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Midland villas
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52 Villa rentals in Midland

Holiday Homes with a Pool in Midland

Enjoy an exclusive swim in total privacy right in your own backyard at houses featuring a swimming pool in Midland.

Spacious -Custom Build Lakehouse-strtt-2026-127 - Midland
9.4 10 reviews

Spacious -Custom Build Lakehouse-strtt-2026-127

cottage, Tiny
This luxurious waterfront holiday home in Tiny, Ontario, is a 20-second stroll from a child-friendly beach with shallow waters and offers easy access to Lake Huron, with Sainte-Marie among the Hurons and Martyrs' Shrine within driving distance.
The 242-square-metre (2600 sq ft) property boasts four bedrooms, three bathrooms, sleeps ten guests, and includes a private hot tub, swimming pool, spa, and extensive amenities such as a gas fireplace, bicycles, and high-speed internet with access to popular streaming services.

Delightful Family-Friendly Houses in Midland

Give the family a spacious home base with private yards and room for everyone at family houses in Midland.

Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 1 review

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
This waterfront holiday home in Tay offers direct access to shallow waters via a private dock and is located approximately 1.6 to 2.4 kilometres from the Huronia Museum and Ste-Marie among the Hurons.
This spacious 230 square metre lodge comfortably accommodates up to 10 guests across four bedrooms, featuring a modern kitchen with a wine fridge, a gas fireplace, a wood-burning barrel sauna, kayaks, and parking for seven vehicles.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.6 8 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This family-friendly Tiny lakeside retreat, a 10-minute walk from Lake Huron and Georgian Bay, is situated within 15km of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 279 square metre property boasts four bedrooms, three bathrooms, sleeping eight guests, and features a fully equipped kitchen, jacuzzi, sauna, tennis court, and free Wi-Fi.
Victoria Harbour Cottages - Midland
9.3 29 reviews

Victoria Harbour Cottages

house, Midland
Victoria Harbour Cottages are located on the beachfront in Victoria Harbour, just 5.5 miles from Tay River Basin and 29 miles from Lake Simcoe Regional Airport. The cottages have received excellent ratings for location, cleanliness, and overall experience.
These one-bedroom cottages offer a comfortable and convenient stay for travellers. Enjoy the on-site amenities, including a fully equipped kitchen, private balconies, and access to free bikes for exploring the beautiful surroundings.
Cheerful 4-bedroom Cottage In Nature Setting - Midland
10 2 reviews

Cheerful 4-bedroom Cottage In Nature Setting

cottage, Waubaushene
This five-bedroom lakeside property in Waubaushene, Ontario, offers stunning waterfront views of Lake Huron and Georgian Bay, being less than 1.6km from Juanita Island and Bayview Park.
Sleeping eight guests, the self-catering holiday home boasts a fully equipped kitchen, a patio, garden, and parking, plus access to swimming, boating, and fishing opportunities.

Frequently asked questions about villa rentals in Midland

  • What are the must-see attractions in Midland?

    Midland's got some real gems. You can't miss the Midland Bay Marina, it's a bustling hub for boaters. And if you like history, the Huronia Museum is a must-visit, with loads of exhibits on the region's past. Plus, the iconic Midland Lighthouse is a great spot for photos.
  • What are the best villa rentals in Midland?

    Among the villa rentals in Midland, Sunset Beach Cottage, The Little Lake House and House On The Hill - Hottub - Ski - Ice Fish - Trails are the most popular ones.

  • What indoor activities for families are available in Midland on rainy days?

    For a rainy day, head to the Midland Public Library. They've got a great kids' section, and there are often events for families. If you're feeling active, the Midland YMCA has a big indoor pool and play area. You could also check out the Midland Cinema, they show a variety of films.
  • What are the best villa rentals with a pool in Midland?

  • What are the best activities in Midland?

    Midland has something for everyone. In summer, you can spend the day at Little Lake Park, swimming, picnicking, or just enjoying the scenery. The waterfront trail is great for walking or cycling. And if you're into fishing, the Bay is a great spot to cast a line.
  • What are the best villa rentals with a jacuzzi in Midland?

  • What are the advantages of renting a house or a villa in Midland

    Renting a house or villa in Midland gives you more space and privacy compared to a hotel. You can cook your own meals, which is often cheaper. Plus, many rentals come with amenities like a backyard or patio, perfect for relaxing after a day of exploring.
  • What are the best villa rentals for families and kids in Midland?

  • What food festivals or culinary events take place in and around Midland?

    The biggest food event in the area is the Midland Farmers' Market, held every Saturday from May to October. You'll find local produce, baked goods, and artisan crafts. The annual Midland Waterfront Festival also features a variety of food vendors and live entertainment.
  • What are the best pet friendly villa rentals in Midland?

  • What exclusive experiences are available when visiting Midland?

