
Pet-friendly vacation rentals in Midland
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Midland

Total vacation rentals
Explore 60 vacation rentals in Midland

Nightly prices starting at
Midland vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 2,700 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Midland vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Midland rentals

4.7 Average rating
Midland stays receive an average rating of 4.7 out of 5 from guests
Top-rated pet-friendly home rentals in Midland
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Summer Getaway - 3 min walk to Beach, Clean & Cozy
Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

White Rolling Sands of Penetang by Theatre
Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

The Cottage on Coldwater; where bay & trail meet.
Georgian Bay on one side and the Tay Trail on the other, this lakeside cottage offers gifts for all seasons. With spectacular views of the bay ready 4 ice fishing, sledding, skiing and snow shoeing over winter; hiking, biking, boating and swimming over summer with infinite possibilities in between, we're sure Waubaushene will suit your needs. Close to quaint Coldwater stores, kilometers of Parks, a short drive to 2 ski hills and just off Hwy 400, this hidden gem can accommodate adventure.

Ultimate Georgian Bay Vacation Getaway
Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Muskoka Stunning Cottage On Little Lake
Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Charlie the Cottage | Hot Tub | Trail | Hike/Run
Modern cottage with sunset views of Georgian Bay right on the paved Tay Shore Trail for running/biking/snowshoeing. Newly renovated from top to bottom! Enjoy the 500 sqft deck with year round Hot Tub, BBQ and patio table. Fire pit in the backyard. The house is on a large lot surrounded by evergreens for privacy. Across the trail you can access the water, 5 min walk to a sandy beach. 1.5hrs from Toronto, 30mins north of Barrie, 12mins to Mt St Louis Moonstone for skiing.

Woodland Muskoka Tiny House
**BOOK 7 NIGHTS, PAY FOR 5 (28% OFF)** Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka.

Chirping-Paradise Glamping Dome
Recharge in a peaceful four-season glamping dome set on 10 acres of forest trails, streams, a pond, and seasonal apple trees. Enjoy fast Wi-Fi, cozy interiors, and a wood-pellet stove for winter stays. A welcoming nature escape for couples and families, close enough for a quick getaway from the city. Outdoor scenery and fruit vary by season; please ask the host before picking apples or other fruit

A-Frame Hidden in the Forest Muskoka, Georgian Bay
Welcome to our A-frame /Triangle House, Wifi, Sauna, Kitchen, A/C, Free Parking, King Bed, FIFA friendly, Smart Tv, Peaceful, Social Media Favourite, Top Choice for city escape, and an ideal weekend getaway. Come heal, enjoy the light luxury in nature, and enjoy the slow living at this premium vacation experience. Rare architecture, designer cabin. Come and gather energy in this forest sanctuary.

Private 40 Acre Cottage with Hot Tub
Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

Cozy Beach Cottage with Pool | Georgian Bay
Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Unique TinyHome
This is a unique space with great attention placed on details. I design and build unique livable spaces catered to the individual needs of my clients. I invite you to come experience high quality living in a modern tiny home and experience sustainable, affordable living in just 286 square ft.
Popular amenities for Midland pet-friendly home rentals
Pet-friendly house rentals

Mountain Cedar Chalet! Across from The Village

Birdsong, the perfect Blue Mountains getaway

3BR Spacious Home - KING BED

Paradise Point Steps from Georgian Bay Great WIFI

Luxury Guest House with Private Hot Tub and Trails

Steps From the Beach and Hiking Trails!

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Bayside Serenity | Parking | Midland Cottage
Pet-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course

Cozy 1-Bedroom Romantic Retreat with full Kitchen

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

The Parker Slopeside: Pool, Hot Tub, Tennis, Views

Oasis Spa w/ Hot Tub-Private Sauna-Oasis Patio

Utopia villa and spa

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Pool, Wifi, Free parking, Golf, Laundry, BBQ
Private, pet-friendly home rentals

Kempenhaus- Lake Simcoe Cottage & Spa | HOT TUB

Georgian Bay retreat - apartment in Midland

Serenity, Simplicity and Stone

Cottage on the Rocks - with Hot Tub and Sauna!

Hidden Gem

Tiny A-Frame near the Bruce Trail

Glass Dome - Sleep Under The Stars- Free Sundays

OakRidge Retreat-HOT TUB 100s of acres WIFI
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $218 CAD | $216 CAD | $177 CAD | $218 CAD | $229 CAD | $259 CAD | $265 CAD | $293 CAD | $301 CAD | $215 CAD | $187 CAD | $223 CAD |
| Avg. temp | -7 °C | -6 °C | -1 °C | 6 °C | 12 °C | 17 °C | 20 °C | 19 °C | 15 °C | 9 °C | 3 °C | -3 °C |
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- Blue Mountain Village
- Wasaga Beach Area
- Torrance Barrens Dark Sky Conservation Area
- Beaver Valley Ski Club
- Killbear Provincial Park
- Awenda Provincial Park
- Scandinave Spa Blue Mountain
- Menominee Lake
- Casino Rama Resort
- Georgian Bay Islands National Park
- Sibbald Point Provincial Park
- Three Mile Lake
- Bass Lake Provincial Park
- Wye Marsh Wildlife Centre
- Centennial Beach
- Mono Cliffs Provincial Park
- Sunset Point Park
- Couchiching Beach Park
- Innisfil Beach Park
- Kee To Bala
- Burl's Creek Event Grounds
- South Muskoka Curling and Golf Club
- Craigleith Provincial Park
- Orillia Opera House





