Vacation rentals with a pool in Midland

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Top-rated rentals with a pool in Midland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
5 out of 5 average rating, 201 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Top guest favorite
Townhouse in Port Severn
4.99 out of 5 average rating, 212 reviews

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.

Top guest favorite
A cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.
Apartment in Blue Mountain Resort Area
4.91 out of 5 average rating, 178 reviews

Blue Mountain Studio Retreat

Our cozy studio is located at the base of Blue Mountain at the North chair lift, with ski in / ski out access. Perfect for 2 or a couple with small children, this newly renovated Studio has 1 bedroom, 1 bathroom and sofa bed; fully stocked kitchen, electric fireplace and flat screen T.V. Only 1 km from the Village with many restaurants, shopping and activities. Enjoy a short trip to the Scandinavia Spa or many close by beaches. Blue Mountain is a great place for the whole family to enjoy.

Guest favorite
Cottage in Tiny
4.97 out of 5 average rating, 149 reviews

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.

Superhost
An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.
Condo in Oro
4.79 out of 5 average rating, 140 reviews

Hillside Haven: Serene Studio Retreat for 4

Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Guest favorite
A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.
Home in Shanty Bay
4.85 out of 5 average rating, 109 reviews

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

Superhost
An open living space is displayed, featuring a comfortable sofa adorned with throw pillows. A central coffee table rests atop a patterned area rug, while a wooden dining table with seating for six is visible. The kitchen area is positioned at the back, showcasing modern appliances.
Condo in Oro
4.88 out of 5 average rating, 99 reviews

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!

Superhost
A spacious bed is centered in the room, adorned with a decorative throw pillow. Nightstands are positioned on either side, each featuring a lamp that casts a soft glow. Framed artwork enhances the wall above the bed, contributing to a calming atmosphere.
Condo in Oro
4.74 out of 5 average rating, 325 reviews

Cozy Deluxe Studio 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!

Guest favorite
Home in Blue Mountain Resort Area
4.89 out of 5 average rating, 116 reviews

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.

Guest favorite
A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.
Cottage in Wasaga Beach
4.94 out of 5 average rating, 300 reviews

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.

Top guest favorite
A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.
Condo in Oro
4.95 out of 5 average rating, 176 reviews

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!

Guest favorite
Cottage in Lafontaine
4.84 out of 5 average rating, 271 reviews

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

Quick stats about vacation rentals with a pool in Midland

  • Total vacation rentals

    Explore 10 vacation rentals in Midland

  • Nightly prices starting at

    Midland vacation rentals start at G$10,464 GYD 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 vacation 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

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