Vacation rentals with a pool in Bruce County

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)

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.

Custom Mansion on the Water | Pool | Hot Tub

*Minimum days* Looking for long term guest* An estate like no other! Our 6000 sqft home is located in the heart of Owen sound on the Sydenham On one side of the house is a modern open concert Kitchen/Living/Dining with a walk out to the huge backyard. On the other side, we preserved the Victorian style roots with original art, furniture and style. Amenities include a large in ground pool, hot tub, sauna, pool table, games room and much more. Enjoy waterfront access right from the backyard!

The Lighthouse Pool house

Make some memories at this unique, family-friendly bed & coffee rental. The Lighthouse Pool house is a traveller's delight! This guesthouse has one bedroom, kitchen area & an indoor swimming pool, within your hosts residence. We offer endless cups of coffee during your stay! Enjoy your brew on the poolside patio, listening to the birds & waves from the lake across the road. Your stay includes a fridge, cook top, microwave, toaster, keurig, bbq & firepit. Keypad locks used for pool safety!

Cozy Tiny Home at Kenorus

Welcome to your perfect getaway at Kenorus - Revive Resorts. Located just minutes from beautiful beaches of Lake Huron. This 2 bedroom including loft is thoughtfully designed to maximize comfort and style. Perfect for families and couples, the home includes two queen beds, fully equipped kitchen with all the essentials. A/C and a full bathroom with modern finishes. It also includes small deck with picnic table and fire pit. Amenities include family pool, adult pool and splash pad.

Southampton Retreat: Pool & Spa

Escape to this luxurious 5-bedroom, 4-bathroom retreat in Southampton, Ontario! Perfect for families, this home features a private pool, hot tub, and steam bath for ultimate relaxation. Just minutes from the beach, enjoy spacious living areas, a fully equipped kitchen, and outdoor lounging. Whether you’re unwinding by the pool or exploring the town, this getaway offers the perfect blend of comfort and serenity. Book your stay today! This unique place has a style all its own.

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.

Welcome to the Tiny Honey House!

Summer is on its way and it is time to think about a relaxing get away at the Tiny Honey House! Our tiny home is centrally located on the Bruce Peninsula close to popular Sauble Beach, Tobermory and the Bruce Trail. After a day of adventures have a dip in the above ground pool or relax in the hot tub. There is a good chance of spotting the northern lights while sitting with your favorite beverage around a roaring camp fire watching the night sky.

Luna Log House | Sauna + 5 Bdrm

Escape to the Luna Log House, a beautifully renovated 5-bedroom log home nestled on 10+ private acres of protected woodlands. The Luna Log House is sought after as a 4-season location for families and groups of friends to enjoy the outdoors and relax indoors. This serene retreat offers the perfect blend of rustic charm and modern comfort, complete with a cedar barrel sauna, fire pit, and a fully equipped kitchen perfect for the gourmet chef.

Waterfront Unit #2 on Spry Lake

You’ll treasure your time at this memorable place. This new park model unit is located on the WATER at this family campground. The unit features two bedrooms (a Queen, a double and a pull out couch). Park models are very similar to tiny houses as they have all that you will need to come and relax. You also get to have the camping experience while being at a campground (fire pit, bbq)

#6 Downtown Studio weekly/monthly stay downtown

This private space is set up for those who wish to be close to everything downtown but tucked away from the busy street. Walk to everything downtown or to the shops to the east. This well appointed studio apartment has everything you need to cook up a meal, enjoy a super large shower, land just hibernate after a busy day. Weekly and monthly stays encouraged for best savings.

Rustic Vibes w/ Pool & Hot Tub - Tobermory

Escape to an authentic cottage retreat where comfort meets adventure. Lounge on the expansive deck under a canopy of stars or take a refreshing dip in the private pool. With room to relax and explore, every moment is yours to shape. Ideally situated just minutes from Tobermory’s top attractions—this is more than a stay, it’s a getaway with endless possibilities.