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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.

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Guest suite in Moonstone

4.83 out of 5 average rating, 164 reviews

SKI, Trails 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.

13–18 May

$252 NZD per night

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 118 reviews

Cozy 4 Season Family Cottage

***NEW LISTING*** 4 season cottage, 5 min walk to beaches. Approx 1300sq. 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.

21–28 Sep

$312 NZD per night

Guest favourite

Home in Penetanguishene

4.97 out of 5 average rating, 143 reviews

White Rolling Sands of Penetang by Theatre

Enjoy a firepit in the private backyard of a large deep lot backing onto woods with trails. Local walking and cycling routes, or stay home and enjoy the veggie and flower gardens from 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 are nearby.

30 May – 6 Jun

$211 NZD per night

Cottage in Waubaushene

4.81 out of 5 average rating, 126 reviews

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.

4–11 Jun

$265 NZD per night

Guest favourite

Apartment in Orillia

4.95 out of 5 average rating, 146 reviews

Your Downtown *Hot Tub* Getaway!

This Incredible unit is the perfect blend of style, luxury & convenience. Filled With all the amenities you look for with the touch of luxury that you would expect in a hotel. Spend your evenings relaxing with a glass of wine in the private hot tub area, immersing yourself in the cinematic feel of the 65" TV, or walking through the bustling downtown streets of Orillia on the way to catch the sunset at the waterfront. However you choose to spend your stay, there is much to enjoy! 🤩

31 Jul – 7 Aug

$238 NZD per night

Guest favourite

Cottage in Port McNicoll

4.98 out of 5 average rating, 125 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

5–12 Oct

$235 NZD per night

Guest favourite

Dome in East Gwillimbury

4.92 out of 5 average rating, 129 reviews

Deerleap Glamping Dome

Looking for a peaceful escape from the city? Our glamping dome offers just that, situated on 10 acres of picturesque land with trail, streams, and a stunning pond view. Perfect for a romantic retreat or a weekend getaway with the family, our dome is equipped with everything you need, from upscale sanitary to fast Wifi. Relax and enjoy the starry sky from the comfort of your bed, gather around the bonfire for s'mores , or explore nearby Lake Simcoe.

15–20 Nov

$361 NZD per night

Guest favourite

Bungalow in Victoria Harbour

4.91 out of 5 average rating, 118 reviews

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.

20–27 Jun

$331 NZD per night

Cottage in Port Severn

4.86 out of 5 average rating, 130 reviews

Cottage "Down By The Bay"

1 bdrm cottage in beautiful Port Severn, ON with firepit, WIFI, Heat and AC. Great location year round. Located on the main road into Honey Harbour, ON and close to amenities such as Tim Hortens, LCBO, gas stations and restaurants. Near water and beaches (NOT A WATERFRONT- Port Severn Park and Beach is 7 min drive) Right beside entrance to OFSC trails for snowmobiling Mount ST. Louis is a 20 min drive Fishing/ice fishing options nearby

10–17 Jan

$168 NZD per night

Guest favourite

Cottage in Tiny

4.95 out of 5 average rating, 196 reviews

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.

22–29 Jul

$696 NZD per night

Guest favourite

Tiny home in Waubaushene

4.97 out of 5 average rating, 289 reviews

Unique Tiny Home

This truly 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 275 square ft.

13–20 Jul

$212 NZD per night

Guest favourite

Home in Port McNicoll

4.94 out of 5 average rating, 184 reviews

Spectacular Waterfront 3 Bedroom Home!

Beautiful 3 bedroom newly built waterfront house on Georgian Bay! Located in a quiet area with a beach! In the summer the lake is perfect for swimming! Just bring water shoes as there can be rocks and zebra muscles. This 3 bedroom waterfront home is the perfect place for a summer or winter getaway!

7–14 Sep

$642 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Midland pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Guest favourite

Home in Penetanguishene

4.98 out of 5 average rating, 150 reviews

Lafontaine Beach Paradise

25 Dec – 1 Jan

$941 NZD per night

Guest favourite

Home in Meaford

4.96 out of 5 average rating, 110 reviews

Close to Hiking & Beach with Large Fenced in Yard

27 Jan – 3 Feb

$279 NZD per night

Guest favourite

Home in Bracebridge

4.93 out of 5 average rating, 340 reviews

Muskoka Hideaway-hot tub/private trails/wood stove

26 Sep – 3 Oct

$559 NZD per night

Guest favourite

Home in Meaford

4.96 out of 5 average rating, 134 reviews

The Meaford Retreat! Beautiful Home on Wooded Lot.

