Vacation rentals with a pool in South Bruce Peninsula

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.

4.97 out of 5 average rating, 232 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *Shuttle Service *Year Round Hot Tub *Pool (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

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.

4.96 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.

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*

Situated on 100 acres of grass, field and forest, this easy-access property has miles of trails, in-ground pool (not heated), huge lawns, beach volleyball, fire pit, tubing run, and lots of space indoors - 5 rooms on the main level, 6 bedrooms upstairs. >> Borders OFSC trail Ideal for multi-family groups looking for a great country getaway, it is one minute from the major highways coming from Toronto & Guelph towards Owen Sound. We offer full-week discounts. (Please note firm pool closing dates)

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.

4.97 out of 5 average rating, 176 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

This eco friendly house of 4,500 sq ft is bright, modern, luxurious on 50 acres of rolling hills with a beautiful pond and hiking trails. All bedroom ensuite plus 2 extra full bathrooms. Comfortably sleeps up to 24 guests. Amazing view, sunset and star gazing. Salt water pool in the summer. Outdoor BBQ, fire pit, Hot Tub April to Nov. Minutes to Christie beach, ski hills, golf courses, Bruce Trail. Enjoy snowshoeing, cross country. Serenity on top of the hill! See more info under the space.

4.95 out of 5 average rating, 342 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!

4.86 out of 5 average rating, 429 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.

Apartment in Blue Mountain Resort Area

The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.

4.96 out of 5 average rating, 380 reviews

Studio at Blue-KingBed/Pool/HotTub/Shuttle

Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Pool (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

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

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. PLEASE NOTE DOGS MUST BE ON A LEASH WHILE ON THE PROPERTY.

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.

4.93 out of 5 average rating, 626 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB & SEASONAL POOL 360 degree views! We are a 3-5 minute walk to the Village with stunning views of the golf course and mountain! Perfect place to relax on the balcony or couch after a busy day of soaking up all Blue has to offer! ★Self-Check In ★Equipped kitchen, towels & linens ★ SMART TV, WIFI & CABLE ★ Games, high chair, PackNPlay ★ Resort hot tub with indoor changeroom and washrooms ★ Pool expected to open the week of June 1 2026

4.93 out of 5 average rating, 129 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

Private heated pool + year-round hot tub on a secluded 5-acre mountain retreat. Sleeps 10 (max 8 adults) with total privacy. Perfect for ski days and starry-night soaks! Ski Ontario’s best hills by day, then unwind in the year-round hot tub under the stars. Enjoy a private 500ft mountain for sledding, cozy fireplace nights, open-concept living and much more. ✔ Heated Pool (Seasonal) ✔ Hot Tub ✔ Private Sledding Hill ✔ Minutes to Blue Mountain

4.88 out of 5 average rating, 208 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

Welcome to the hamlet of Kimberley nestled in the Beaver Valley. Surrounded by nature, the Rock House is a historic six bedroom century home with beautiful views close to many outdoor activities, and located beside an unassuming gourmet restaurant and a general store with fresh coffee and in-house sourdough bread. We are located 25 minutes from Blue Mountain and 2 minutes from Beaver Valley Ski Club.

Popular amenities for South Bruce Peninsula rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 17 reviews

A spacious and modern home is set on a hillside, surrounded by vibrant autumn foliage. The structure features a striking red roof, a well-maintained landscape with stone pathways, and large windows that reflect the surrounding nature.

Home in Nottawa

Nature Retreat in The Pretty River Valley for 6

5 out of 5 average rating, 14 reviews

Home in Palgrave

Relaxing Luxury Palgrave Cottage w/pool on 3 acres

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, 116 reviews

Cozy Corner Townhome | Shuttle + Patio + Pool

4.86 out of 5 average rating, 276 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.

4.88 out of 5 average rating, 141 reviews

Blue Mtn Retreat w Summer Pool, XBox, Free Shuttle

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

The exterior of the town-home is showcased, featuring a combination of stone and blue siding. Neatly manicured lawns surround the property, and several large windows allow natural light to illuminate the interior. A small tree is planted in the foreground, adding a touch of greenery.

