Holiday rentals with a pool in Georgian Bay

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, 476 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.

4.96 out of 5 average rating, 387 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.

Townhouse in Blue Mountain Resort Area

A clear, inviting outdoor pool is surrounded by landscaped greenery and stone seating areas. The pool features a curved shape with steps leading in, and two poolside lounge chairs are visible. Mature trees provide shade in the background, enhancing the serene environment.

4.96 out of 5 average rating, 358 reviews

Walk 2 Village, Great Kitchen & Beds, Summer Pool!

You will love our renovated condo with quality mattresses, well stocked kitchen, great bathrooms, on demand hot water & walk out rear patio with BBQ and yard access. Heated outdoor pool in complex July/Aug Trust our 350+ reviews telling stories of amazing stays & memories made! The short 5 minute stroll to the village is something you will be sure to enjoy! NETFLIX, cable & unlimited WIFI, cozy gas fireplace, quality towels/ linens + games/ Legos...message us with any questions or to book now.

4.98 out of 5 average rating, 246 reviews

The entrance showcases intricate woodwork and architectural details, with a grand staircase leading to the upper level. A large door opens to the outside, and a vintage chandelier illuminates the inviting foyer, highlighting the craftsmanship of the historic home.

Home in Owen Sound

Butchart Estate: Breathtaking Victorian mansion

Give them a holiday to remember. Gather family or friends and settle in to our beautiful and well-equipped heritage home for a few days. Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, binge some Netflix, or play board games galore. Outdoors, we're famous for our hills, forests, lakes and rivers, the Bruce Trail, and the views out to Georgian Bay. But don't miss the music, museums, the markets, and amazing foodie scene, steps from your door.

5 out of 5 average rating, 215 reviews

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.

Apartment in Innisfil

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!

4.9 out of 5 average rating, 269 reviews

Cottage in Innisfil

Utopia villa and spa

Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

4.99 out of 5 average rating, 214 reviews

Townhouse in Port Severn

Pool, Wifi, Free parking, Golf, Laundry, BBQ

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

4.86 out of 5 average rating, 430 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.

Superhost

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in Toronto

4.93 out of 5 average rating, 204 reviews

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

4.94 out of 5 average rating, 161 reviews

A serene balcony overlooks a sparkling lake, surrounded by lush greenery and distant rolling hills. A single adirondack chair is positioned on the wooden deck, inviting relaxation and enjoyment of the peaceful view.

Apartment in Huntsville

Your Home Away from Home in Beautiful Huntsville!

Take some time away at this Hidden Valley Hideaway in Huntsville, in Muskoka. Located at the Hidden Valley Resort, next to Deerhurst, this 2-bedroom condominium is perfectly located for all seasons. Winter: Enjoy downhill and cross-country skiing, snowmobile trails, and skating all at your doorstep. Spring/Summer/Fall: Enjoy the beach, water sports, golf, treetop trekking, and so much more. With Arrowhead and Algonquin parks nearby, explore this beautiful part of Ontario!

Apartment in Horseshoe Valley

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

4.99 out of 5 average rating, 115 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Welcome to our cozy, modern condo in Horseshoe Valley — the perfect destination for families and groups of friends seeking adventure, relaxation, and unforgettable memories. Just a 2-hour drive from Toronto, our condo offers a prime location to experience it all. Whether you're hitting the slopes, unwinding at the Nordic spa, or exploring the outdoors with mountain biking, golf and tree-top trekking, you'll find everything you need for a perfect getaway.

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, 989 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 projected to open Monday June 15th 2026

Popular amenities for Georgian Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Blue Mountain Resort Area

4.86 out of 5 average rating, 277 reviews

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

4.88 out of 5 average rating, 108 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

Home in Blue Mountain Resort Area

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.

4.88 out of 5 average rating, 141 reviews

Blue Mtn Retreat w Summer Pool, XBox, Free Shuttle

4.94 out of 5 average rating, 238 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

4.92 out of 5 average rating, 132 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

Home in Blue Mountain Resort Area

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.

