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
A community heated outdoor swimming pool is surrounded by lush greenery and a variety of seating options, including blue umbrellas. The clear blue water reflects the sky, creating a serene setting for relaxation. Lounge chairs are positioned along the poolside for guest use.
Home in The Blue Mountains
4.89 out of 5 average rating, 225 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

PamelaRating, 5 stars3 weeks ago
Visited with 4 couples for a few nights away. Beautiful location. Would recommend
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, 220 reviews

Home away from home with a hot tub and pool

CourtneyRating, 5 stars1 week ago
lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot
Guest favorite
Home in The Blue Mountains
4.95 out of 5 average rating, 196 reviews

Pool Open / Serene mountainside home View/Shuttle

TimRating, 5 stars1 month ago
We had a wonderful stay with a family of four including 18 year old teen boys and two dogs. The boys enjoyed the pool table and great tv's while my wife and I enjoyed the great walking and quiet surroundings. It was also easy to have our well trained dogs with us in this location which was wonderful. Thank you Brendan for the terrific stay and allowing us to change our reservation when our plans changed with ease.
Guest favorite
The heated pool is enclosed by a metal fence and features a playful inflatable float. Sun loungers are placed under colorful umbrellas, while a grassy area and trees provide a natural backdrop. A distant view of blue buildings and a hillside completes the scene.
Home in Uxbridge
5 out of 5 average rating, 33 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

SarahRating, 5 stars2 weeks ago
This is a wonderful Airbnb in a really special place away from the hustle and bustle of everyday life. You are in a quiet location within easy access of trails where you can run or walk and if you like to ride, there are plenty of equestrian places providing this facility including part of the Airbnb itself. Youssef and his family were welcoming and on hand to provide advice as needed. That said, they were never intrusive. The accommodation is spacious and homely and you certainly do not feel like rushing out but rather enjoying the facilities. There is everything that you could need for a short or extended stay. Towels were plentiful as were shampoo and lots of extras in the bathrooms and kitchen. The heated pool is a real bonus for children or adults that like a daily swim and although shared with the family, I never felt restricted in its use and loved the fact that it was heated so was comfortable regardless of the external temperature. A wonderful stay and perfect host.
Superhost
Home in Georgina
4.75 out of 5 average rating, 32 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

MeenuRating, 5 stars1 month ago
Myself and my friends had a pleasant staycation at Xin’s house in May. I had given a heads up that there will be a 4 months baby with us and they made sure the entire space is clean making it most comfortable especially for the baby. The host was super responsive from the time I booked and replied to my questions in a timely and respectful manner. Highly recommend to anyone looking for a spot not very far from city yet appreciate a peaceful and relaxing atmosphere.
Guest favorite
The heated pool is framed by a paved patio, featuring several red lounge chairs for relaxation. Lush greenery and shaded areas are visible in the background, complemented by a clear blue sky with scattered clouds.
Home in East Gwillimbury
5 out of 5 average rating, 5 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

AbdulmalikRating, 5 stars1 month ago
This place is the perfect getaway for anyone looking to relax and enjoy quality time with family and friends. Surrounded by beautiful nature and fresh air, it offers a peaceful, private setting that’s ideal for both adventure and quiet moments. I highly recommend it to anyone seeking a refreshing escape.
Guest favorite
An indoor heated pool area is featured, enclosed with high ceilings and large windows. Comfortable seating is arranged nearby, with a minimalist coffee table in the center. A garage-style door allows for an open transition to the outdoors, enhancing the spacious feel of the room.
Home in Beaverton
4.84 out of 5 average rating, 45 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

DarshpreetRating, 5 stars1 week ago
We had an amazing stay at this cottage! Went with both friends and family, and it was the perfect getaway for everyone. The property is beautiful, peaceful, and super well-maintained — exactly what we needed to unwind and enjoy nature. The backyard was great for lawn games, and the indoor space was clean, cozy, and fully stocked with everything we needed. Chris and Rachael were fantastic hosts — super responsive, friendly, and made sure everything was perfect for our stay. You can really tell they care about their guests’ experience. We’re already talking about coming back! Highly recommend this spot to anyone looking for a relaxing escape. Thanks again, Chris and Rachael!
Superhost
Home in Elmvale
4.88 out of 5 average rating, 75 reviews

Ski, Swim, Soak, Boat & Golf

AlyssaRating, 5 stars1 month ago
The cottage is just off the main road making it extremely convenient. There was more than enough space for our party of ten. We really loved the two living spaces, upstairs and downstairs. And the outside area was beautiful. We had a wonderful time. We would definitely recommend Herbs place to friends!

