Vacation rentals with a pool in Midland

Find and book unique homes with a pool on Airbnb

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Popular amenities for Midland rentals with a pool

House rentals with a pool

Guest favorite
Home in Orillia
4.96 out of 5 average rating, 26 reviews

Cute and Cozy House

BobbiRating, 5 stars1 month ago
After being displaced from our home after damage from severe weather we were so fortunate to find this location. The house accommodated our family of 4 with pets for nearly a month without any issues. The kitchen is well equipped, bathrooms are well finished, bedrooms were comfortable and the location was very clean. The backyard is a beautiful and relatively private space hidden within a 15 minute walk to the downtown restaurants or the beach area. Anzhelika is an excellent host who was very responsive when needed, provided clear instructions and ample privacy. We would happily recommend this location to friends and family attending the area for events.
Guest favorite
Home in Utopia
4.87 out of 5 average rating, 47 reviews

Serene Escape: A Nature Getaway

DonnaRating, 5 stars1 week ago
I rented the villa for a group of 16 ladies for a golf getaway. The owners are excellent to communicate with and responded immediately to any questions or issues we had during and before our stay. The villa was spacious and well equipped with dishes ect to accommodate a large group. Beds comfortable. Unfortunately due to the weather the pool was not opened but some enjoyed the hot tub. Grounds looked like the would be very nice but again due to weather grounds we’re not manicured and grass has not been cut. Would definitely book again and hopefully next time enjoy the outdoor area. Thks for having us
Guest favorite
Home in Barrie
4.92 out of 5 average rating, 91 reviews

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

ShrutiRating, 5 stars1 month ago
We had a wonderful stay in this beautiful house. We booked it for a small get-together with our friends. The house is spacious and beautifully decorated. Jerry made sure everything was set up to make our stay comfortable. Although the pool wasn’t open during our visit, it’s definitely something we’re looking forward to next time. We are glad we chose this place. Thanks again for hosting us!
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 106 reviews

4BR Family Home w/ Pool Access + Village Shuttle

AlanaRating, 5 stars3 weeks ago
We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.
Guest favorite
Home in Port Perry
4.93 out of 5 average rating, 219 reviews

Home away from home with a hot tub and pool

LornaRating, 5 stars1 month ago
Had a great time at Angie's place! Everything was very clear, clean and easy—instructions were left out and amenities were provided. The hot tub was a great bonus to the weekend. We even had a delayed car picking us up, and Angie was very accommodating and understanding about letting us stay slightly longer while waiting for its arrival.
Guest favorite
Home in The Blue Mountains
4.95 out of 5 average rating, 195 reviews

Pool Open / Serene mountainside home View/Shuttle

KimberleyRating, 5 stars4 weeks ago
Thank you Brendan for a wonderful stay in your beautifully decorated and very clean townhouse in Blue Mountain!! We had a wonderful time celebrating my Mom’s 80th birthday! It felt very comfortable and spacious for our small group. The shuttle to and from the village was on time and friendly - we also walked there too during the day. Excellent customer service and amenities. I highly recommend. Thanks again!
Superhost
Home in Orangeville
4.64 out of 5 average rating, 14 reviews

Private cottage heated pool/HotTub/Games 20 Acre

KyleRating, 5 stars2 weeks ago
Stayed here for a few days for a work retreat. Place was great for what we needed. Tons of space and a very pretty location on a quiet country road. A few issues with the amenities - bbq didn’t work well, the hot tub was pretty green, and the dishwasher was temperamental, but when we reached out, they sent someone over to address it right away. Overall, it was exactly what we needed and we had a great stay - would definitely recommend/come back!
Guest favorite
Home in Beaverton
4.86 out of 5 average rating, 43 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

Jo AnnRating, 5 stars1 month ago
Had a fantastic stay. All the little extras for the kids were a great surprise. The whole family enjoyed it very much.

Condo rentals with a pool

Guest favorite
Condo in The Blue Mountains
4.85 out of 5 average rating, 141 reviews

Large, luxury, upper floor condo, steps to Village

MatthewRating, 5 stars5 months ago
Excellent place by a fantastic host. The place was clean, well located and has everything you would need such as kitchen utensils, games + TV, and plenty of clean quality towels. Ulana and Amir were also very friendly and responsive. We enjoyed our stay a lot.
Guest favorite
Condo in The Blue Mountains
4.91 out of 5 average rating, 111 reviews

The Fairway Chalet

SathishRating, 5 stars2 months ago
From the initial booking confirmation to the final checkout, the hosts were absolutely outstanding! They provided clear and detailed directions to the property, and the space was impeccably clean upon our arrival. The rooms were cozy and well-maintained, and the kids especially loved their room. Overall, it was a delightful and memorable stay at Blue Mountain.
Superhost
Condo in The Blue Mountains
4.86 out of 5 average rating, 245 reviews

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

JillRating, 5 stars1 month ago
Rosa’s was exactly as advertised. It was lovely and quiet and perfect for our trip to collingwood with our dog. We would definitely stay again!
Superhost
Condo in Innisfil
4.91 out of 5 average rating, 142 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

AnisaRating, 5 stars2 weeks ago
My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!
Guest favorite
Condo in Blue Mountains
4.92 out of 5 average rating, 341 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Vijay BalajiRating, 5 stars1 month ago
Great place and fantastic hosts! We truly enjoyed our stay here. The sound of the stream was very relaxing when we sat out in the patio. The upper level has a nice view of the lake too!
Guest favorite
Condo in Innisfil
4.93 out of 5 average rating, 112 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

Michella,BibianRating, 5 stars2 weeks ago
We had an amazing stay. Everyone loved it and enjoyed the house. Very welcoming and well done. There were board games etc, beds were very comfortable and he was the only one who provided early check after 10 am in check out after at 5 pm. That was so helpful and gave us more time together.
Guest favorite
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

SoniaRating, 5 stars8 months ago
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive
Guest favorite
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars11 months ago
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Quick stats about vacation rentals with a pool in Midland

  • Total rentals

    30 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    480 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Midland
  6. Rentals with pools