Holiday rentals with a pool in Milton

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.92 out of 5 average rating, 798 reviews

Cozy HotTub & Fireplace - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

4.96 out of 5 average rating, 180 reviews

A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.

Apartment in Ariss

Rural Retreat, near to Elora

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

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.

4.94 out of 5 average rating, 144 reviews

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.

5 out of 5 average rating, 122 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

4.97 out of 5 average rating, 102 reviews

Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.

Farm stay in Caledonia

Alpaca farm stay and bunkie getaway.

A farm stay on your way to soaking up all that our county has to offer. The bunkie is located next to a restored century barn and an outdoor pool. The property is home to 5 alpacas, mini goats, chickens and our family dog. The bunkie is on a shared property with our home. It's 1 hour from Toronto, 20 minutes from Hamilton, 1-hour from Niagara-on-the-lake and 10 minutes from the historic Ancaster village. Antiquing, hiking, nature tours, golfing, wine tours, farmers markets and more close by.

4.9 out of 5 average rating, 128 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.

Condo in Mississauga

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.

4.97 out of 5 average rating, 109 reviews

Home in Alton

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

5 out of 5 average rating, 78 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.

4.96 out of 5 average rating, 134 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

4.98 out of 5 average rating, 159 reviews

The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.

Cabin in Hamilton

The Fox's Retreat - A Cozy Cabin for Two

Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.

4.84 out of 5 average rating, 288 reviews

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

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.

4.82 out of 5 average rating, 192 reviews

A backyard oasis features a sun-drenched inground pool surrounded by lush perennial gardens. A stone patio is equipped with shaded lounge areas and outdoor seating, creating an inviting space for relaxation. The two-story house overlooks the pool, complementing the tranquil environment.

Apartment in Milton

Backyard Oasis Guesthouse.

Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

Popular amenities for Milton rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 38 reviews

A heated swimming pool is nestled in a lush backyard, surrounded by vibrant greenery and mature trees. The pool features a diving board and is set against a backdrop of colorful plants, creating a serene outdoor retreat.

Home in Mississauga

Luxury House with a Bright Sunroom & a heated pool

5 out of 5 average rating, 19 reviews

The heated saltwater pool is surrounded by a wooden fence, with lounge chairs and an umbrella positioned nearby. A Canadian flag is visible, and the clear blue water reflects the greenery of the trees above, creating a serene outdoor environment.

Home in Burlington

Modern Luxury House w/EV Charger & Heated Pool

4.99 out of 5 average rating, 159 reviews

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

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

5 out of 5 average rating, 12 reviews

An outdoor space features a spa-inspired pool with connected Jacuzzi, surrounded by lounge chairs and an umbrella. A large gazebo housing a dining area is visible, along with landscaped greenery and a clear blue sky enhancing the serene environment.

Home in Bathurst Manor

Luxury Spa Escape with Pool & Jacuzzi

4.79 out of 5 average rating, 29 reviews

Home in Hamilton

The Bayfront Flat - Harbour Views + Private Pool!

4.77 out of 5 average rating, 118 reviews

Home in Oakville

Cozy Retreat in Oakville

4.9 out of 5 average rating, 105 reviews

A spacious living area is highlighted by a light-colored sectional couch, complemented by decorative cushions. A coffee table with a sailboat decor piece sits in the center. The open layout connects to a modern kitchen, featuring sleek appliances and bright lighting.

Home in Hamilton Beach

The Nautical Nook | Luxury Beach House

4.8 out of 5 average rating, 112 reviews

The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.

Home in Stoney Creek

California Chic +Breathe +Unwind +Restore

Condo rentals with a pool

4.85 out of 5 average rating, 119 reviews

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

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

Condo in Entertainment District

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.

4.88 out of 5 average rating, 128 reviews

Beautiful Condo Across CN Tower and MTCC

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.

4.97 out of 5 average rating, 135 reviews

Lux Waterfront Condo by Rogers -IndoorPool-Parking

A contemporary waterfront condominium complex is visible, showcasing multiple glass-fronted balconies and lush greenery surrounding the entrance. The building features an urban design with large windows, allowing for abundant natural light, under a vibrant blue sky with scattered clouds.

4.9 out of 5 average rating, 451 reviews

Lakeside Condo Studio In Downtown Toronto

Condo in Entertainment District

A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.

4.97 out of 5 average rating, 258 reviews

Chic, High-Rise Apartment with CN Tower Views

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.

4.98 out of 5 average rating, 210 reviews

Stylish Downtown Toronto Condo with Free Parking

A desk with an ergonomic chair is positioned near floor-to-ceiling windows, offering a stunning view of Lake Ontario at sunset. The scene features a vibrant sky with hues of orange and purple, along with glimpses of the surrounding greenery and cityscape.

4.98 out of 5 average rating, 100 reviews

Beautiful Lake View Studio Condo + 1 free Parking

4.8 out of 5 average rating, 265 reviews

Stylish 1+1 Corner Suite |Steps to Lake&Downtown

Other holiday rentals with a pool

5 out of 5 average rating, 17 reviews

The spacious bedroom is designed with light neutral tones, featuring a large bed with layered bedding. Soft warm lighting is provided by a stylish chandelier. A comfortable seating area with modern chairs and a decorative table complements the room, along with a large window surrounded by elegant drapes.

Apartment in King City

The King's Rest

Apartment in Etobicoke West Mall

A cozy living area features a comfortable sofa accompanied by a stylish side table and ottoman. A large television is positioned on a wooden console. Natural light filters through the sliding glass doors, which open to a balcony adorned with greenery.

4.96 out of 5 average rating, 48 reviews

Pet Friendly Condo, Private Terrace, Pool & Gym

Place to stay in Etobicoke

A welcoming entryway features a stone staircase leading to a pair of wooden double doors. Flanking the entrance, potted plants add greenery, while large windows provide views of the surrounding yard. The roof is tiled, and a well-maintained lawn adds to the home's appeal.

4.93 out of 5 average rating, 76 reviews

The Snug Oasis - Burrow (Near Airport)

4.76 out of 5 average rating, 169 reviews

The exterior of a modern high-rise building is depicted, featuring an array of floor-to-ceiling glass windows and curved balconies. The structure showcases a sleek architectural design and is surrounded by other tall buildings under a partly cloudy sky.

Condo in Mississauga

Beautiful Condo with Parking Mississauga Downtown

The modern high-rise building features numerous balconies and large windows, creating a sleek façade. Lush greenery surrounds the base, while the blue sky and clouds provide a scenic backdrop, emphasizing the tower's height and contemporary design.

4.87 out of 5 average rating, 38 reviews

City Centre Lodge ( Downtown)

4.96 out of 5 average rating, 73 reviews

The cabin, crafted from natural wood, is surrounded by lush greenery and tall trees. Its entrance features a welcoming front door with large windows, allowing natural light to enter. The rustic design integrates harmoniously with the forested environment.

Tiny home in Milton

The Portal, An Off Grid Cabin in the Tree of Peace

5 out of 5 average rating, 6 reviews

Luxury Condo | SQ1 | Stunning Views | Spacious

The bedroom features a spacious bed adorned with a neutral-toned quilt and decorative pillows. A round gold wall accent adds a touch of elegance. Large windows provide views of the city skyline, while soft lighting enhances the calming atmosphere.