Vacation rentals with a pool in Simcoe County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Simcoe County rentals with a pool

House rentals with a pool

Guest favorite
A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.
Home in Orillia
4.96 out of 5 average rating, 27 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
A circular above-ground pool is framed by a wooden deck, surrounded by tall trees providing natural shade. Colorful lounge chairs rest on the deck, inviting relaxation. The clear blue water reflects the greenery, creating a serene setting for outdoor leisure.
Home in Utopia
4.87 out of 5 average rating, 47 reviews

Serene Escape: A Nature Getaway

DonnaRating, 5 stars3 weeks 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
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 stars2 weeks ago
Visited with 4 couples for a few nights away. Beautiful location. Would recommend
Guest favorite
A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.
Home in Innisfil
4.92 out of 5 average rating, 48 reviews

2 Bd Boardwalk Condo Patio Oasis

DavidRating, 5 stars1 week ago
Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan
Guest favorite
The exterior of a spacious two-story house features a combination of brick and dark siding. Surrounded by lush greenery, the entryway is adorned with planters and a wooden staircase leading to a welcoming porch, creating an inviting atmosphere.
Home in Waubaushene
5 out of 5 average rating, 13 reviews

GreenDream Estate

AnikaRating, 5 stars2 months ago
We had a fantastic stay at Reza’s cottage! The place was spotless, beautifully maintained, and perfectly equipped for a relaxing getaway. Reza was an excellent host—friendly, responsive, and thoughtful. We truly appreciated his hospitality and attention to detail. Highly recommend this charming cottage for a perfect get away. Can’t wait to visit again! Thank you Reza🙏🏻
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, 92 reviews

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

TessaRating, 5 stars1 month ago
Jerry was very accommodating and fixed any issues promptly. The place is very nice and comfortable for multiple people ….there is space for all. Kitchen has everything you need to cook. Would stay here again for sure. Thank you Jerry,
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 106 reviews

Blue Mountain Retreat w/ Pool + Village Shuttle

AlanaRating, 5 stars1 month ago
We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.
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.

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.
Top guest favorite
Condo in The Blue Mountains
4.93 out of 5 average rating, 523 reviews

*Blue Mountain Village* Walk To Blue, Pool, HotTub

ChristineRating, 5 stars3 weeks ago
Great location, really close to the village, golf, trails and the Scandinave Spa. Condo unit is exactly as advertised with a comfy sofa to lunge on. Beds are comfortable and all linens and needed amenities were easy to find and use.
Guest favorite
A spacious living area features a dark leather sofa complemented by blue accent pillows. A wooden coffee table holds magazines, while a decorative rug covers the floor. The open layout connects to a modern kitchen with white cabinetry, bar seating, and large windows allowing natural light.
Condo in The Blue Mountains
4.93 out of 5 average rating, 149 reviews

Large 3BR Modern Luxury Escape | Walk to Blue

DipalRating, 5 stars2 months ago
It was great staying at Karim’s place. The location is ideal for visiting Blue Mountain with restaurants and grocery stores near by. Also, Karim was very responsive and made sure we had everything we needed.
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
4.94 out of 5 average rating, 298 reviews

Cozy & Charming Retreat at Blue Mountain

GhazalaRating, 5 stars2 weeks ago
Leo and Josie were great! They were friendly and responsive and made sure we had everything we needed for our stay! There were 6 of us and we all had more than enough space. It was a great stay, would definitely recommend! :)
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!
Superhost
An outdoor swimming pool is framed by a stone patio and surrounded by trees. The pool features clear blue water and a shallow entry. A nearby building is visible in the background, while poolside lounge chairs and a nearby fence outline the area.
Condo in The Blue Mountains
4.85 out of 5 average rating, 388 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

KaitlynRating, 5 stars2 weeks ago
Great location, walking distance to Blue Mountain Village! Stephanie was incredibly friendly and helpful with instructions for check-in and check-out. Would absolutely stay here again!
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!

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