
Pet-friendly holiday rentals in Midland
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Midland
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

RELAX @ our HOT TUB and SAUNA in the woods
PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

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.

Serenity, Simplicity and Stone
This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Cozy 4 Season Family Cottage
***NEW LISTING*** 4 season cottage, 5 min walk to beaches. Approx 1600sq. feet including 3 bedrooms and 1 large bathroom. Accommodates 6-8 Comfortably. Large Wrap around deck with outdoor furniture and greenery provided and BBQ Area to keep you relaxed and at home. Outdoor fire pit available. Situated on a private lot surrounded by nature. This getaway is equipped with everything you need - appliances and utensils, linens, Wifi, TV, board games, laundry with plenty more to do in the area.

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.

HOME ON BAY
A tranquil, beautiful & cozy 4-bedroom home for families and friends getting together. Walking distance to lake, groceries, LCBO, pharmacy, pub and restaurant. Close to numerous resorts and parks for summer and winter fun. Spacious kitchen and backyard deck are fully equipped with all your needs. Guests will enjoy all the entertainments both inside and outside all year round.. Daily rate is for 8 guests or less. No parties nor smoking allowed.

Pet-friendly, 1 BR condo in Horseshoe Valley
All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

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.

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Escape to Carriage Club Resort, nestled on rolling hills near Horseshoe Valley. Our 1-bedroom vacation rental sleeps 4 with a king-size bed and pull-out sofa. Enjoy the pool, firepit, volleyball, gym, and nearby skiing, golf, and Vetta SPA. Explore hiking trails, high ropes, and a 15-minute drive to Bass Lake's beach. Experience adventure and relaxation at Carriage Club!

Unique Tiny Home
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 280 square ft.
Popular amenities for Midland pet-friendly home rentals
Pet-friendly house rentals

Cozy Corner Townhome | Shuttle To The Village

Mountain Cedar Chalet! Across from The Village

Serene mountainside home with View/Shuttle Bus

Steps From the Beach and Hiking Trails!

Your Happy Place

Driftwood on 6th Heritage Downtown Collingwood

Beachy Blue Bay Cottage - licence #STRTT-2025-194

King Bed*Pool*Fireplace*BBQ*Smart TV
Pet-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course

Explore a Winter Wonderland at Blue Mountain

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

Base of Blue Mountain, Modern Studio

The Parker Slopeside: Hot Tub + Mountain Views

Oasis Spa w/ Private Sauna!

Utopia villa and spa

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

Kempenhaus- Lake Simcoe Cottage & Spa | HOT TUB

A modern retreat on Georgian Bay STRTT-2026-089

Georgian Bay Waterfront Cottage with Sandy Beach

Casa Tranquility

Glass Dome - Sleep Under The Stars- Free Sundays

Century Home in Bracebridge Muskoka w/ EV charger!

MegaMindful Living Air BnB Two

Forest Harbour Hideaway
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $225 NZD | $202 NZD | $201 NZD | $212 NZD | $211 NZD | $308 NZD | $315 NZD | $348 NZD | $358 NZD | $255 NZD | $222 NZD | $265 NZD |
| 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 |
Quick stats about holiday rentals that are pet-friendly in Midland

Total holiday rentals
Explore 70 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $83 NZD per night before taxes and fees

Verified guest reviews
Over 2,660 verified reviews to help you choose

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

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Midland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Midland rentals

4.7 Average rating
Midland stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Laurentides Holiday rentals
- Mont-Tremblant Holiday rentals
- Detroit Holiday rentals
- Waterfront rentals Midland
- Rentals with outdoor seating Midland
- Apartment rentals Midland
- Rentals with beach access Midland
- Beachfront rentals Midland
- Rentals with a washing machine and dryer Midland
- Family-friendly rentals Midland
- Rentals with pools Midland
- Rentals with lake access Midland
- Rentals with a fireplace Midland
- Cottage rentals Midland
- Cabin rentals Midland
- Rentals with a patio Midland
- Rentals with a kayak Midland
- House rentals Midland
- Rentals with a fire pit Midland
- Rentals with a hot tub Midland
- Fitness-friendly rentals Midland
- Rentals with an EV charger Midland
- Pet-friendly rentals Simcoe County
- Pet-friendly rentals Ontario
- Pet-friendly rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Three Mile Lake
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Torrance Barrens Dark Sky Conservation Area
- Kee To Bala
- Taboo Muskoka Resort & Golf
- Casino Rama Resort
- Bass Lake Provincial Park
- Wye Marsh Wildlife Centre
- Awenda Provincial Park
- Mono Cliffs Provincial Park
- Burl's Creek Event Grounds
- Couchiching Beach Park
- Menominee Lake
- Sunset Point Park
- Centennial Beach
- Orillia Opera House




