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, 810 reviews

Hot Tub & Cozy 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!

4.95 out of 5 average rating, 184 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.

Flat 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.

4.94 out of 5 average rating, 151 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.

5 out of 5 average rating, 126 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

4.97 out of 5 average rating, 103 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.

4.95 out of 5 average rating, 328 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

4.97 out of 5 average rating, 111 reviews

Home in Alton

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat

Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • 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

4.9 out of 5 average rating, 130 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.

Apartment 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.

4.96 out of 5 average rating, 112 reviews

A modern living area features a spacious sofa arranged around a glass coffee table, with light streaming through large floor-to-ceiling windows. The open layout connects to a dining area with stylish seating and a kitchen, showcasing sleek cabinetry and contemporary appliances.

Loft in Liberty Village

Corner Unit in Liberty Village (Parking + Balcony)

Free parking available+ Close proximity to Budweiser Stage. Located in Liberty Village - one of Toronto’s most sought-after neighborhoods - this corner unit is a place to live, work, & play. The spacious, 700 sq ft layout offers 270-degree views of the city and Lake Ontario. With floor-to-ceiling windows, this 1 Bedroom + Den is flooded with natural light and zero wasted space. Enjoy a morning coffee or watch the sunset over cocktails on either of the two walk-out balconies.

4.96 out of 5 average rating, 136 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.

Guest house 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.

4.82 out of 5 average rating, 194 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.

Flat in Milton

Backyard Oasis Guesthouse.

POOL IS CLOSED TILL MAY 2026 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.

4.98 out of 5 average rating, 164 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.

Popular amenities for Milton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

An open-concept kitchen and living area features light hardwood flooring and contemporary furnishings. A white leather sofa complements a wooden coffee table, while a large kitchen island with bar stools is highlighted. A dining table accommodates six, and colorful tile accents add character to the space.

Home in Burlington

Modern Luxury House w/EV Charger & Heated Pool

Home in Aldershot Central

The indoor pool area is illuminated by natural light from skylights and large windows. A landscaped view can be seen outside, enhancing the serene atmosphere. An HD TV is mounted on the wall, while comfortable seating is arranged beside the pool, creating a cozy environment.

4.75 out of 5 average rating, 65 reviews

Four seasons Pool Retreat near downtown!

4.82 out of 5 average rating, 34 reviews

Home in Hamilton

The Bayfront Flat - Harbour Views + Private Pool!

4.91 out of 5 average rating, 108 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

5 out of 5 average rating, 19 reviews

A private backyard features a sparkling pool surrounded by a spacious patio. A large dining table with bright green chairs is shaded by a vibrant umbrella. Grassy areas and tall trees offer a serene, enclosed atmosphere, enhancing the outdoor living experience.

Home in Erin Mills

Family Oasis with Pool and Hot Tub

4.82 out of 5 average rating, 17 reviews

The open-concept living space features a dining area with a wooden table and four chairs, complemented by a cozy living room furnished with comfortable seating. Large windows allow natural light to illuminate the space, and a wall-mounted television is positioned above a fireplace.

Home in Oakville

Gorgeous Getaway in Oakville

5 out of 5 average rating, 21 reviews

A spacious outdoor area features a heated pool surrounded by a tiled deck. Comfortable seating is arranged under large umbrellas, alongside a dining set and a barbecue grill. Lush greenery and potted plants enhance the relaxing atmosphere of the space.

Home in Cambridge

Under the Whispering Pines

Apartment rentals with a pool

Apartment in North Toronto

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.

4.85 out of 5 average rating, 120 reviews

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

Apartment in Entertainment District

A softly lit bedroom features a spacious bed with a tufted headboard, complemented by white linens and decorative pillows. A bedside table with a lamp sits on one side, while a flat-screen TV is mounted on the wall. Natural light filters through sheer white curtains.

4.82 out of 5 average rating, 112 reviews

Lux Spacious 3 Beds w CN Tower View (Free Parking)

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, 139 reviews

Lux Waterfront Condo Pool Hot Tub Free 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.

4.89 out of 5 average rating, 455 reviews

Lakeside Condo Studio In Downtown Toronto

Apartment in Humber Bay Shores

A modern living area is featured, showcasing a white sofa adorned with colorful pillows. A round coffee table is centered in front of a wall-mounted TV. Large sliding doors open to a balcony, framed by greenery and offering city views.

4.94 out of 5 average rating, 173 reviews

Hidden gem in Humber bay shores Toronto w/ parking

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, 101 reviews

Beautiful Lake View Studio Condo + 1 free Parking

Apartment in Entertainment District

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, 121 reviews

Charming Condo w Parking, CN Tower View & Pool

Other holiday rentals with a pool

4.95 out of 5 average rating, 66 reviews

A modern living area is presented, featuring a large sectional sofa positioned next to a glass coffee table. Floor-to-ceiling windows showcase panoramic views of the city. A 65-inch Smart TV is visible, displaying various streaming options. Natural light fills the room, enhancing the open space.

Apartment in Mississauga

Luxury 2.5Br-2Bath 1 Prk Condo SQ1 Striking Views

4.76 out of 5 average rating, 172 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.

Apartment in Mississauga

Beautiful Condo with Parking Mississauga Downtown

4.87 out of 5 average rating, 38 reviews

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.

Flat in Mississauga

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, 22 reviews

Flat in Cooksville

Stylish 2bed, 2bth Apt. Malls & 25 Mins to Toronto

4.94 out of 5 average rating, 16 reviews

A historic stone house stands amidst lush greenery, featuring large, deep windows and a welcoming entryway framed by vibrant flower pots. The architectural details, including decorative cornices and a pitched roof, highlight its charming character in a serene outdoor setting.

Flat in Guelph-Eramosa

Private 2-bed Apt in Gorgeous Historic Home w/pool

4.95 out of 5 average rating, 96 reviews

A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.

Flat in Caledon

Separate apartment with pool, on golf course.