Condo rentals with a pool

Guest favorite
Condo in The Blue Mountains
4.98 out of 5 average rating, 158 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

JohnRating, 5 stars3 weeks ago
Our one night stay at Sabine’s was tremendous. The home is well appointed with plenty of space and easy walking distance to the village. Located in a second floor end unit, it’s a place you immediately feel comfortable in. There is a view of the slopes from the main room picture windows and a small deck area with muskoka chairs. There’s a sizeable fridge to store your beverages to drink while soaking up the views. There are two bedrooms on the main floor, and good sized master in the loft with king bed and en suite. Sabine was very communicative and left detailed instructions. Remote check in was a breeze. There is parking available. I would definitely recommend, and would definitely come back.
Guest favorite
The living area features a comfortable sofa beside a stone fireplace, providing a cozy focal point. A light-toned armchair sits nearby, while a television is mounted on the wall. Natural light enters through the glass door, leading to an outdoor space.
Condo in Oro
4.79 out of 5 average rating, 106 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

DestinyRating, 5 stars2 days ago
Loved our stay here!! Can't say enough positive things about our vacation here. Kitchen was fully stocked, clean bathroom and rooms, easy check in and check out and excellent cooling system as it was a hot few days. Amenities were great and welcoming for families, environment was peaceful and we also loved how the balcony backed onto trees and nature. Would 100% stay here again in the future. Thank you!
Guest favorite
A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.
Condo in The Blue Mountains
4.93 out of 5 average rating, 292 reviews

Cozy Studio Mountainside stay in Blue Mountains

EmmaRating, 5 stars1 week ago
Absolutely Wonderful Stay! I had an amazing stay at John and Kristi’s condo! From the moment I arrived, everything was spotless, cozy, and thoughtfully equipped with everything one could possibly need for a comfortable stay. The attention to detail made it feel like a home away from home. The pool and hot tub area were a real bonus—clean, relaxing, and perfect after a day of exploring. I definitely made the most of it! The location was also ideal, just a pleasant 10-minute walk to the village, which made it easy to enjoy the local shops, restaurants, and atmosphere without needing to drive. John and Kristi were fantastic hosts—friendly, responsive, and clearly committed to creating a great guest experience. I would absolutely stay here again and highly recommend it to anyone visiting the area!
Guest favorite
Condo in The Blue Mountains
4.95 out of 5 average rating, 872 reviews

Stunning Mountain Views- WalkTo Blue, Pool, HotTub

RobertRating, 5 stars2 weeks ago
Enjoyed our family stay with a toddler. Have everything we needed, and easy to access Village area with food + activities.
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, 142 reviews

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

AnisaRating, 5 stars1 month 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
A spacious outdoor pool area is surrounded by lush greenery and comfortable lounge chairs. Umbrellas offer shade over selected seating, while a well-maintained pool invites relaxation. Nearby buildings feature a charming architectural style with multiple stories and large windows.
Condo in The Blue Mountains
4.94 out of 5 average rating, 235 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

CarlyRating, 5 stars1 week ago
Great condo in a perfect location. The location is well stocked and has everything you could need. Walkable to restaurants and the village. Olga was a kind and responsive host. We wouldn’t hesitate to stay here again!
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 Escape, Sleeps 4

SoniaRating, 5 stars9 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 The Blue Mountains
4.93 out of 5 average rating, 230 reviews

Le Petite Chalet - Outdoor Pool / Shuttle to Blue

JesseRating, 5 stars3 weeks ago
A group of four of us stayed here, home felt very spacious, and was nice and tidy. We made use of the free shuttle service to and from Blue Mountain village, which was so easy to navigate, and a quick drive.

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