Holiday rentals with a pool in Collingwood

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Popular amenities for Collingwood rentals with a pool

House rentals with a pool

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

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars6 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 favourite
Home in Orillia
4.96 out of 5 average rating, 26 reviews

Cute and Cozy House

BobbiRating, 5 stars5 days 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 favourite
Home in Utopia
4.86 out of 5 average rating, 44 reviews

Serene Escape: A Nature Getaway

HindRating, 5 stars2 weeks 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 stars2 months 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 favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 192 reviews

Serene mountainside home View/Shuttle Bus/Pool

LisaRating, 5 stars1 month 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.
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.
Guest favourite
Home in Kimberley
4.88 out of 5 average rating, 198 reviews

Heart of Kimberley - with views and a hot tub

RobinRating, 5 stars1 week ago
Great gals weekend. We really enjoyed the General Store and exploring the area. The house linens were great, beds comfy and the seating areas too :) Weather wasn't conducive to using the outdoor spaces and as older folks we didn't think we'd manage the step stool to get into the hot tub. If there's a next time, we'll try the bustling "Justin's Oven" !!
Superhost
Home in Chatsworth
4.89 out of 5 average rating, 145 reviews

Stonehaven - large country retreat, with pool*

TawnyaRating, 5 stars2 months ago
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!

Apartment rentals with a pool

Guest favourite
Apartment 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 favourite
Apartment 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
Apartment 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 stars2 weeks 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 favourite
Apartment in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars7 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
Apartment in Innisfil
4.91 out of 5 average rating, 140 reviews

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

LoriRating, 5 stars2 months 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 favourite
Apartment in Blue Mountains
4.92 out of 5 average rating, 340 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

JamesRating, 5 stars1 week 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 favourite
Apartment in Innisfil
4.93 out of 5 average rating, 111 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

AlinaRating, 5 stars1 week ago
Shai was a wonderful host — everything was great from start to finish! The place was clean, comfortable, and exactly as described. Highly recommend!
Guest favourite
Apartment in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, 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 holiday rentals with a pool in Collingwood

  • Total rentals

    110 properties

  • Nightly prices starting at

    £15 before taxes and fees

  • Total number of reviews

    880 reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

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