Vacation rentals with a pool in Caledon

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.96 out of 5 average rating, 411 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.95 out of 5 average rating, 375 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Loft in Niagara-on-the-Lake

A spacious loft area features a cozy sleeping space with a large bed, complemented by a decorative light fixture overhead. A television is positioned for viewing, and natural light fills the area through multiple windows. A comfortable seating area and soft textures contribute to the serene environment.

4.9 out of 5 average rating, 455 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

4.99 out of 5 average rating, 175 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

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, 799 reviews

Cozy Hot Tub & 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, 181 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.

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.

4.95 out of 5 average rating, 326 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!

4.95 out of 5 average rating, 117 reviews

The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.

Condo in Kitchener

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

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

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.

4.82 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.

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.

Popular amenities for Caledon rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Niagara-on-the-Lake

The exterior of a custom-built home is showcased, featuring a black and white facade with multiple gables. Lush greenery surrounds the property, highlighted by colorful autumn foliage from a large tree. A spacious driveway leads to an attached garage.

4.89 out of 5 average rating, 66 reviews

Vineyard Estate by the River with Pool!

4.91 out of 5 average rating, 116 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

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

4.83 out of 5 average rating, 30 reviews

An outdoor area is visible with a private pool surrounded by a spacious patio. Red seating is arranged near the pool, along with a shaded area under an umbrella. The cottage, characterized by a combination of brick and wood siding, is set against a backdrop of lush trees.

Home in Orangeville

Private cottage heated pool/HotTub/Games 20 Acre

4.85 out of 5 average rating, 130 reviews

A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.

Home in Waterloo

Entire Guest Unit+Free Parking by Glenbridge Plaza

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

4.91 out of 5 average rating, 324 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 – TIFF/FIFA Base in King West

Condo rentals with a pool

A modern living area features a light-colored sofa with decorative pillows, accompanied by a clear glass coffee table. A sleek chair is positioned beside the comfortable seating. Large glass doors provide views of the outdoor area, with sleek kitchen cabinetry visible through the open layout.

4.81 out of 5 average rating, 514 reviews

Lovely 2-bedroom at Friday Harbour

4.91 out of 5 average rating, 123 reviews

The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.

Condo in Unionville

Downtown Markham Unionville

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, 137 reviews

Lux Waterfront Condo by Rogers -IndoorPool-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

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

4.87 out of 5 average rating, 168 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Condo in Entertainment District

A balcony offers a view of the Toronto skyline, including several skyscrapers and the iconic CN Tower. A small round table and a chair are positioned near the railing, complementing the modern urban scene against a clear blue sky.

4.83 out of 5 average rating, 240 reviews

⭐️KING Bed Luxury Condo - CN Tower View + Parking⭐️

4.8 out of 5 average rating, 266 reviews

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

An open concept living area is illuminated by city lights, featuring large windows offering views of the CN Tower. A modern sofa sits beside a stylish wooden bar, while a flat-screen television is positioned against a sleek white console. The space is designed for relaxation and entertainment.

4.85 out of 5 average rating, 276 reviews

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Other vacation rentals with a pool

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

Home in Niagara-on-the-Lake

A serene outdoor space is featured, showcasing a well-maintained garden with a large grassy area and elegant stone patio. Wooden decking surrounds a heated spa pool, with stylish seating arrangements and an alfresco dining table set for guests. Soft lighting enhances the tranquil ambiance.

4.97 out of 5 average rating, 38 reviews

Serenity Notl, Lux Home & Spa Pool! 15 m to Falls!

5 out of 5 average rating, 26 reviews

The exterior of the estate features a striking stone facade with large, arched windows that provide ample natural light. A grand entrance is highlighted by a solid black door, flanked by elegant sidelights. The driveway leads to two spacious garage doors below a charming roofline.

Home in Etobicoke

Luxe Haven Heated Pool Sauna Gym

4.91 out of 5 average rating, 80 reviews

A spacious living area features a combination of leather and fabric seating arrangements, with natural light filtering through expansive glass doors. A modern coffee table is centered on a decorative rug, while greenery from indoor plants adds a touch of nature to the decor.

Guest suite in Etobicoke

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

4.84 out of 5 average rating, 77 reviews

The living area is designed with modern furnishings, featuring a gray sofa paired with two bright red chairs. A round coffee table is set with decorative items, including a plant. A painting above the sofa adds a pop of color, while natural light filters through the large windows.

Apartment in Mississauga

Modern 1 Bed Condo Mississauga

Condo in Humber Bay Shores

A bright, open living area features large floor-to-ceiling windows, allowing natural light to illuminate the space. A sleek white sofa is accented with teal cushions, paired with a glossy coffee table. A dining area with beige chairs complements the modern decor, all set against a stylish area rug.

4.95 out of 5 average rating, 20 reviews

Luxury Lakeview Condo free parking Pool Hottub Gym

4.91 out of 5 average rating, 23 reviews

Apartment in Pickering

KING & QUEEN, Royal Design, A+ Private Access

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.