Vacation rentals with a pool in Lake Simcoe

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lake Simcoe rentals with a pool

House rentals with a pool

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 favorite
An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.
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 stars1 week 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.
Top guest favorite
A private heated pool is framed by stone tiles and lush greenery, reflecting sunlight. Large glass doors lead into the home, enhancing the outdoor connection. Seating areas are available nearby, surrounded by natural landscaping and elevated steps leading to the indoor space.
Home in Toronto
4.99 out of 5 average rating, 143 reviews

Heated Pool-tub Open 365 Days

PatrickRating, 5 stars1 day ago
We came up for a concert for the night and it was a great experience. The pool and hot tub were a wonderful perk and very well maintained and nice. The house is beautiful and spacious. Miles was extremely accommodating, we needed to get there a little early to help with making the concert on time and it was no problem at all. He worked with us and when there was an issue with the internet. he came and fixed it in person. The location is killer too! I strongly recommend staying here, it was a wonderful experience in every way!
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 stars3 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.
Superhost
A private heated pool is surrounded by a patio featuring red lounge chairs and a small green table. Lush greenery borders the pool area, providing a sense of privacy. A shed is visible in the background, and clear blue skies complete the serene outdoor setting.
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.
Superhost
A spacious backyard features a heated saltwater pool surrounded by a manicured lawn, mature trees, and lounge chairs. A deck extends from the house, providing a view of an outdoor dining area. Sunlight filters through the foliage, creating a bright atmosphere.
Home in Toronto
4.89 out of 5 average rating, 9 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

TanyaRating, 5 stars8 months ago
We had a great time at Bessa’s. The house was beautifully decorated. The pool and back yard were amazing. We will definitely be back. I would highly recommend staying here.
Superhost
Home in Pickering
4.85 out of 5 average rating, 46 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Huy LongRating, 5 stars1 month ago
Great host! Great response time and services!
Guest favorite
Home in Buckhorn
4.97 out of 5 average rating, 91 reviews

Blue Haven *Saltwater, Indoor Pool & Hot tub*

CristinaRating, 5 stars1 week ago
This was a lovely private getaway for the family. The kids enjoyed the pool and the bunk beds. Felt very cozy with nice personal touches like bathrobes, loads of clean towels, board games and several kitchen appliances to choose from. House was very clean and kids felt right at home. Thank you for the hospitality!

Condo rentals with a pool

Guest favorite
An indoor pool area is visible, featuring a large, rectangular pool surrounded by tiled flooring. Floor-to-ceiling windows allow natural light to fill the space. Lounge chairs are positioned along the edges, and a seating area can be seen in the background.
Condo in Toronto
4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

StephanieRating, 5 stars1 month ago
Jessica was one of the best Airbnb hosts I’ve had in a long time! I celebrated my three-year anniversary here with my partner, and it was absolutely perfect. Jessica went above and beyond by setting up the room beautifully with flowers, rose petals, and electric candles—my partner was overjoyed. She was incredibly accommodating, allowing us to check in early and responding quickly to all my requests. The space itself was spotless, smelled amazing, and was incredibly comfortable. As a same-sex couple, safety is always a consideration when booking accommodations, but this location felt extremely secure. My partner and I were out late at night and felt completely at ease. The apartment has a double lock for added security, and the building itself is well-monitored. On top of all that, the view of downtown and the CN Tower was stunning. I highly recommend this stay, especially for couples—10/10!
Top guest favorite
Condo in Toronto
5 out of 5 average rating, 46 reviews

Prime location • Amazing views • FREE parking

LatishaRating, 5 stars1 week ago
Radmir was an excellent host. Great getaway it was peaceful. It was private. It was convenient so many restaurants around everybody so nice everybody so pleasant the environment was clean. It felt like a home away from home. Great experience for my first time in Toronto Canada.
Guest favorite
A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.
Condo 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
The image showcases a spacious outdoor area featuring a swimming pool surrounded by landscaped gardens. Modern buildings with balconies are visible in the background. Seating areas with tables and chairs are arranged around the pool, providing a relaxed atmosphere for guests.
Condo in Innisfil
4.91 out of 5 average rating, 139 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 favorite
A serene bedroom is illuminated by city lights visible through large windows. The bed is neatly made, and a dresser appears nearby. Beautifully draped curtains gently frame the view, enhancing the tranquil setting at night.
Condo in Toronto
4.88 out of 5 average rating, 32 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

JordanRating, 5 stars3 weeks ago
Great condo in a great location. Lovely view of Toronto. Walking distance to all amenities.
Guest favorite
Condo 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 favorite
An outdoor pool area features a modern design with lounge chairs positioned along the water's edge. A wooden pergola provides shaded seating. Surrounding greenery and contemporary building façades enhance the space, creating a relaxing setting for guests.
Condo in Innisfil
4.93 out of 5 average rating, 110 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

shawnaRating, 5 stars1 week ago
Shai was a great host. It is a beautiful location. We loved that there was a late check- out for 5 pm. I would definitely come back to stay.
Guest favorite
The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.
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

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