Family-friendly vacation rentals in Southampton

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Southampton

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 343 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 favorite

Cottage in Lion's Head

4.94 out of 5 average rating, 155 reviews

Trails End Family Friendly Beach House

🍂 See the colours of fall! Welcome couples and families to our cozy cottage in the quiet village of Lion's Head. Open year round. One street up from the beautiful sandy beach and playground. A fully stocked kitchen, fresh linens, spotless kitchen and bathroom, BBQ, and large front deck. Campfire pit and dark skies for stargazing. Restaurants and shopping are all within a minute's walk. Great hiking trails nearby along the Bruce Trail. Complimentary wine. <40 mins from the Grotto & Sauble beach.

Guest favorite

Guest suite in Chatsworth

4.86 out of 5 average rating, 372 reviews

Settler's Loft in Log Home

This charming original log home is set amongst rock fences and mature maples on 80 acres of reforested farmland. This two-storey suite sleeps up to 5 guests, has 2 bedrooms, 4-piece bathroom, kitchenette, living area, deck, & private balcony. Trails for exploring, campfire ring, and large grassy area for outdoor games. Brand new AC system. Very close to OFSC snowmobile trails. (Note - barn access is for weddings only) NO pets >> 40 minute drive to Blue Mountain; 30 minutes to Lake Huron beaches

Guest favorite

Guest suite in Lion's Head

4.92 out of 5 average rating, 105 reviews

Beachfront Private Duplex near Grotto & Tobermory

Duplex unit in large private cottage. Hi speed Internet, heat pump air conditioning in summer. 35 minute drive to world class National Park/Grotto, Flower Pot Island and Tobermory. 15 minute drive to Greig's Caves, Lions Head, Bruce Trail/Niagara Biosphere Reserve. Eat in kitchen, picnic table. Two large queen bedrooms with bed linens. Tv room with single bed/small couch. Private deck, lawn and gardens, chairs. Beachfront water sports, deck, chairs, umbrella, fire pit. Kayaks, paddle board.

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 698 reviews

HeadWaters Retreat - Cozy Fireplace Suite

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with ensuite bathroom, Apple TV, steaming option and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Guest favorite

Cabin in Owen Sound

4.97 out of 5 average rating, 245 reviews

Cozy 'Off the Grid" Rustic Cabin

If you enjoy 'roughing it', stay in our beautiful log home from the late 1800's. It has been completely redone, maintaining all of the old character. It is nestled in the edge of the bush, that provides kilometres of hiking trails. The cabin is also situated on a pond so you can spend your days swimming, canoeing, fishing and exploring this nature lover's paradise. Spend your time here unplugging from your everyday life and reconnecting to the healing properties of a natural environment.

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 289 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:) Chef's creations and Private yoga and group classes available

Superhost

Cabin in Tobermory

4.91 out of 5 average rating, 235 reviews

Hudson's Rock Sauna Cabin Lake Huron Tobermory

Hudson's Rock located on the shores of Lake Huron just 10 min from downtown Tobermory. This cozy 3BR cabin is the perfect spot to make memories, whether cuddling up beside the cozy fire or playing board games with the family. Inside the warmth of the wood will instantly relax you while giving you all the amenities of home. Steps away from the waters edge, days can be spent swimming, kayaking, Sauna or soaking up the sun You'll have everything your family could want or need !

Guest favorite

Guest suite in Holland Centre

4.98 out of 5 average rating, 214 reviews

Dragonfly Hollow bnb

Nature lovers, Come experience the natural beauty of the Grey-Bruce region. Our home is in a very quite natural setting surrounded by trees. In summer explore the many lakes, beach or waterfalls . Hike the Bruce trail, or one of many others; good for ATVing, Scenic Motorcycle Routes. Fall is especially beautiful, the hills and valleys fill with vibrant colours. In winter, enjoy cross-country, downhill skiing, snowboarding, skidooing. Blue Mountain only a Scenic 40 mins away.

Superhost

Bungalow in Georgian Bluffs

4.8 out of 5 average rating, 139 reviews

Waterfront - Sunlight Cottage

Relax on the Georgian Bay waterfront deck after hiking the local trails or visiting the Bruce Peninsula! Take the stairs into the Bay for a swim. Chill under the pergola. Listen to loons, paddle the canoe, BBQ on the walk out deck, count stars by the fire pit, play games or have an air hockey tournament. Updated bathroom & kitchen. Air co. Apple TV's, 55" x2 & 32” tv screens. Unlimited high speed. Bunk beds are for children and folks under 160 lb.

Guest favorite

Rental unit in Kincardine

4.94 out of 5 average rating, 448 reviews

Lambton Place

LOCATION! LOCATION! LOCATION! Country charm meets urban chic in this stylish three-room suite in 100-year-old house. One block from the beach, one block from downtown shopping, restaurants and pubs. 1) Extra large bedroom, with closet, bureau, king bed; 2) Luxurious, four-piece, ensuite bathroom, with soaker tub, walk-in shower; 3) Sitting room with Wi-Fi, Smart-TV, cable; couch, chair, coffee-maker and small fridge. No kitchen.

Guest favorite

Cabin in Owen Sound

4.87 out of 5 average rating, 316 reviews

Heritage Reflections Guest House

Our place is perfect for someone looking for quiet, private place for a getaway. It is close to the Bruce Trail for hiking and Sauble Beach. We also are close to the Georgian Bluffs rail trail for cycling and hiking. Our guest house is great for couples, solo adventurers, and business travelers. We are a rural property with extensive gardens that you are welcome to explore and enjoy.