Vacation rentals with a pool in Adjala–Tosorontio

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, 413 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.

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, 100 reviews

A spacious balcony features a cozy seating area with a large hanging chair and a fire table surrounded by stylish furnishings. A propane grill is positioned nearby, and warm lights create a soothing ambiance against a twilight backdrop over the water.

Condo in Innisfil

Luxury Beach Spa w/ Private Sauna!

Escape to the Beach at Friday Harbour Resort in our newest addition to our Spa Getaway Group of professionally designed suites that will take you to a luxury destination close to home! This stunning Miami Boho Beach Hotel type vibe suite is very spacious and boasts 3 fire elements (indoor & Out) and your own private in-suite Sauna! With 2 beds and 2 baths there is plenty of space for a couples, friends or family stay! Make memories that last a lifetime in our most unique experience suites!

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.

Apartment 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.

The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.

4.95 out of 5 average rating, 921 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB, SEASONAL POOL 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms Pool closed for the season ** Please note: hot tub is closed from Nov 3rd for approx 2 weeks

4.97 out of 5 average rating, 111 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

4.83 out of 5 average rating, 143 reviews

Guest suite in Minesing

Farmhouse Guest Suite; Year round hot tub

Unique Farmhouse stay in modern Guest Suite Fully stocked kitchenette Bedroom/Livingroom Suite - sleeps 4 Ensuite bathroom with shower Wrap around porch for a glass of wine or your morning coffee. Year round hot tub. Firepit - toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in all months. 1 QUEEN BED 1 QUEEN PULL OUT COUCH Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

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.

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.

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

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

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

4.83 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

4.88 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

4.91 out of 5 average rating, 325 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 Studio in King West – TIFF/FIFA Ready

Condo rentals with a pool

5 out of 5 average rating, 125 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

A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.

4.87 out of 5 average rating, 466 reviews

Base of Blue Mountain, Modern Studio

The open concept living area features a modern sofa and armchair arranged around a glass coffee table. A gas fireplace is centered on the wall beneath a mounted TV. Light streams through large windows, illuminating the space.

4.89 out of 5 average rating, 270 reviews

Hidden Haven - Shuttle to Blue / Private Patio

Condo 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 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!

4.86 out of 5 average rating, 240 reviews

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.

Condo in Mississauga

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

4.91 out of 5 average rating, 153 reviews

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.

Condo in Innisfil

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

4.85 out of 5 average rating, 277 reviews

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.

Condo in Fort York

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

Other vacation 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 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, 179 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

4.94 out of 5 average rating, 52 reviews

An antique cannon is displayed on a grassy area, featuring intricate detailing and large wooden wheels. It rests beside a large rock and is set against a backdrop of lush greenery, including coniferous trees and hosta plants.

Apartment in Caledon

Charming Studio Retreat • Heated Pool Available

4.92 out of 5 average rating, 106 reviews

A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.

Apartment in Mississauga

Condo in Heart of Mississauga

5 out of 5 average rating, 11 reviews

A cozy bedroom is highlighted by a plush bed adorned with soft linens and decorative pillows. A bedside lamp casts a warm glow, while art prints with nature motifs hang above the bed. Nearby, a modern dresser and a comfortable sofa are visible, providing inviting spaces for relaxation.

Condo in Shanty Bay

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

Townhouse in Blue Mountain Resort Area

A spacious living room features large windows allowing natural light to fill the area. Comfortable sofas are arranged around a coffee table, complemented by a soft rug. A fireplace adds warmth, while a large television is mounted above the mantel.

4.99 out of 5 average rating, 149 reviews

Blue Mountain Escape! Pool&HotTub. Walk to Village

4.92 out of 5 average rating, 49 reviews

A modern living space features a sleek television mounted above a stylish wooden media console with drawers. A comfortable chair with a cushion is positioned nearby, complemented by a small potted tree. Natural light fills the area through large windows.

Apartment in Innisfil

Beautiful 2 Bed/2 Bath Condo, Private Balcony