9–16 Oct

$366 NZD per night

Guest favourite

Home in Gravenhurst

4.9 out of 5 average rating, 339 reviews

*Muskoka Bay Resort* All Season Modern Loft 3 Beds

11–18 Sep

$475 NZD per night

Home in Orillia

4.85 out of 5 average rating, 203 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

16–23 Sep

$1,032 NZD per night

Guest favourite

Home in Collingwood

4.87 out of 5 average rating, 133 reviews

JJ’s Collingwood bar & games house.

21–28 Sep

$378 NZD per night

Guest favourite

Home in The Blue Mountains

4.95 out of 5 average rating, 148 reviews

Serene mountainside home View/Shuttle Bus/Pool

3–10 Oct

$708 NZD per night

Pet-friendly home rentals with a pool

Tiny home in Meaford

4.85 out of 5 average rating, 256 reviews

Tiny Home Nestled between Thornbury & Meaford

2–9 Apr

$172 NZD per night

Guest favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

10–17 Dec

$308 NZD per night

Guest favourite

Condo in The Blue Mountains

4.89 out of 5 average rating, 350 reviews

Base of Blue Mountain, Modern Updated Studio

8–15 Jul

$265 NZD per night

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 533 reviews

Treehouse on private, isolated forest (300 acres)

16–23 Feb

$633 NZD per night

Cottage in Lafontaine

4.8 out of 5 average rating, 196 reviews

Beach house (with pool open May-Oct)

25 Oct – 1 Nov

$425 NZD per night

Guest favourite

Apartment in The Blue Mountains

4.89 out of 5 average rating, 674 reviews

Brookside Studio at Blue Mountain - King Bed

9–16 May

$200 NZD per night

Guest favourite

Condo in Oro

4.88 out of 5 average rating, 119 reviews

4-Bed Country Club Haven with Pool, BBQs, and More

14–21 Dec

$354 NZD per night

Chalet in Phelpston

4.88 out of 5 average rating, 283 reviews

Dream Home Oasis; 7 bedroom, Hot Tub Swimming Pool

8–15 Apr

$1,155 NZD per night

Private, pet-friendly home rentals

Guest favourite

Guesthouse in Gravenhurst

4.92 out of 5 average rating, 121 reviews

Waterfront Guest Cabin in Muskoka

27 May – 3 Jun

$350 NZD per night

Guest favourite

Tiny home in Meaford

4.96 out of 5 average rating, 147 reviews

Luxury Vintage Tiny House Farm Stay with Hot tub

26 May – 2 Jun

$347 NZD per night

Guest favourite

Condo in Meaford

4.95 out of 5 average rating, 118 reviews

Steps to Georgian Bay

10–17 May

$212 NZD per night

Cottage in Waubaushene

4.86 out of 5 average rating, 396 reviews

Modern Cottage w/ Hot Tub on Trail - Hike/Run

21–28 Jun

$535 NZD per night

Guest favourite

Loft in Barrie

4.95 out of 5 average rating, 190 reviews

The Penthouse | Luxury at the Lake

28 Jul – 4 Aug

$344 NZD per night

Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

Summer Getaway - 3 min walk to Beach, Clean & Cozy

22–29 Dec

$619 NZD per night

Guest favourite

Tiny home in Mulmur

4.98 out of 5 average rating, 120 reviews

Paradise Pines Bunkie in Woodland Acres

6–13 Oct

$194 NZD per night

Guest favourite

Cottage in Port Carling

4.99 out of 5 average rating, 122 reviews

Lake Muskoka Classic Cottage w/ Hot Tub

4–11 Dec

$1,150 NZD per night

Quick stats about holiday rentals that are pet-friendly in Midland

Total rentals
90 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
2.1K reviews
Nightly prices starting at
$85 NZD before taxes and fees

Destinations to explore