    For something unique, consider a sunset cruise on Georgian Bay. There are several companies offering tours, and you'll get stunning views of the water and the surrounding islands. You could also book a private fishing charter and try your luck at catching some local fish.
  • What are the best villa rentals with parking in Midland?

    Sunset Beach Cottage, The Little Lake House and Serenity - Simplicity And Stone are the best villa rentals with parking in Midland.

  • Which part of Midland would be ideal for a villa rental?

    The area around Little Lake Park is popular for villa rentals, as it's close to the water and offers easy access to downtown Midland. You'll find a mix of modern and traditional homes, many with beautiful views of the lake.

Popular destinations

Best Midland villas and holiday homes with parking

Beachside Bungalow  Steps From Balm Beach! - Midland
No reviews

Beachside Bungalow Steps From Balm Beach!

cottage, Tiny
This holiday home is located in Tiny Township, just a few steps from Balm Beach, offering direct access to local restaurants, an arcade, shops and a public children's playground, with Midland and Penetanguishene accessible within a 10-kilometre drive.
This 27 square metre lodge accommodates up to four guests with two bedrooms and one bathroom, featuring air conditioning, high-speed WiFi, a full kitchen, a Smart TV, a sunroom with partial lake and beach views, a fire pit, outdoor seating, a BBQ, and lawn games, with pack n' play and high chair available on request.
Cottage With A Million Dollar View - Midland
No reviews

Cottage With A Million Dollar View

cottage, Tay
This Georgian Bay holiday home is located near Midland, offering direct waterfront access and a flat lawn perfect for games.
This three-bedroom property comfortably accommodates six guests and features air conditioning, a kitchen, and internet access, with opportunities for swimming and fishing right on your doorstep.
Georgian Bay Cottage 2 Bedrooms - Midland
No reviews

Georgian Bay Cottage 2 Bedrooms

gîte, Midland
This rural holiday cottage is located a stone's throw from a paved cycle path and Georgian Bay, offering a distinctive outdoor-focused experience near Midland.
This self-catering accommodation for up to 10 guests provides 6 bedrooms, 3 bathrooms, a functional kitchen, and indoor plumbing, with flexible rental options and a unique 'glamping' style without the need for a tent.
Red Rustic Cabin By The Beach - Midland
No reviews

Red Rustic Cabin By The Beach

cabin, Midland
This 3-bedroom, 3-season cottage in Midland is located on the shores of Georgian Bay, offering exclusive access to a private, members-only beach directly across the street.
This pet-friendly lodge accommodates up to eight guests and features a kitchen with a fridge and microwave, air conditioning, a garden, parking, and a unique outdoor shower alongside an indoor powder room for an authentic cottage lifestyle experience.

Best Midland villas and holiday homes with a garden

Forever Memories - Midland
10 1 review

Forever Memories

cabin, Midland
This new log lodge in Midland offers a peaceful escape, conveniently located a short drive from Penetanguishene and Midland's attractions.
This four-bedroom, four-bathroom property accommodates up to ten guests and features air conditioning, internet, a kitchen, and a jacuzzi, making it ideal for family holidays.
Comfy Thoughtful Private Cottage - Midland
10 1 review

Comfy Thoughtful Private Cottage

house, Springwater
This detached property is located in a Springwater district, offering convenient access to local attractions and amenities.
This 10 square meter bungalow accommodates up to 15 guests, featuring a private terrace, free parking, complimentary WiFi, a fully equipped kitchen, and air conditioning.
Cottage On Water At Oak Bay Gulf Club - Midland
9.8 6 reviews

Cottage On Water At Oak Bay Gulf Club

cottage, Port Severn
This Georgian Bay holiday home is situated a short distance from both Lake Huron and Georgian Bay, and 2.3 kilometres from the Oak Bay Golf Club.
Sleeping up to eight guests, this two-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, laundry facilities, a patio, and barbecue grills; enjoy on-site amenities and the nearby attractions of Georgian Bay.
Luxury Log Cabin With Work Spaces, Generator And Car Charger - Midland
9.6 22 reviews

Luxury Log Cabin With Work Spaces, Generator And Car Charger

apartment, Tiny
This family-friendly Tiny holiday home is situated near Georgian Bay and Lake Huron, just 0.5 km from Awenda Provincial Park.
The three-bedroom property sleeps eight, boasting a fully equipped kitchen, free Wi-Fi, a terrace, garden, parking, and on-site amenities including a water park and hot tub.

Uncover Luxury Holiday Homes in Midland

Find luxury houses in Midland for a spacious and upmarket small-city retreat.

Cabin Peace Georgian Bay On Tay Trail, Pre-summer May/june Save 20% - Midland
9.6 5 reviews

Cabin Peace Georgian Bay On Tay Trail, Pre-summer May/june Save 20%

cabin, Tay
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