Holiday rentals with a pool in South Bruce Peninsula

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Bruce Peninsula

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 363 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 favourite

Home in Chatsworth

4.89 out of 5 average rating, 152 reviews

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)

Top Guest favourite

Home in Owen Sound

4.98 out of 5 average rating, 232 reviews

The Butchart Estate: your perfect family retreat!

Give them a holiday to remember. With fresh air & freshwater beaches. Escarpment views, grottos & waterfalls. It's a great time to get yourself a little more Canada in beautiful Grey-Bruce. Settle in to our beautiful and well-equipped heritage home. Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, play board games galore. Outdoors, we're famous for our hills, forests, lakes and rivers. But don't miss the music, museums, and amazing foodie scene.

Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 774 reviews

HotTub & Pool Getaway - 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!

Top Guest favourite

Home in Meaford

4.96 out of 5 average rating, 169 reviews

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 two 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 year round. 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.

Guest favourite

Tiny home in Meaford

4.87 out of 5 average rating, 363 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. 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. INTERNET just upgraded! Window Aircon/pool opens end of May or June.

Guest favourite

Cottage in Tiny

4.98 out of 5 average rating, 120 reviews

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.

Top Guest favourite

Cabin in Mono

4.95 out of 5 average rating, 316 reviews

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!

Guest favourite

Cottage in Meaford

4.93 out of 5 average rating, 105 reviews

Woodski Retreat w/Heated Pool on 3+ Private Acres

This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

Top Guest favourite

Apartment in The Blue Mountains

4.99 out of 5 average rating, 142 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 * New Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convectional oven combo along with a stove top *Shuttle Service *2 Year Round Hot Tubs *Seasonal Pool (open as of May 31st 2025) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Top Guest favourite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 230 reviews

The White Cedar Chalet! pool + free shuttle

The White Cedar Chalet For your perfect family vacation in Blue Fully stocked kitchen with lots of extras provided 🫖☕️🫙🍽🥂 🛌 5 comfy beds Lots of extra pillows, blankets, towels, cozy linens 🍼 Highchair, Pack n Play, toddler bed 🛀2 bathrooms including Whirlpool tub 🖥 2 TVs with Netflix, Prime, Disney+, Crave and Cable🍿 💻Fast internet, office nook 🚒Toys♟️games 🎲 Xbox 🎮 🔥Gas BBQ on the balcony 🔥Gas Fireplace 🚗Parking in shared lot NO. LCSTR20230000108

Superhost

Condo in The Blue Mountains

4.85 out of 5 average rating, 400 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Welcome to our beautiful studio at the foot of Blue Mountain ski hills. Fully renovated from top to bottom in 2021 and ready for visitors! 'Cascade Cabin' is a modern studio which sleeps 3 and features a King bed with a queen sofa bed in the living area. Unit features a fully equipped kitchen with seating for 3, full bathroom with shower & new soaker tub. The condo is located within minutes from Blue Mountain Village and within walking distance to the north ski lift.