Vacation rentals with a pool in Regional Municipality of York

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.

4.97 out of 5 average rating, 376 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.

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.

4.95 out of 5 average rating, 104 reviews

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm

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!

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, 114 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, 178 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.

4.88 out of 5 average rating, 213 reviews

Lake Simco penthouse at Friday Harbour resort

Modern Penthouse with beautiful furniture located in the Friday Harbor Resort with beautiful patio…outside pool in the summer and hot tub year round ..gas barbecues ..seating and dining area with fire place large balcony where smoking is allowed. Beautiful sunset on the right Forest 200acres with beautiful trails Beach area with rental equipment .paddle board .basketball court ..bike rentals… eagle nest golf with the restaurant overlooking golf course Beach club restaurant on the water

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, 214 reviews

A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.

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.

4.95 out of 5 average rating, 102 reviews

Upscale Spa Getaway w/ Private Sauna!

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

Villa in Whitchurch-Stouffville

An aerial view captures a charming property surrounded by vibrant autumn foliage. The landscaped yard features a winding driveway, leading to a welcoming home and a sparkling pool nestled among trees. The colorful leaves enhance the serene atmosphere of the private forest setting.

4.95 out of 5 average rating, 22 reviews

Cedar Escape in 10-Acre Private Forest

Welcome and discover Your Forest Sanctuary. Nestled in a lush 10-acre private forest, find a haven where nature embraces you. Unwind along trails, feel the refreshing forest shower, and gather around the fire pit for magical moments. Indulge in sauna bliss and poolside serenity, immersed in nature's tranquility. Close to the city, yet far from hustle and bustle. Come, relax, and discover the magic of living in harmony with nature. Also enjoy the convenience by hi-speed internet.

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, 142 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!

4.99 out of 5 average rating, 104 reviews

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Apartment in Innisfil

Modern Condo at Friday harbour/Pet Friendly

Welcome to Our Elegant Property We're driven by a genuine passion for creating exceptional guest experiences. Our goal is straightforward: to exceed your unique needs and desires during your stay. More than just providing a place to stay, we want to make your visit memorable and enjoyable. Feel free to reach out if you have any questions. We're here to ensure your stay is comfortable and stress-free. **Additional fees are applied for long term stays**

Vacation rentals for every style

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Luxurious estates for the ultimate escape

Popular amenities for Regional Municipality of York rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 23 reviews

A well-maintained backyard features a circular fire pit surrounded by lush green grass. A fenced area provides privacy, while a tranquil pond is visible in the background, framed by tall reeds. A gazebo offers additional outdoor seating options.

Home in East Gwillimbury

Private river access with pool, canoes, kayak

SrinidhiRating, 5 stars3 weeks ago

Clean space, amenities were good! Responsive host!

4.91 out of 5 average rating, 47 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 stars4 days ago

Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan

4.92 out of 5 average rating, 92 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

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,

5 out of 5 average rating, 13 reviews

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars1 week ago

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

A heated swimming pool surrounded by lush greenery reflects the clear sky above. The pool is framed by a glass fence and features colorful pool toys floating on the surface. A pergola provides shaded seating along the spacious deck, inviting outdoor relaxation.

4.98 out of 5 average rating, 47 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars1 day ago

We had a delightful stay at Jasmine’s place. The space was impeccably clean and thoughtfully decorated, making it feel like a true home away from home. Jasmine was an exceptional host—attentive, communicative, and always ready with helpful replies with my questions. I highly recommend her place to anyone visiting the area and would love to return in the future.

4.73 out of 5 average rating, 26 reviews

The outdoor pool is framed by a stone patio, featuring a serene environment with lush greenery surrounding it. A shaded area with an umbrella and several lounge chairs are positioned nearby, creating an inviting space for relaxation.

Home in Newmarket

"THE BIRD HOUSE" getaway!

MargotRating, 5 stars8 months ago

Megan’s house was just like the pictures. It had lots of beds which was perfect for family traveling to town for a family wedding. The pool table and heated pool were an added bonus.

4.75 out of 5 average rating, 32 reviews

Home in Georgina

Beautiful Waterfront Cottage with Pool&HomeTheater

MeenuRating, 5 stars3 weeks ago

Myself and my friends had a pleasant staycation at Xin’s house in May. I had given a heads up that there will be a 4 months baby with us and they made sure the entire space is clean making it most comfortable especially for the baby. The host was super responsive from the time I booked and replied to my questions in a timely and respectful manner. Highly recommend to anyone looking for a spot not very far from city yet appreciate a peaceful and relaxing atmosphere.

4.86 out of 5 average rating, 74 reviews

Toronto Pool Retreat

JasonRating, 5 stars2 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.

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Condo rentals with a pool

An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.

5 out of 5 average rating, 41 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

ElenaRating, 5 stars9 months ago

We recently had the pleasure of staying at a fantastic condo in Friday Harbour, and we can’t recommend it highly enough! From the moment we arrived, we were greeted with warm hospitality and a stunning view that took our breath away. The condo itself was a perfect blend of luxury and comfort. It was impeccably clean, stylishly decorated, and equipped with all the amenities one could wish for. One of the highlights of our stay was the private balcony, where we spent many mornings sipping coffee and evenings watching the sunset over the harbor. The location of the condo is unbeatable. Just a short walk to charming local shops, restaurants, and the marina, it offered the perfect mix of relaxation and convenience. Overall, our stay at this condo in Friday Harbour was exceptional. It’s clear that the owners have put a lot of thought and care into creating a perfect retreat. If you’re looking for a memorable getaway, this place should be at the top of your list!

4.96 out of 5 average rating, 54 reviews

An outdoor pool area features a curved shape, surrounded by modern high-rise buildings. The pool has a clear blue surface and is enclosed by a glass barrier. Spacious, tiled decking offers room for lounging and relaxation.

Condo in North York,

1 Bedroom Suite

LinoRating, 5 stars1 month ago

Great cozy high rise apartment in a fantastic location. Washer power didn't work and wasn't repaired during the trip. Very nice to have a private parking spot in a garage. Would stay again!

5 out of 5 average rating, 31 reviews

Friday Harbour Ground Floor w/ Large Terrance

WinstonRating, 5 stars3 days ago

Booked this condo for a weekend with some friends! The place was perfect with nice living and sleeping spaces. The yard and patio was a great hang out spot as well. Kitchen was great and the grill was fun to use! The surrounding area is beautiful as well. Overall an excellent place to stay!!

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 Markham

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!

An aerial view captures a vibrant recreational area featuring a large swimming pool surrounded by lounge chairs and umbrellas. The area includes a restaurant with outdoor seating, and a nearby beach area is visible, enhancing the outdoor experience.

4.98 out of 5 average rating, 51 reviews

Romantic Stay at Friday Harbour Resort Lake Simcoe

DianaRating, 5 stars1 week ago

We had an absolutely amazing stay — truly a home away from home! The space was spotless, cozy, and had everything we needed to feel comfortable and relaxed. You can tell a lot of thought and care went into every detail. It was the perfect spot to unwind and recharge.

4.68 out of 5 average rating, 76 reviews

An aerial view highlights the modern building's architecture, featuring spacious balconies and a rooftop pool. The surrounding area displays a mix of urban high-rises and green spaces, with the landscape merging into a waterway in the distance.

Condo in Markham

Luxury Corner View Penthouse Downtown Markham

JoshRating, 5 stars2 weeks ago

excellent stay. wonderful 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 stars3 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!

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.