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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.

Gorgeous Winfield Chalet Cottage - Midland
9.9 91 reviews

Gorgeous Winfield Chalet Cottage

cottage, Midland
This charming cottage is situated in Victoria Harbour, just a 10-minute walk from the local sandy beach, restaurants, and a supermarket, and within a 15-minute drive of Midland Cultural Centre and Mount St. Louis. The property has received excellent ratings for user experience, location, and cleanliness.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to nine guests. Enjoy a fully equipped kitchen, a spacious recreation room with games, a heated swimming pool, and a large garden with a fire pit, trampoline, and swing set for entertainment.

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.

Modern 4br Cottage, Hot Tub & Sauna On Tay Trail - Midland
9.4 245 reviews

Modern 4br Cottage, Hot Tub & Sauna On Tay Trail

house, Tay
This four-bedroom house is located in Waubaushene, just 19 kilometres from Orillia Community Centre Arena and 12 kilometres from Midland Cultural Centre. The area offers a peaceful setting with easy access to Georgian Bay, trails, and nearby attractions. This property has received excellent user ratings for location, cleanliness, and overall experience.
This spacious 111 square metre property comfortably accommodates up to eight guests. The house is equipped with modern amenities including a fully equipped kitchen, a fireplace, a hot tub, a sauna, a tennis court, and a private garden, making it ideal for families and groups seeking a relaxing and enjoyable stay.
3br Townhome | Georgian Bay | Free Parking - Midland
10 51 reviews

3br Townhome | Georgian Bay | Free Parking

house, Midland
This modern three-bedroom house is situated in a peaceful subdivision near Little Lake in Midland, within easy walking distance of the Martyr's Shrine and a short drive from Georgian Bay's attractions. The property has received excellent ratings for location, cleanliness, and user experience.
The spacious home offers ample room for up to eight guests and is equipped with a fully fitted kitchen, a comfortable living area with a large TV, and a combination washer and dryer. Guests can enjoy high-speed internet, parking for two cars, and a peaceful location close to a range of outdoor activities including boating, hiking, beaches, bicycling, skiing, and skating.
Modern Waterfront Home On Georgian Bay W/ Hot Tub! - Midland
9.7 109 reviews

Modern Waterfront Home On Georgian Bay W/ Hot Tub!

house, Midland
This modern waterfront holiday home is situated in a quiet neighbourhood in Victoria Harbour on Georgian Bay, just a short drive from the charming town of Midland and attractions like the Tay Shore Trail and the Wye Marsh Wildlife Centre. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy breathtaking views of Georgian Bay from the walkout deck, relax in the hot tub, and make use of the private dock, kayak, and canoe for exploring the bay.
Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 2 reviews

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.

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

Guest Unit - Midland
9.8 30 reviews

Guest Unit

house, Midland
This brand-new, three-bedroom self-catering apartment in Midland, Ontario, is located minutes from Georgian Bay, offering easy access to water activities and scenic trails.
The 3-bathroom property sleeps six guests and boasts modern amenities including air conditioning, parking, and Wi-Fi, alongside a comfortable and stylish layout perfect for families.
Blue Water Dunes Cottage - Midland
9.8 4 reviews

Blue Water Dunes Cottage

chalet, Tiny
This beachfront chalet is located in Tiny, Ontario, just 22 kilometres from the Tay River Basin and 47 kilometres from Barrie South GO Station, offering a peaceful escape in a scenic setting. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The chalet has four bedrooms, three bathrooms, and covers 186 square metres, comfortably accommodating up to 15 guests. Enjoy a range of amenities including a private beach, hot tub, barbecue facilities, a garden, and a mini-golf course, perfect for relaxation and entertainment.
Waterfront 3 Bedroom Home - Midland
No reviews

Waterfront 3 Bedroom Home

house, Midland
This waterfront dwelling is located in Port McNicoll, 8.5 kilometres from Tay River Basin and 9.8 kilometres from Midland Cultural Centre.
Offering 280 square metres of living space, this detached house accommodates up to 11 guests with 3 bedrooms and 2 bathrooms, boasting a well-equipped kitchen, air conditioning, a terrace with lake views, an outdoor fireplace, and on-site water sports facilities.
Farm Stay Getaway - Midland
10 3 reviews

Farm Stay Getaway

cabin, Tay
This cosy 8x12 bunkie, offering accommodation for two guests, is situated on a secluded 100-acre woodland and riverfront property in Tay, providing direct access to hiking trails and forests. Guests can enjoy a riverfront location with swimming and fishing opportunities, a fire pit, basic kitchen amenities, electricity, potable water, and an on-site outhouse, all within a tranquil rural setting.

Best Midland villas and holiday homes with a garden

Forever Memories - Midland
9.0 2 reviews

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.
Central Charming Farm + Fireplace + Walking Trails - Midland
10 9 reviews

Central Charming Farm + Fireplace + Walking Trails

gîte, Tay
This private, furnished 56 square meter gîte is located on an 8-acre hobby farm in Tay, a 16-24 minute drive from Midland, Penetanguishene, and Elmvale, offering a peaceful rural escape.
This accommodation sleeps up to three guests and features a sleeping loft accessible by ladder, a kitchen with a fridge, freezer, and microwave, and access to walking trails, a shared firepit, and nearby snowmobile and ski trails at Mount St. Louis Moonstone.
Comfy Thoughtful Private Cottage - Midland
9.5 2 reviews

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.
Tiny House In Penetanguishene - Midland
9.9 250 reviews

Tiny House In Penetanguishene

house, Midland
This charming one-bedroom apartment is situated in Penetanguishene, just 5km from a public beach and 9km from Discovery Harbour and the King Wharfs Theater. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment sleeps up to four guests and features a fully equipped kitchen, a private fenced backyard with a deck, and high-speed internet access. Guests can enjoy barbecuing, relaxing in the garden, or exploring the nearby attractions.

Uncover Luxury Holiday Homes in Midland

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

House On The Hill, Hottub, Relaxation, Bike Trails - Midland
9.7 263 reviews

House On The Hill, Hottub, Relaxation, Bike Trails

house, Midland
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