4.85 out of 5 average rating, 119 reviews

Blue Mountain Village Townhome 4 Bedroom w Shuttle

4.87 out of 5 average rating, 101 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

Condo rentals with a pool

The kitchen displays modern appliances, including a refrigerator, microwave, and stove, set against a stylish backsplash. A granite countertop extends into a small dining area with two black stools, while light fixtures offer bright illumination in the space.

4.81 out of 5 average rating, 220 reviews

Blue Mountain Escape, WIFI, Base of North lift

4.88 out of 5 average rating, 524 reviews

Enjoy the Return of Spring at Blue Mountain

A bright living room is displayed with a gas fireplace and comfortable seating arranged around a circular coffee table. Large windows allow natural light to fill the space, while a cozy area rug adds texture. Decorative wall art enhances the inviting ambiance.

4.81 out of 5 average rating, 129 reviews

Clearview Chalet • Modern 3BR • Mountain Stay

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!

An open-concept living area is showcased, featuring a cozy sectional sofa and a stone fireplace with a modern TV mounted above. Natural light streams through large windows, illuminating the earthy tones of the decor. A circular wooden coffee table with decorative elements completes the inviting space.

4.92 out of 5 average rating, 153 reviews

Highlands Lodge & Loft - Shuttle & Outdoor Pool

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, 294 reviews

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

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, 175 reviews

Rustic Chic Renovated 2Bd Condo by Village

The studio features a spacious bed adorned with white linens, flanked by two wall-mounted lights casting a serene glow. A mountain-themed mural in shades of teal and blue creates a calming backdrop, while a small table and a white dresser provide functional accents.

4.84 out of 5 average rating, 702 reviews

Creekside Smart Studio at Blue Mountain

Other vacation rentals with a pool

Townhouse in Blue Mountain Resort Area

Two comfortable sofas with decorative pillows are positioned around a dark coffee table in a spacious living area. A minimalist art piece adorns one wall, while a staircase leads to the upper level. The modern kitchen is visible in the background.

4.89 out of 5 average rating, 179 reviews

The Snowbridge Lookout on Monterra Golf Course

5 out of 5 average rating, 6 reviews

An aerial view of the surrounding area highlights the proximity of the Black Horse Motor Inn to the beach. The site features green trees, various cottages, and a heated saltwater pool, with the shoreline visible in the distance.

Cabin in Sauble Beach

Tiny Luxury Cottage - Cottage 1

4.81 out of 5 average rating, 70 reviews

The tiny house exterior features a neutral color palette with a wooden porch area. A welcoming sign displays 'Honey House.' The window allows natural light in, while a small grill is positioned nearby, surrounded by greenery and a well-maintained lawn.

Tiny home in Wiarton

Welcome to the Tiny Honey House!

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, 868 reviews

Headwaters Retreat - Hot Tub Summer Getaway

Loft in Blue Mountain Resort Area

A well-appointed bedroom features a spacious bed dressed in a white coverlet, flanked by two bedside tables with blue lamps. Neatly arranged towels are stacked on the bed, and warm, muted tones create a calming atmosphere.

4.83 out of 5 average rating, 202 reviews

Home Away From Home at Blue - Renovated Clean Loft

Guest suite in Orangeville

A serene winter scene captures a snowy landscape framed by tall evergreen trees. A clear blue sky contrasts with the bright white snow covering the ground and adjacent areas. The pathway leads towards a structure partly obscured by the snow-laden trees, suggesting a peaceful retreat.

4.96 out of 5 average rating, 176 reviews

Your Peaceful Santuary in Nature

Chalet in Blue Mountain Resort Area

A bright bedroom features a spacious bed covered with soft linens and a textured throw. The walls are painted blue, complemented by decorative curtains. A piece of artwork depicting a deer is displayed above the bed, and a bedside lamp is positioned on a small white table.

4.97 out of 5 average rating, 329 reviews

The Little Blue Spruce! Free shuttle to village