Vacation rentals with a pool in East Gwillimbury

Find and book unique homes with a pool on Airbnb

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Popular amenities for East Gwillimbury rentals with a pool

House rentals with a pool

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 stars4 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
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, 49 reviews

2 Bd Boardwalk Condo Patio Oasis

JoannRating, 5 stars1 day ago
We really enjoyed our stay at Friday Harbour so much so I think we’re gonna be coming back again next year thank you again so much!!!
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, 95 reviews

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

DianeRating, 5 stars1 week ago
This house was perfect for our large group: for couples and a baby. Having the pool was a bonus that we really appreciated in the warm weather. The kitchen was extremely well equipped, and there were enough linens as well as pool towels for us all. There was plenty of space for everybody as the rooms were all quite large, particularly the master bedroom. The house were incredibly accommodating when we realized after checkout that we had left a couple of items behind. They were able to make arrangements for us to retrieve them several days later back in Toronto! I definitely can recommend this house.
Guest favorite
Home in North York
4.85 out of 5 average rating, 75 reviews

Toronto Pool Retreat

JasonRating, 5 stars4 weeks 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.
Guest favorite
An above-ground pool with a wooden deck is positioned in a grassy area, bordered by reeds and a tranquil body of water. Two metal ladders are attached to the pool, and multiple chairs and storage items are visible nearby, suggesting a relaxed outdoor setting.
Home in Elmvale
4.89 out of 5 average rating, 19 reviews

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago
We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.
Superhost
Home in Mimico-Queensway
4.87 out of 5 average rating, 46 reviews

private backyard SPA oasis in Toronto

WadeRating, 5 stars2 weeks ago
Awesome 👌 property with above average amenities and spa style options available; the hotubs alone were top notch, clean, hot and easy to use. The house itself was beautiful, well laid out and very clean. anither great property if anyone is looking to be in the mix of it all plus having the extras in your own back yard.
Superhost
An outdoor space features a spacious deck with a comfortable seating area and an umbrella. A saltwater pool with lounge chairs and elegant landscaping is visible in the background, surrounded by mature trees. String lights add a welcoming touch to the atmosphere.
Home in Central Etobicoke
4.89 out of 5 average rating, 9 reviews

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

TanyaRating, 5 stars9 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.
Guest favorite
The exterior of a Victorian-style home is framed by lush greenery. The exposed brick facade is complemented by vertical vines climbing the walls. Windows with white trim are positioned symmetrically, allowing natural light to enhance the inviting appearance of the house.
Home in Niagara
4.91 out of 5 average rating, 304 reviews

King West Victorian Studio Gem

TamerRating, 5 stars5 days ago
It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.

Condo rentals with a pool

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 stars3 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
The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.
Condo in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars3 months ago
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!
Guest favorite
A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.
Condo in Mississauga
4.88 out of 5 average rating, 176 reviews

Beautiful Penthouse with Breathtaking View

JamesRating, 5 stars1 week ago
Wafa was an incredible host and was always responsive and attentive to any questions we had. The place was just as described, clean, and had a wonderful view. Would definitely book again!
Guest favorite
An outdoor pool area features a large rectangular pool surrounded by lounge chairs and umbrellas. Several guests are seen enjoying the water, along with sunbathers on the deck. Modern condominiums provide a backdrop with various levels of outdoor space, enhancing the recreational atmosphere.
Condo in Toronto
4.93 out of 5 average rating, 152 reviews

Hidden gem in Humber bay shores Toronto w/ parking

RebeccaRating, 5 stars1 month ago
Super convenient area for getting around the city. Very clean and super friendly host.
Guest favorite
A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.
Condo in Mississauga
4.84 out of 5 average rating, 268 reviews

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

VerdiRating, 5 stars3 weeks ago
Great place , easy to find and there are many great things to do in the area , and the view front the condo was just beautiful..
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
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
The indoor saltwater pool area features large windows allowing for natural light to flood the space. The pool is bordered by tile flooring with safety signage visible. Minimalistic design elements include sleek lines and modern lighting, creating a contemporary swimming environment.
Condo in Davisville Village
4.93 out of 5 average rating, 269 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

JimRating, 5 stars1 week ago
Judy's one bedroom apartment felt like a home away from home. We never heard our neighbors or any disturbing sounds through the walls. The other residents of the building were friendly and helpful. The property is an easy five-minute walk from the subway and buses. We were able to visit all the Toronto destinations on our list, then we could retreat to this haven in the sky. The bed was very comfortable. There were plenty of bed and bath linens. The kitchen included all we needed to cook and dine. It would have been handy to have more regular-size spoons and forks. We enjoyed a swim in the pool and a soak in the hot tub.

Quick stats about vacation rentals with a pool in East Gwillimbury

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$6,280 GYD 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, Metro, and SilverCity Newmarket Cinemas

Destinations to explore

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