Vacation rentals with a pool in Tiny

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Tiny 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 stars7 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, 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!
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 Oakwood
4.98 out of 5 average rating, 45 reviews

All Season Indoor Pool Escape

ZaeemRating, 5 stars1 month ago
I stayed at Sophia/Shahazad's place over the weekend with my extended family, which includes three toddlers and a newborn. We had an amazing time! Everything was perfect, from the sleeping arrangements to the indoor saltwater pool. We didn't even get to sit outside and enjoy the bonfire or BBQ because we were so busy having fun in the pool and sitting to catch up in the amazing open concept kitchen/dining area. All the bedrooms have full bathrooms, which was huge since we had a family stay in each room and they needed that privacy. We are already looking to come back as soon as possible!
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!

Condo rentals with a pool

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!
Guest favorite
Condo in Innisfil
4.89 out of 5 average rating, 141 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

BallyRating, 5 stars3 weeks ago
Kevin’s place was exceptionally clean and it made our stay very comfortable and relaxing. Everything was walking distance. We would highly recommend Kevin’s place.
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!
Guest favorite
Condo in Blue Mountains
4.83 out of 5 average rating, 270 reviews

Private Backyard/Shuttle/Pool/10min walk 2 village

AliceRating, 5 stars3 months ago
Elyse’s place is lovely! It looks just like the pictures. It was cozy and comfortable during a huge snowstorm. The kitchen is very well quipped. Neighborhood is very pretty and security was visible. Snow was cleared very quickly. Nice proximity to both Blue Mountain and Collingwood. Elyse is a welcoming and very responsive host. Would definitely stay again!

Quick stats about vacation rentals with a pool in Tiny

  • Total rentals

    50 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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