Vacation rentals with a pool in Lake Simcoe

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake Simcoe

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.

Home in Barrie

4.92 out of 5 average rating, 90 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

Superhost

A heated in-ground pool is surrounded by a stone patio featuring a natural stone waterfall. A hot tub is positioned nearby, and a BBQ area with seating is visible. A wooden pergola offers shade in the outdoor space, which is enclosed by a wooden fence.

Vacation home in Port McNicoll

4.9 out of 5 average rating, 10 reviews

Executive vacay, sauna, heated pool, hottub, lake!

In the cusp of the Georgian bay, this large, detached house is custom & newly built, equipped with a heated sports pool (hot tub open all year), 5 bedrooms, Big screen TVs, IPTV, bar, laundry, high speed internet, kitchens, BBQ, fire pit, sauna, Foosball, bikes +more amenities & areas to entertain. Close to epic trails, beaches, lakes, and all of Georgian bay's features-close to stores. Perfect for families or small groups. Mature, respectful crowd, NO PARTIES, Covid cleaning A+, pets ask :)

Guest favorite

A modern swimming pool area is surrounded by sunny greenery and features a large glass wall of the nearby building, giving a bright and open feel. Lounge chairs are positioned nearby, inviting relaxation by the water.

Condo in Oro

4.87 out of 5 average rating, 89 reviews

Hillside Haven: Serene Studio Retreat for 4

Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Guest favorite

This aerial view captures a charming multi-unit building covered in snow, bordered by a wintry landscape. In the background, ski slopes are visible, emphasizing the winter setting. The two-story structure features a combination of pastel colours and multiple balconies, enhancing the inviting atmosphere of the resort.

Condo in The Blue Mountains

4.81 out of 5 average rating, 149 reviews

Rivergrass Hot Tub, Pool, Clean, Lovely, Great Loc

This beautiful private two bedroom condo is in the incredible Rivergrass Resort, right across from the Village. It sleeps four comfortably and you’ll be a short walk to the to the hills and in the center of everything Blue Mountain has to offer. Guests adore this condo’s stylish furnishings hotel amenities including a four-season hot tub and seasonal pool, private patio with gas BBQ, and three TVs with cable and streaming services. This condo is ideal for couples, friends, and families!

Superhost

Home in The Blue Mountains

4.89 out of 5 average rating, 220 reviews

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd

Imagine a super large, cozy vacation home nestled in the heart of Blue Mountain Ski Resort, offering a perfect blend of luxury and comfort. Four bedrooms with 2 King beds. This expansive retreat boasts multiple levels thoughtfully designed to provide the utmost relaxation and tranquility. The home features 4.5 spacious bathrooms. Our Sauna and Entertainment basement is ready for guests' enjoyment. Walk to the Village or take a Free Shuttle Bus. Walk to Pool in 1 minute from our home.

Guest favorite

Condo in The Blue Mountains

4.98 out of 5 average rating, 151 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (seasonal and closes Sept 3) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

Top guest favorite

Condo in Innisfil

5 out of 5 average rating, 9 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

A sun-drenched patio and corner unit, our space is professionally designed and located in the heart of Friday Harbour close to all attractions. Our place features: → Free secured parking for 1 car → Keyless 24HR self check-in → Over 800 ft² of space → Building features hot tub and pool → 2 stylish and separated bedrooms with comfy mattresses → Close to all Resort features - beach, harbour, golf, restaurants Only an hour north of Toronto, and 20 minutes from Barrie. Come and enjoy!

Superhost

Cabin in Fergus

4.88 out of 5 average rating, 106 reviews

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

Guest favorite

An indoor heated pool is featured, surrounded by wooden paneling and large windows that provide natural light. A comfortable seating area is positioned nearby, along with exercise equipment visible in the background. The clean water reflects the light, enhancing the serene ambiance.

Cottage in Baysville

4.94 out of 5 average rating, 108 reviews

Muskoka Forest Chalet with a Private Indoor Pool

Welcome to the beautiful Muskoka Forest Chalet. Equipped with a private indoor pool, wood burning fireplace, home gym, fully stocked kitchen, theatre room, new modern furnishings and much more. Escape the city life with a one-of-a-kind recently upgraded cottage. Whether you are coming with family or friends, our cottage provides a fun and relaxing experience for every guest. Enjoy activities nearby including ice fishing, hiking, snowmobile trails or shopping and dining

Guest favorite

Townhouse in Wasaga Beach

4.91 out of 5 average rating, 176 reviews

Scenic WasagaBeach seasonal HeatedPool FireplaceAC

Explore Wasaga Beach right on the shores of Georgian Bay with newly upgraded townhouse, heated seasonal pool, BBQ, outdoor fire pit and grassy play area. Situated right on Beach 4. Relax at the fire pit, stroll the beach, enjoy the fresh air and peaceful scenery. Upper level two bedrooms (sleeps 6). Master BR overlooks beach with gorgeous view of bay and sunset. Main floor kitchen/breakfast area/large TV Winter Activities Blue Mountain Village & Ski Hill Nordic Trail

Guest favorite

A hot tub is set within a landscaped area, featuring a shallow section marked at 0.91 meters. Wooden slats create shade overhead, while sunlight creates patterns on the tiled surface. Surrounding greenery and nearby building facades enhance the tranquil environment.

Apartment in Innisfil

4.96 out of 5 average rating, 27 reviews

Modern Luxury Delight with a Pool and Hot Tub

Welcome to the Highpoint Condo. This 2 bed / 2 bath third floor suite has a beautiful view of the Pool and Hot Tub. Based in a prime location, this suite is the ideal place to unwind and take in the stunning views of the pool and hot tub. It's the perfect spot to start your day with a cup of coffee or end it with a glass of wine. Look forward to just lounging, sunbathing, or dining al fresco. Come and enjoy this unique and tranquil getaway.

Guest favorite

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. A living area boasts modern furniture, including a sofa and seating around a fire pit. The outdoor pool area is highlighted, alongside the exterior view of the building, showcasing multiple levels.

Home in Innisfil

4.88 out of 5 average rating, 180 reviews

King Bed*Pool*Fireplace*BBQ*Smart TV

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen