Family-friendly holiday rentals in Southampton

Secluded 1200' beachfront private 64 acre log home

Welcome to Dragonfly Cove Our log cottage features: *1200 feet of BEACH FRONT *Family-friendly, romantic, retreat *64 private forested acres, secluded cove on Lake Huron *Sleeps 10 (8 adults +2 children on futon) *Full view of lake & sunsets from spacious deck *Full kitchen with antique stove/oven combo *Stunning large glass sunroom *Central AC+heating *Gas+wood fireplaces *Bruce Tel internet *6 person hot tub *Firepit *2 kayaks *3000 acres of manicured trails at McGregor Point Provincial Park

Family Cottage close 2 everything room 4 everyone!

Large common spaces and lots of natural light make this a comforting space. Backing on to wooded trails, walking distance to everything, come and enjoy a slower more relaxed pace of life. At the beach, at the tennis club, on the river, in the woods, or in town. Or just hang with your favorite people on the deck, the screened poarch or around the big table. With heightened awareness of cleaning and safety we follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance.

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Drifter Lofts by West Shore 2 BR

Historic Beach Lofts. Boutique styled. Lakeview's and beautiful sunsets shared from Private deck. 2 huge bedrooms with King Size beds and closets. Full Kitchen + Baths. 2 washrooms. Beach, Lake and Stay downtown Kincardine at Drifter Lofts. Park your car and walk as you're in the middle of where you want to be. Drifter Lofts is located next to all of Kincardine's restaurants, harbour, lighthouse, beach, hiking trails, parks and more. Free parking on premise while you enjoy your stay.

Large Century Home at Driftwood Haus

Pet Friendly! Listen to the waves steps away! All newly renovated with brand new beds and furnishings. Enjoy the freedom. With the second best sunsets in the world according to National Geographic, Southampton is a community on the shores of Lake Huron in Bruce County, Ontario, Canada and close to Port Elgin. It is located at the mouth of the Saugeen River next to the Saugeen Ojibway Nation Territory. We have the most beautiful public beach in Ontario, a natural harbour and 3 lighthouses!

Holiday House on Huron

The location is truly special—just a short walk to boutique shops, local cafés, excellent restaurants, and a craft brewery. Whether you're here for the beach, biking the scenic Saugeen Rail Trail, or exploring the charm of small-town life, this is the perfect spot to experience it all. The open concept upper level is designed for gathering, entertaining, or simply unwinding in comfort. Main floor, you’ll find three cozy bedrooms (primary bedroom with ensuite), a full bathroom with bathtub.

Spa cottage: hot tub, sauna, cold plunge & firepit

Open plan bright cottage with Scandinavian inspiration including mid century modern furniture. Walk to beaches, bike trails and picturesque downtown (brewery, restaurants). Great for Fall hiking (Bruce Peninsula) and Winter snow shoeing and ice skating (McGregor provincial park) Go to an OHL game (Owen Sound), golf or yoga class. Outdoor spa: 7 person hot tub, 6 person sauna, cold plunge tub and fire pit. Pizza oven. Indoors: Fast wifi, table tennis and two fireplaces (natural gas)

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Awesome Lakefront Cottage with Private Shoreline

Enjoy exclusive use of our spacious lakehouse directly on Lake Huron. Gorgeous sunsets and view of Chantry Island. Huge deck with patio furniture with stairs to the lakeside garden with firestand. Bike, walk or blade along the paved lakeshore biking trail. Gas fireplace in livingroom for cooler evenings or your morning read. Fully equipped kitchen. Three bedrooms, lower level family room, three bathrooms, laundry facilities. We cherish our cottage. Respectful, five guests maximum.

The Nest at Victoria Street

Welcome to The Nest! This sweet, cozy 1-bedroom self-contained suite is part of a gorgeous century home in the heart of Southampton. Located one block from the main street, walking distance to downtown shopping, restaurants, parks, hiking, swimming as well as the best small town ice cream parlours. Directly across the street is a playground & splash pad for the kids. Enjoy a cocktail & BBQ on your private deck. Come relax & treat yourself to a vacation in our lovely beach town.

Pine Villa-Mediterranean Cottage with Hot Tub

Escape to our charming Mediterranean-inspired villa nestled in the serene countryside of Ontario. With minimalist aesthetics, the cottage offers a tranquil retreat for relaxation. Immerse yourself in the natural beauty that surrounds as you unwind on the patio or in the hot tub, or explore the countryside with our complimentary bikes. Inside, enjoy minimalist design, cozy details, and a nostalgic record player—where modern comfort meets rustic charm.

Dushi Beach House, Prime Southampton Location

Southampton Beach House is ideally located to take advantage of everything the area has to offer. Blocks to the beach, one block to High St (Southampton's Main St) and all of the great shops and restaurants. I purchased this 100+ year old house in Southampton in February 2021. From top to bottom the house was renovated and is basically brand new with all new furnishings.