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.

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...

Cleanliness

4.97 out of 5 average rating, 499 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.

5.0 out of 5 average rating, 230 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!

4.99 out of 5 average rating, 231 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.

4.91 out of 5 average rating, 288 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.

4.96 out of 5 average rating, 177 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.94 out of 5 average rating, 179 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.

Condo 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, Limberlost, and Algonquin parks nearby, explore this beautiful part of Ontario!

4.87 out of 5 average rating, 451 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 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.

4.99 out of 5 average rating, 231 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (Open from June 1 to start of Oct) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

4.85 out of 5 average rating, 110 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

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.

Evergreen Studio | King Bed/Pool/Hot Tub/Shuttle

Welcome to Evergreen Studio, a cozy mountain retreat at North Creek Resort featuring a stone fireplace. *King bed *Pull-out sofa *Stone fireplace *SMART TV, Rogers Ignite TV & high-speed Wi-Fi *Equipped kitchen *No traditional oven; stovetop + microwave/convection oven Resort Amenities: *Shuttle Service *Year-round hot tub *Pool (scheduled to close Tues Oct 13, 2026) *Tennis Courts *Ski or hike in/out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.96 out of 5 average rating, 259 reviews

4.94 out of 5 average rating, 153 reviews

An indoor heated pool is featured, surrounded by wooden paneling and large windows that provide natural light. A comfortable seating area is positioned nearby, along with exercise equipment visible in the background. The clean water reflects the light, enhancing the serene ambiance.

Cottage in Baysville

Muskoka Forest Chalet with a Private Indoor Pool

Welcome to the beautiful Muskoka Forest Chalet. Equipped with a private indoor pool, wood burning fireplace, home gym, fully stocked kitchen, theatre room, new modern furnishings and much more. Escape the city life with a one-of-a-kind recently upgraded cottage. Whether you are coming with family or friends, our cottage provides a fun and relaxing experience for every guest. Enjoy activities nearby including ice fishing, hiking, snowmobile trails or shopping and dining

The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.

4.96 out of 5 average rating, 104 reviews

Cozy Residence with Walkout to Courtyard

Experience Lakeside Luxury! Located on the ground floor with walkout access to the courtyard with a pool(closed for the season), hot tub(currently closed for repair) fire pit, and lounge areas. Everything you need is just steps away including Starbucks, LCBO, groceries, fine dining and so much more. Enjoy the live music on the pier, golfing, water activities(seasonal), and special events. Check out the Friday Habour website for a calendar of events throughout the year.

Popular amenities for Georgian Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Blue Mountain Resort Area

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

Hospitality

4.84 out of 5 average rating, 291 reviews

4.98 out of 5 average rating, 252 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

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.

Serene mountainside home with View/Shuttle Bus

4.93 out of 5 average rating, 247 reviews

4.89 out of 5 average rating, 140 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

4.89 out of 5 average rating, 171 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*

4.96 out of 5 average rating, 183 reviews

A sunlit living area is presented with large windows overlooking a snowy landscape. Comfortable seating is arranged around a wooden coffee table. Light walls are complemented by natural wood accents and a colorful rug adds a touch of warmth to the space.

Home in Meaford

Redhill Luxury Home...by the Blue Mountains

4.87 out of 5 average rating, 100 reviews

Home in Feversham

The Castle

Home in Blue Mountain Resort Area

Rivergrass Oasis | Walk to Village & Pool

4.86 out of 5 average rating, 132 reviews

Condo rentals with a pool

4.98 out of 5 average rating, 126 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Condo in Horseshoe Valley

Highland Grand Retreat Studio

4.92 out of 5 average rating, 100 reviews

A cozy living area is presented with two sofas and a fabric armchair, arranged around a wooden coffee table. A gas fireplace sits beneath a wall-mounted television. Large windows allow natural light, offering views of the surrounding landscape.

4.93 out of 5 average rating, 313 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

LocationHot tubCheck-in

Condo 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.

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

LocationFamilyCleanliness

4.99 out of 5 average rating, 134 reviews

4.92 out of 5 average rating, 236 reviews

The Friday Flat | Sunny Escape by the Marina

A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.

4.94 out of 5 average rating, 653 reviews

Blue Vista | Pool/Hot Tub/Shuttle/WalkToBlue

The living room is designed with a cozy sectional sofa and a coffee table placed centrally. A mounted flat-screen TV is positioned above a white-brick fireplace. Natural light filters through sheer curtains, enhancing the welcoming feel of the space.

4.93 out of 5 average rating, 409 reviews

Cozy & Charming Retreat at Blue Mountain

A bright kitchen and dining area feature a modern white countertop with seating, complemented by a wooden table surrounded by dining chairs. Natural light enters through several windows, and a clock adorns the wall, enhancing the space's functionality and warmth.

4.95 out of 5 average rating, 184 reviews

Rustic Chic Renovated 2Bd Condo by Village

Other holiday rentals with a pool

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.

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

4.97 out of 5 average rating, 269 reviews

4.92 out of 5 average rating, 218 reviews

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

Toronto Vacation | ➊ The One Toronto Villa

4.98 out of 5 average rating, 565 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

4.95 out of 5 average rating, 353 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)

4.91 out of 5 average rating, 140 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

Townhouse in Wasaga Beach

An oval-shaped pool is situated just steps from the sandy beach. Surrounding the pool are several lounge chairs and a shaded gazebo. The calm water of the bay is visible in the background, creating a serene setting for relaxation.

Waterfront | Heated Pool, Beachfront, BBQ, AC

4.97 out of 5 average rating, 145 reviews

4.98 out of 5 average rating, 125 reviews

Cottage in Sprucedale

Hot tub! Fall colours! Rare Sum wknd available