
Family-friendly vacation rentals in Southampton
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Top-rated family-friendly rentals in Southampton
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Popular amenities for Southampton family-friendly rentals
Family-friendly home rentals with a hot tub

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
Thank you for the wonderful stay! Our group loved our stay! Would highly recommend.

Chalet At Blue - Private chalet with hot tub
Great communication with Shawn from start to finish, the home was what we expected and equipped with almost everything we needed. Lots of parking available, great spaces for groups to hang out, easy to host team meals. We were there for a ski trip and got pounded with snow, burying all sidewalks and making the walk to villages and chairlifts more difficult - but doable.

Stylish Log Chalet w/ Hot tub Minutes to Village
A MUST STAY!! Arriving late at night, outdoor lights greeted us & looked like the Idealic atmosphere for a fun weekend. Private & peaceful. We were delighted to find rustic charm, but with modern finishes and amenities. Tamara was so kind to check that we arrived ok & left me a sweet birthday message. We absolutely loved the upstairs bathroom with heated floors, stunning tub, & shower. The kitchen was a dream to cook in, everything you could imagine needing was provided, including ample cocktail glasses. The hot tub was quite big, 5 of us fit in there. The bedrooms were quaint & beds comfy. We just happen to be there during a massive ice storm. However, the cottage was the perfect - lots of wool blankets, the wood burning fire place heat up the cabin quickly & gas stove. Tamara was extremely helpful assisting us by locating safety supplies & great advice on how to ride out the storm. Her kindness & generosity turned our weekend to be one of the best memories, we will revisit for years

Deer Park, Cozy Cabin with Hot Tub, Amazing View
My family had an amazing stay at Jennifer's cabin! We came for a ski weekend with our 2 young kids and our dog. It was just a short drive to the ski hill, but the cabin was situated a ways back on the property and we felt like we were in our own winter wonderland. The cabin had everything we needed, including board games! and the wood stove kept us nice and warm. We enjoyed hiking around with our dog and also spending time in the hot tub. Jennifer was very communicative & responsive and we felt extremely taken care of and welcome. We hope to come back again one day!

Century Home in downtown Owen Sound - Hot Tub
Excellent place to stay. Very clean. Very accommodating.

Rustic Spanish Chalet inthe Heart of Nature/hottub
We booked this home for a family and friends cottage weekend and the place was exactly as described. It is a beautiful home very close to the slopes with lots of things to do (billiards, board games, hot tub, TV, BBQ). The host was very kind and responsive and was very flexible with out checkout time, which was very nice. Our group of 11 people all had a great weekend and we would definitely book this place again :)

ReLive Hilltop Chalet w/brand-new hottub, sunrises
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.

Waterpark Acres
Extremely beautiful, peaceful and spacious! House is comfortable, spotless and has enough spaces to relax and lounge around!! The views are amazing and the big windows allow lots of sunshine in. Kitchen is fully equipped to make meals and it was spotless! More than enough clean bedding and towels were available. Cleon and Christine have thought of every little amenity and provided for it. Everything was perfect and we thoroughly enjoyed our stay. The highlight is and always will be the variety of animals Cleon has and takes care of. His love for them is evident and he has thoughtfully provided them with warming sheds when it gets too cold. All the animals looked very well taken care of and content.. we enjoyed feeding the lemurs, marmosets, kangaroos, sheep, various birds, Guinea pigs.. and quite a few I am definitely missing 😊 Cleon set up a fire for us and it was very enjoyable and peaceful.. the ponds are so so beautiful and the sound of the waterfall is relaxing. We will be back!
Family- and pet-friendly home rentals

Blyth Brook Cottage
I've stayed about five times at the Cottage. We go back because we love the space it's so open, and outside there's so much green space and so much to do depending on the weather! We always enjoy a night at Cowbell which is so close! On cold nights you can snuggle by the fireplace and keep warm and cozy. The hosts were great at keeping the snow out of the laneway so we could get in and out. Thanks again Melanie we really had a great time!

The SEED lodge: A Rural Retreat & Gathering Place
Awesome place for our friend group to get together (families with kids ages 3-11) Tons of cooking spices, bowls, plates, mugs. Sauna is a nice touch and so is the fire pit. Large property for the kids to run around. I wasn't sure about the single beds but they were very comfortable. Nice bathroom/shower set up. Perfect for a large group. Would go back!

