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

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.

Superhost

Home in Meaford

4.77 out of 5 average rating, 384 reviews

Serenity by Georgian Bay, 4 Season, escape!

This charming, cozy house offers serenity edge of town, by Georgian Bay! Suitable for couples, families and small groups. Across the street from the Bay. Comes with kayak, SUP and lawn games! Close to many Bruce Trails, Scenic Caves trails, or Georgian Trail, and golf. After a busy day exploring or playing, retreat to Meaford and either whip up something delicious in our fully equipped kitchen and dine in with a view of the bay, or walk down Sykes 5 min to one of Meaford's excellent restaurants.

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

Chalet in Priceville

4.91 out of 5 average rating, 462 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

Relive Retreat's Hilltop Chalet is a 700 sq ft open concept rustic cabin w/high ceilings, full-length windows, spring water, private + new hot tub, fireplace, BBQ, wrap around deck w/views, hiking trails + more. Perfect for couples, friends or families looking to relax & rejuvenate in nature. If peace is what you are looking for this is it! Occassionally dog friendly so please inquire first. This is a private 72 acre retreat. We live here with our 2 dogs, currently hosting 2 yurts and 2 cabins.

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

Home in Owen Sound

4.98 out of 5 average rating, 223 reviews

The Butchart Estate: your perfect family retreat!

Looking for a special place to spend some time? Make Butchart Estate your own, self-contained and private family retreat. Share precious time together and make some memories in this beautiful and well-equipped heritage home. Inside, enjoy the gourmet kitchen, relax in your own private indoor pool & hot tub, curl up by the fireplace, play board games galore. Free wifi. Outdoors, explore our beautiful nature walks, and local excursions. Enjoy a slower pace, and treasure some time together.

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

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.

Superhost

Cottage in Tiverton

4.79 out of 5 average rating, 179 reviews

Beautiful Lake Front Cottage

On the shore of Lake Huron. Enjoy the (literally) award winning sunsets, the gentle rolling of the waves while sitting on the deck or by the fire pit. Cottage feeling modern full kitchen and bathroom. 3 bedrooms: queen, double and double in the bunkie. See our youTube video titled "NEWSKOKA - Kincardine Cottage Rental" (sorry; Airbnb won't allow link)