
Holiday rentals with a pool in Midland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Midland
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Pool, Wifi, Free parking, Golf, FIFA, Laundry, BBQ
Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

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.

Oasis Spa w/ Private Sauna!
Welcome to Our Unique Group of Spa Getaway Suites at Friday Harbour Resort - The Oasis Spa Getaway Rejuvenate, Relax & Unwind with your own private in-suite Sauna and Stunning patio Bamboo Oasis with fire table and Weber BBQ overlooking the pool & hot tub Reconnect with your loved one in our most tropical & romantic suite with multiple fire elements and fully stocked chefs kitchen Professionally designed to take your breath away, a luxury experience to make memories that last a lifetime!

Lovely king size room with kitchenette
An inviting four-season natural playground surrounded by rolling hills and forested trails is located in a spectacular country setting. The Mount St. Louis Moonstone Ski Area is 12 km away, Barrie is 25 km away, and Toronto is 138 km away. Onsite amenities include a pool, fitness center, fire pit, and play area. Nearby, you can enjoy an array of fun attractions and activities for every season! Several convenient perks are available to provide you with the best and most comfortable stay.

King Bed, Pool, Gym, Ravine View, Your Getaway!
Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

Stunning Suite in Horseshoe Valley
Sitting on top of Horseshoe Valley, this stunning and unique condo sets the stage for a memorable and cozy trip. This suite has it all! - Fully stocked kitchen - 6-person dining table - Pull-out couch + loveseat + lounge chair - Cozy fireplace - Comfortable king-size bed - 2-person soaker tub + shower - Private Balcony - Year-round indoor/outdoor pool with hot tub and sauna - Fully equipped gym Minutes away from Vetta Spa, Horseshoe Valley, golf courses and more!

Spacious 1-br w jacuzzi at Horseshoe Valley
Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Rivergrass Oasis Across from Blue Mtn Hot Tub!
Rivergrass Oasis is located in the Beautiful Rivergrass community adjacent to Blue Mountain. This unit backs onto Monterra Golf Course, the community swimming pool and hot tub. This unit is within a 5-7 minute walk to the heart of Blue Mountain Village and Monterra Golf Course. Making this property an ideal location for those that want to park their car and walk to the all amenities at Blue Mountain such the ski hills, restaurants, shops, and activities.

Spacious Hideaway in Nature
Welcome to the charming Shanty Bay area! Embrace the relaxed vibes surrounded by natural beauty. Enjoy leisurely walks by Lake Simcoe or explore nearby parks like Oro-Medonte Rail Trail. Discover local shops and eateries, or indulge in water activities and outdoor adventures. Our cozy Airbnb accommodates 4 guests, with a king-size bed and comfy couches. Experience the best of both worlds - a laid-back getaway and exciting local attractions.

GATED RESORT COTTAGE
[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

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!

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.
Popular amenities for Midland rentals with a pool
House rentals with a pool

Cute and Cozy House

Cozy Corner Townhome | Shuttle To The Village

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

Our vacation home. Fully equipped. Pool. Fire Pit.

Blue Mountain Retreat In Historic Snowbridge

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Serene mountainside home with View/Shuttle Bus

Blue Mountain Village Townhome 4 Bedroom w Shuttle
Condo rentals with a pool

Lovely 3 Bedroom Condo with Stunning View and Pool

Blue Mountain Getaway at North Creek Resort

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

Blue Mountain condo in Historic Snowbridge

Clearview Chalet • Modern 3BR • Mountain Stay

Exceptional 2+1 ground floor condo @Friday Harbour

The Blue Mountain's Dream Escape | Pool | Hot Tub

Private Backyard/Shuttle/Pool/10min walk 2 village
Other holiday rentals with a pool

Oasis of luxury: 1 bdrm retreat w/Hot Tub Access

1BR Friday Harbour Retreat | Balcony + Pool Access

Large Resort Studio Suite Near Horseshoe

Stylish 1 bedroom Pet friendly Condo by Sage Homes

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Sweet Memories of Georgian Bay

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

Spacious King Studio w/ pool, hot tub, kitchenette
Quick stats about holiday rentals with a pool in Midland

Total holiday rentals
Explore 10 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $70 AUD per night before taxes and fees

Verified guest reviews
Over 380 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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

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

4.6 Average rating
Midland stays receive an average rating of 4.6 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
- Detroit Holiday rentals
- Mont-Tremblant Holiday rentals
- Cabin rentals Midland
- Family-friendly rentals Midland
- Apartment rentals Midland
- Rentals with a hot tub Midland
- Fitness-friendly rentals Midland
- Rentals with a fire pit Midland
- Beachfront rentals Midland
- Rentals with a patio Midland
- Waterfront rentals Midland
- Rentals with outdoor seating Midland
- Rentals with beach access Midland
- Cottage rentals Midland
- Rentals with lake access Midland
- House rentals Midland
- Rentals with a kayak Midland
- Pet-friendly rentals Midland
- Rentals with a fireplace Midland
- Rentals with an EV charger Midland
- Rentals with a washing machine and dryer Midland
- Rentals with pools Simcoe County
- Rentals with pools Ontario
- Rentals with pools 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
- Burl's Creek Event Grounds
- Bass Lake Provincial Park
- Mono Cliffs Provincial Park
- Casino Rama Resort
- Wye Marsh Wildlife Centre
- Innisfil Beach Park
- Awenda Provincial Park
- Orillia Opera House
- Couchiching Beach Park
- Centennial Beach
- Menominee Lake