Heron's Perch
This was our second year at Carrie and Dan's cottage and once again my family and I had a fantastic time. The house is perfectly situated on the river with a nice beach and it has all of the amenities needed. Dan communicated regularly and checked in with us to ensure we had everything we needed. This is a beautiful property which anyone would have fun at.

Due North ★ Lake House
This place is a real treasure! The sandy beach is gorgeous out front. Lots of outdoor seating space. I liked that it was surrounded by trees at the back but open to the water and sand in the front. It's cozy and the kitchen has everything you need. I loved the fireplace and the beds and couch were comfortable. I was there in April and it was very quiet.... I didn't see anyone on the beach or around it. It is a short drive to great hiking and a grocery store that has all you need. I would definitely return!

Crystal Water Retreat includes 6 Kayaks
This place was amazing! Beautiful views and lovely living room. We loved the kayaks and the fire pits and the hosts were very accommodating and responded quickly. We would definitely come again!

All-Season Cottage on the Lake
Great place in a beautiful location! Perfect for our two families to get together and enjoy the outdoors in winter. The kitchen is well-supplied and it’s great to have towels and sheets provided. Carrie is friendly, flexible and well organized. Thanks so much!

Blue Barn Bed n Bale / Blue Mountain
We really enjoyed our stay in Kim’s spacious barn, with friendly horses and great views right outside the front door. We have loved exploring the area over the years and this is one of our more unique experiences.

Serenity by Georgian Bay, 4 Season, escape!
Great location for hiking the Bruce Trail ! Wonderful view of the water.
Family-friendly home rentals with a pool

Blue Mountain / Collingwood Hill Side Condo
The host was very clear on instructions and the place was spotless. Great location and space for two people Unfortunately, with the heavy rain, there seems to be a hole on the sliding door of the balcony that let water in enough to pool on the floors and got our stuff wet. The host said it will be fixed

The Snowbridge Lookout on Monterra Golf Course
Beautiful condo, very clean, the most comfortable beds. Only downside is there is no bathtub We will return forsure

Luxury Vacation Home at Blue Mountain Village
This was a beautiful place with great views, only a 5 minute walk away from the village. It was clean with an organized bathroom and kitchen amenities. We weren’t missing anything. There was a nice fireplace with a lot of board games. Super cozy, and a great place to take photos. You also had access to a shared hot tub. Sometimes other people got rowdy at the hot tub, but that is to be expected. Overall this is a great place for families or get togethers for skiers and people that like great restaurants and social events. Thanks, Adam!

Cozy Blue Mountain Retreat @!@Great Rates@!@
Not my first time at this apartment, I guess that says it all.....

Rustic Cottage At Campground
Jodi was so helpful and accommodating. The cottage was perfect. Everything we needed and so much more on the grounds. Lots of places within a short drive for things to do.

Heart of Kimberley - with views and a hot tub
Great gals weekend. We really enjoyed the General Store and exploring the area. The house linens were great, beds comfy and the seating areas too :) Weather wasn't conducive to using the outdoor spaces and as older folks we didn't think we'd manage the step stool to get into the hot tub. If there's a next time, we'll try the bustling "Justin's Oven" !!

2 Bedroom, 2 Level Condo on Blue Mountain!
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.

Rustic Mountainside Chalet
Cozy, clean appartment with all the ammenities we needed.
Quick stats about vacation rentals that are family-friendly in Southampton
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
3.3K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
100 properties include access to wifi
Destinations to explore
- Grand River Vacation rentals
- Brampton Vacation rentals
- Muskoka Lakes Vacation rentals
- Georgian Bay Vacation rentals
- Waterloo Vacation rentals
- Kitchener Vacation rentals
- Tobermory Vacation rentals
- The Blue Mountains Vacation rentals
- Barrie Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Beachfront rentals Southampton
- Rentals with a washer and dryer Southampton
- Rentals with a patio Southampton
- Rentals with outdoor seating Southampton
- Rentals with a fire pit Southampton
- Rentals with lake access Southampton
- Kid-friendly rentals Southampton
- Pet-friendly rentals Southampton
- Cabin rentals Southampton
- Condo rentals Southampton
- Rentals with a fireplace Southampton
- Rentals with a hot tub Southampton
- House rentals Southampton
- Cottage rentals Southampton
- Rentals with beach access Southampton
- Family-friendly rentals Bruce County
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom