bar stools complement the space. The kitchen is visible, showcasing wood cabinetry and stainless steel appliances. Large windows allow natural light to fill the room, with access to an outdoor balcony.

Flat in Mississauga

Luxury Penthouse Suite SQ1

FamilyValueParking

Apartment in Mimico-Queensway

A bright living area features a soft sofa and a low coffee table, with a large TV mounted on the wall. Floor-to-ceiling windows provide expansive views of the cityscape, while natural light illuminates the space. A transition to the sleeping area is visible in the background.

Stunning Toronto view! Guest Favourite w/ parking!

LocationFamilyComfort

4.9 out of 5 average rating, 83 reviews

4.72 out of 5 average rating, 50 reviews

Flat in Mississauga

Modern Luxe Living – Walk to Square One & Transit

FamilyValueHospitality

5.0 out of 5 average rating, 12 reviews

Flat in Toronto

1 Bedroom-King bed with parking steps to the lake

LocationSolo travelAccuracy

A modern living room features a large sectional sofa with a sleek design, positioned near a floor-to-ceiling window. A flat-screen TV is placed on a low coffee table, while natural light fills the space, highlighting the surrounding urban landscape.

4.83 out of 5 average rating, 78 reviews

Mississauga Square One Condo

FamilyValueLong stay

Guest suite in North Etobicoke

Private 1 bed/1.5 bath in-law suite in a house!

ValueFamilyBiking

4.93 out of 5 average rating, 95 reviews

5.0 out of 5 average rating, 13 reviews

Sky High Luxe Stay | SQ1 | LakeView | Gym Pool Pkg

FamilyLocationView