Vacation rentals with a pool in Midland

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Popular amenities for Midland rentals with a pool

House rentals with a pool

Top guest favorite
Home in Mono
4.97 out of 5 average rating, 38 reviews

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars5 months ago
We had an amazing stay! Communication with the hosts was quick, and they were very attentive to all our needs, ensuring we had everything we required. The house was perfectly suited for our group of 8, offering plenty of space and comfort. The property itself is beautiful, with easy access to scenic walks and hikes right on the grounds. Plus, it was just a short drive to Hockley Valley, where we attended our event. This place was ideal for our weekend getaway, and we’d definitely stay here again!
Guest favorite
Home in Orillia
4.96 out of 5 average rating, 25 reviews

Cute and Cozy House

MartinRating, 5 stars3 weeks ago
Anzhelika was a great host. She was very responsive and easy to communicate with. Her place was very nice and convenient for us as we were going to a show at Casino Rama. Would love to come back in the summer to enjoy the pool.
Guest favorite
Home in Utopia
4.86 out of 5 average rating, 43 reviews

Serene Escape: A Nature Getaway

HindRating, 5 stars5 days ago
We had a lovely stay, everything was great. Kitchen was well equipped. Only issue is that there were no towels at all. Which was communicated but we were expecting at least a kitchen rag or hand towels in the washroom.
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 104 reviews

Spacious 4BR Snowbridge Home with Shuttle Access

AleksandarRating, 5 stars1 month ago
Very nice and spacious home with plenty of room for a large group to spread out. Loved the open concept kitchen and dining area and felt plenty close to Blue Mountain village and skiing.
Guest favorite
Home in Port Perry
4.93 out of 5 average rating, 218 reviews

Home away from home with a hot tub and pool

LornaRating, 5 stars4 days 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, 192 reviews

Serene mountainside home View/Shuttle Bus/Pool

LisaRating, 5 stars2 weeks ago
We had a wonderful stay - Brendan's place was clean, organized and in a great area (close to village). Brendan was responsive and helpful and I would recommend this place to relax and enjoy Collingwood.
Guest favorite
Home in Beaverton
4.88 out of 5 average rating, 41 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

AlyssaRating, 5 stars1 month ago
The place was beautiful and the pool was perfect for a winter get-away. They were super responsive the entire time and check-in/out was super easy.
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 months ago
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.

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 stars4 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 stars1 month 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, 244 reviews

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

JillRating, 5 stars6 days 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!
Guest favorite
Condo in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars6 months ago
Kevin was a responsive and friendly host, and his place is clean and comfortable and very close to Friday Harbour. We loved the balcony for breakfast and coffee, and the condo itself was full of friendly folks. We can't wait to go back sometime!
Superhost
Condo in Innisfil
4.91 out of 5 average rating, 139 reviews

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

LoriRating, 5 stars1 month ago
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).
Guest favorite
Condo in Blue Mountains
4.92 out of 5 average rating, 339 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

JamesRating, 5 stars1 day ago
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.
Guest favorite
Condo in Innisfil
4.93 out of 5 average rating, 109 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

ZoyaRating, 5 stars3 months ago
Apartment was even beyond our expectations. It was the most amazing place we have ever rented on New Year holidays. There were 6 people and the place was big and comfortable enough for everybody. Moreover, the apartment was extremely clean and had everything in it to live for short or long terms without any issues. The apartment is located in Friday Harbour which is the perfect place to live in. There are lots of shops, restaurants, a beautiful marina, pool , beach club nearby. We also went for skiing to Horseshoe resort, which took us approx 30 minutes to get there. Shai is a wonderful host, he was in touch during the entire period of our stay in his apartment. He left us a bottle of wine and chocolates as a present, it was so cute. Thank you so much for your attention and care. We will definitely rent your apartment again.
Guest favorite
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, Sleeps 4

SoniaRating, 5 stars7 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

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