4.94 out of 5 average rating, 237 reviews

Serene mountainside home with View/Shuttle Bus

4.91 out of 5 average rating, 114 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

4.9 out of 5 average rating, 162 reviews

A cozy bedroom features a spacious bed adorned with a white and blue floral duvet. Warm lighting is provided by bedside lamps on either side of the bed. A tasteful horse artwork is displayed on the wall, complementing the calming blue walls.

Home in Chatsworth

Stonehaven - large country retreat, with pool*

Apartment rentals with a pool

An open-concept living area showcases a modern kitchen with stainless steel appliances and a large island. A cozy seating area features a dark sofa and an armchair, positioned near a stone fireplace. Natural light fills the space through multiple windows.

4.92 out of 5 average rating, 193 reviews

Blue Mountain condo in Historic Snowbridge

An open-concept living area features large windows allowing natural light to fill the space. Comfortable sofas are arranged around a central coffee table, and a mounted television is positioned above a sleek fireplace. Soft tones and textures contribute to a relaxing atmosphere.

4.9 out of 5 average rating, 111 reviews

Sunny Days | Steps to Blue Mtn | Pool & Shuttle

4.88 out of 5 average rating, 121 reviews

A bright living area features a comfortable gray sectional sofa with yellow accent pillows. A round coffee table sits in front, while large windows allow natural light to fill the space. A ceiling fan hangs overhead, and a piece of wall art adds a touch of color.

Apartment in Huntsville

Huntsville Lakeside Ski Chalet

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

4.93 out of 5 average rating, 326 reviews

Cozy Studio Mountainside stay in Blue Mountains

4.87 out of 5 average rating, 305 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

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, 116 reviews

3 Peaks at Blue Mountains, your luxury staycation!

Apartment in Horseshoe Valley

The living area features a modern design with a large flat-screen TV mounted above a stone fireplace. A cozy gray sofa is paired with a rustic coffee table and a comfortable orange armchair. Natural light enters through double glass doors leading outside.

4.98 out of 5 average rating, 116 reviews

Resort Condo (2 suites) near Horseshoe Valley

4.99 out of 5 average rating, 111 reviews

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.

Apartment in Innisfil

Bohemian Luxury at Friday Harbour Resort Simcoe

Other holiday rentals with a pool

4.93 out of 5 average rating, 129 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

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, 255 reviews

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

4.99 out of 5 average rating, 149 reviews

A spacious outdoor area features a picnic table and multiple lounge chairs arranged on well-maintained grass. The wooden structure in the background has large windows, adorned with awnings, and is surrounded by greenery under a clear blue sky.

Farm stay in Markdale

Experience Country Living at Firefly Ridge

Superhost

The modern building exterior features large windows that allow natural light to fill the space. A sleek front door is framed by a geometric overhang. The driveway accommodates several vehicles, and a vibrant red car is parked in the foreground.

Flat in Toronto

4.87 out of 5 average rating, 102 reviews

Charming and Luxurious 2BR+1Bath Guest Suite

Cottage in Victoria Harbour

A spacious wooden deck surrounds a heated above-ground pool, providing a refreshing blue oasis. Surrounding greenery offers privacy and a sense of seclusion, with patio furniture positioned for relaxation. Umbrellas are situated for shade, inviting guests to enjoy outdoor leisure.

4.94 out of 5 average rating, 83 reviews

Gorgeous Winfield Chalet Cottage

4.96 out of 5 average rating, 27 reviews

A vibrant, triangular-shaped house is surrounded by greenery, reflecting in a clear, inviting swimming pool. A shaded seating area with lounge chairs can be seen beside the pool, and large glass doors allow natural light to fill the interior space.

Home in Elora-Salem

Riverside Retreat w Hot Tub, Pool & Sauna in Elora

Bungalow in Lafontaine Beach

The cottage features a welcoming porch with large windows, providing a view of the surrounding trees and nature. The entrance is flanked by picnic tables, inviting outdoor gatherings. Soft evening light enhances the cozy atmosphere of the renovated exterior.

4.91 out of 5 average rating, 75 reviews

Sweet Memories of Georgian Bay