Vacation rentals with a pool in East Gwillimbury

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Popular amenities for East Gwillimbury 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, 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
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 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
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, 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
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, 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
The exterior of a spacious estate property is showcased, featuring a two-story façade with a mix of brick and siding. The entryway is framed by a covered porch. Lush green lawns and mature trees are visible, enhancing the tranquil outdoor setting.
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!
Top guest favorite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in The Beaches
4.99 out of 5 average rating, 147 reviews

Heated Pool-tub Open 365 Days

MinnieRating, 5 stars1 week ago
Miles is a fantastic host! Not only was he proactive in communicating details regarding entry and amenities, he went above and beyond with little fresh baked goods, Smart Home instructions guide, and providing literally everything you'd need to feel at home (bathrobes, teas, serving dishes+several cups, even milk and cream in the fridge!) The Hot tub was great, the place was spotlessly clean, and the balcony views were a pleasure to enjoy. This is a great house with lovely sky lights in the kitchen and beautiful location right by the boardwalk! 11/10 ✨
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
4.86 out of 5 average rating, 43 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

Jo AnnRating, 5 stars1 month ago
Had a fantastic stay. All the little extras for the kids were a great surprise. The whole family enjoyed it very much.
Guest favorite
Home in North York
4.86 out of 5 average rating, 74 reviews

Toronto Pool Retreat

JasonRating, 5 stars1 week ago
Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.

Condo rentals with a pool

Top guest favorite
A sleek hot tub is located under a wooden pergola, with the surrounding patio area featuring modern seating arrangements. Bright sunlight streams in, highlighting the contemporary architecture of nearby buildings, while potted plants add a touch of greenery to the space.
Condo in Innisfil
5 out of 5 average rating, 10 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

ConradRating, 5 stars2 months ago
Franco and his team are lovely to deal with. They are extremely communicative and in a timely manner. The apartment is exactly “like” the pictures shown, warm, cozy and overall a very welcoming home. In addition, to having such a wonderful place to stay in, they have thought of every kitchen tool you may need during your stay, it’s great to have access to all these accessories. Thank you for the great stay, I would definitely recommend your place to anyone staying in the area.
Top guest favorite
A living area features two brown leather sofas positioned near large windows, offering a view of the downtown skyline. A floor lamp stands beside a decorative bench, and two floral paintings adorn the wall, adding a touch of elegance to the modern space.
Condo in Downtown Toronto
5 out of 5 average rating, 48 reviews

Prime location • Amazing views • FREE parking

kiran Rating, 5 stars1 week ago
Radmir was very communicative right from the moment I booked his place. He truly went above and beyond to meet our needs all along the way. We felt at home and were blown away by his hospitality. Great apartment with all necessary amenities. The pots and pans in his kitchen are top notch. The view from the apartment is breathtaking. The location unbeatable - right next to the aquarium, CN tower, Rogers Center and many other things. The building is very secure and the front desk personnel were very nice too. The pool is great with nice gazebo style seating and has a wonderful view of the CN tower. all in all I would highly recommend this host and place. We would love to rent this place again on our next visit to Toronto. Thanks Radmir!
Top guest favorite
A chic living area features a gray chaise sofa adorned with pastel pillows, complemented by light pink curtains. A marble-top dining table sits near a flat-screen TV mounted on the wall, while a decorative bowl adds a touch of elegance to the coffee table.
Condo in Fort York
4.98 out of 5 average rating, 191 reviews

Stylish Downtown Toronto Condo with Free Parking

DarrenRating, 5 stars6 days ago
Great location and amenities, fantastic host - would gladly stay again
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 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!
Superhost
A modern kitchen area features sleek cabinetry and stainless-steel appliances, with an illuminated bar counter offering seating for two. Large windows provide expansive views of the city skyline at dusk, as warm lights from distant buildings create a vibrant evening atmosphere.
Condo in Fort York
4.77 out of 5 average rating, 35 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

JordanRating, 5 stars1 month ago
Great condo in a great location. Lovely view of Toronto. Walking distance to all amenities.
Guest favorite
An indoor pool area showcases a clear blue water surface, illuminated by natural light streaming through large floor-to-ceiling windows. The pool's shallow area is marked with a clear indication, and wooden benches are positioned along the walls, providing a place for relaxation.
Condo in Fort York
4.86 out of 5 average rating, 246 reviews

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

MikeRating, 5 stars1 week ago
When travelling you do your best to have as much as possible in your control so when things go wrong you minimize the damage. Having a responsive proactive host to accomadate these moments makes life much easier. Cheers to Emmanuel 🔥
Superhost
A modern two-story townhouse complex is presented, featuring balconies with comfortable seating. Above the outdoor pool, laundry items are displayed on a clothesline. A well-maintained grassy area surrounds the pool, providing a relaxing atmosphere for guests.
Condo in Wasaga Beach
4.91 out of 5 average rating, 79 reviews

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking

RukshanRating, 5 stars5 months ago
We had a wonderful and pleasant stay! The host was very responsive and made sure we had everything we needed. The place was clean, comfortable, and welcoming. We’re already planning to come back again. Highly recommend!
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 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

Quick stats about vacation rentals with a pool in East Gwillimbury

  • Total rentals

    10 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    120 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Costco Wholesale, Brooks Farms, and SilverCity Newmarket Cinemas

Destinations to explore

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