Vacation rentals with a pool in East Gwillimbury

Dome in Bradford West Gwillimbury

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

4.96 out of 5 average rating, 383 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

An aerial view captures the layout of Friday Harbour, featuring an expansive marina surrounded by lush greenery and residential buildings. The coastline, with a sandy beach and ample water access, provides recreational opportunities. The serene water reflects the natural beauty of the surrounding landscape.

4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina, while lounging or eating outside.

4.95 out of 5 average rating, 105 reviews

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Scarborough

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

4.98 out of 5 average rating, 555 reviews

A serene pond is visible, with a person kayaking on calm waters. A wooden dock is in the foreground, featuring two white lounge chairs and a blue float. Lush greenery surrounds the pond, complementing the tranquil atmosphere.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

An outdoor pool area features a modern design with lounge chairs positioned along the water's edge. A wooden pergola provides shaded seating. Surrounding greenery and contemporary building façades enhance the space, creating a relaxing setting for guests.

4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!

4.99 out of 5 average rating, 179 reviews

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

5 out of 5 average rating, 144 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

4.94 out of 5 average rating, 166 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

4.9 out of 5 average rating, 217 reviews

Two artificial palm trees with green lights are positioned beside a wooden deck. A blue pool can be seen in the background, alongside dark umbrellas. The space also features a set of long wooden tables and benches, providing ample seating for outdoor gatherings.

Cottage in Innisfil

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

4.99 out of 5 average rating, 174 reviews

The exterior of the guest home is shown, featuring a wooden facade with a slatted accent wall. A well-maintained garden with white peonies and lush green plants surrounds the entrance, which is illuminated by a subtle outdoor light. A door with a simple design is visible.

Farm stay in Essa

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

4.99 out of 5 average rating, 148 reviews

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

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.

4.89 out of 5 average rating, 143 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

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Popular amenities for East Gwillimbury rentals with a pool

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Pool

Free parking on premises

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House rentals with a pool

4.92 out of 5 average rating, 48 reviews

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

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

4.93 out of 5 average rating, 94 reviews

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

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

DianeRating, 5 stars6 days 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.

5 out of 5 average rating, 13 reviews

Home in North York

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars2 weeks ago

My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!

4.85 out of 5 average rating, 75 reviews

Home in North York

Toronto Pool Retreat

JasonRating, 5 stars3 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.

4.89 out of 5 average rating, 19 reviews

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

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 🌎.

4.87 out of 5 average rating, 46 reviews

Home in Mimico-Queensway

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.

Home in Central Etobicoke

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.

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.

4.91 out of 5 average rating, 303 reviews

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

King West Victorian Studio Gem

JessieRating, 5 stars1 month ago

What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.

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Condo rentals with a pool

4.8 out of 5 average rating, 104 reviews

A rooftop pool area is visible, featuring a rectangular pool and a hot tub. Surrounding the pools, a textured stone deck is equipped with three round, concrete stools. The building structure in the background showcases large glass balconies that reflect the sunlight.

Condo in North York

Chic Studio w/ Pool | Near Lawrence West Subway

KayodeRating, 5 stars1 day ago

Andrews Place is perfect for a solo traveler. The property is clean, private, and offers excellent transport access to very interesting places. You can catch a direct bus from Toronto YYZ Airport with no need to change buses, and it's just less than a 10-minute walk to the property from the bus stop. It was truly great value for money.

4.79 out of 5 average rating, 106 reviews

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

Cozy 1-Bedroom Romantic Retreat with full Kitchen

DestinyRating, 5 stars1 day 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!

A bright and airy living area showcases a plush white sectional sofa, paired with a modern light fixture above. Large windows invite natural light, while a sleek kitchen with bar seating is visible in the background. The backyard patio is furnished for outdoor gatherings.

5 out of 5 average rating, 33 reviews

Friday Harbour Ground Floor w/ Large Terrance

AshleyRating, 5 stars6 days ago

We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

4.91 out of 5 average rating, 114 reviews

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

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!

4.93 out of 5 average rating, 152 reviews

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

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.

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.

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!

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.

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