Holiday rentals with a pool in Adjala–Tosorontio

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 101 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

Welcome to our exquisite 2BR/2BA oasis, where relaxation knows no bounds. Embrace the tranquility of our inviting space. Indulge in the comforts of home with a fully equipped kitchen, cozy living area and two private bedrooms designed for restful nights. Soak in the hot tub's warmth, swim and lounge by the pool or gather round the fire pit for memorable conversations under the stars. Your perfect vacation retreat awaits. Book now to experience luxury, comfort & outdoor delight like never before!

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

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

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, 412 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...

Guest house 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.

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, 176 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.

4.93 out of 5 average rating, 801 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!

4.95 out of 5 average rating, 327 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!

4.99 out of 5 average rating, 194 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Flat in Newmarket

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

4.85 out of 5 average rating, 390 reviews

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

4.93 out of 5 average rating, 194 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Townhouse in Blue Mountain Resort Area

An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.

4.94 out of 5 average rating, 535 reviews

3BR Sierra Scandi Chic - Closest to Village

Treat yourself to a getaway at our uncluttered, spacious, and fully-equipped 3 bedroom end-unit stacked townhouse at 110 Fairway Court. Just a 5 minute walk from the village and facing the Monterra golf course 1st hole, you’ll enjoy beautiful views of the mountain and easy access to village activities. With over 1,600 square feet of living space and all the comforts of home, our place has everything you need for a relaxing stay. Taxes include 13% HST and 4% municipal accommodation tax

4.97 out of 5 average rating, 110 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

Popular amenities for Adjala–Tosorontio rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 49 reviews

A restored stone farmhouse is framed by lush greenery and colorful flower beds. A well-maintained stone wall borders the property, providing a rustic charm. The approach features a paved path leading up to the welcoming porch, inviting guests to explore the landscaped surroundings.

Home in Mono

Country Family Getaway with Pool and Trails

A spacious bed is adorned with a textured white bedspread and a decorative 'welcome' pillow. Behind the bed, a scenic mural displays misty mountains and lush forests, enhancing the room's atmosphere. Two sleek reading lights are positioned on either side, adding functionality to the space.

4.84 out of 5 average rating, 106 reviews

The Cozy Corner Townhome - Shuttle to the Village

4.88 out of 5 average rating, 250 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

4.9 out of 5 average rating, 77 reviews

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

2 Bd Boardwalk Condo Patio Oasis

The living area features large windows allowing natural light to illuminate the space. A modern sectional sofa with colorful pillows and a decorative throw faces a sleek coffee table. A cozy fireplace is positioned beneath a wall-mounted TV, creating a warm environment.

4.87 out of 5 average rating, 127 reviews

Blue Mountain Retreat In Historic Snowbridge

4.99 out of 5 average rating, 160 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

A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.

4.93 out of 5 average rating, 215 reviews

Serene mountainside home with View/Shuttle Bus

4.88 out of 5 average rating, 207 reviews

The kitchen features an open layout with warm wood flooring and a large dining table set for twelve. Natural light enters through two windows beside the door. Stainless steel appliances and a well-equipped countertop complete the functional space.

Home in Kimberley

Heart of Kimberley - with views and a hot tub

Apartment rentals with a pool

A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.98 out of 5 average rating, 180 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

5 out of 5 average rating, 124 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

A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.

4.97 out of 5 average rating, 110 reviews

3 Peaks at Blue Mountains, your luxury staycation!

The open-concept living area features two comfortable sofas with decorative cushions. A dining table is set for six nearby, while kitchen access is visible in the background. Natural light enters from large windows, with wooden accents enhancing the space.

4.87 out of 5 average rating, 146 reviews

Out of the Blue - Shuttle to Blue, Walk & Trails!

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, 170 reviews

Hidden gem in Humber bay shores Toronto w/ parking

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.

4.91 out of 5 average rating, 153 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

A modern kitchen area is showcased featuring sleek white cabinetry and stainless steel appliances. A stone countertop provides space for meal preparation, complemented by four red stools. A bowl of green apples adds a fresh touch to the dining area, enhancing the inviting ambiance.

4.9 out of 5 average rating, 558 reviews

Blue Mountain Studio with Summer Pool

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.

4.94 out of 5 average rating, 131 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

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.

Flat in King City

The King's Rest

Townhouse in Blue Mountain Resort Area

A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.

4.96 out of 5 average rating, 222 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Flat in Blue Mountain Resort Area

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

4.99 out of 5 average rating, 178 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

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.

Guest house in Brampton

Bright and Airy Guest Suite with Pool

4.67 out of 5 average rating, 30 reviews

A round wood sauna features wooden benches arranged alongside a central heater. The outdoor deck displays a swim spa surrounded by lounge chairs, with a view of the spacious backyard. An indoor living area showcases a stone fireplace and modern furnishings, while a well-equipped kitchen includes a central island.

Home in Mono

Luxury Hockley Estate Spa

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

4.92 out of 5 average rating, 131 reviews

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Flat in Innisfil

Modern Condo at Friday harbour/Pet Friendly