Vacation rentals with a pool in East Gwillimbury

4.92 out of 5 average rating, 90 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

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

4.97 out of 5 average rating, 39 reviews

An outdoor patio area is highlighted by a comfortable seating arrangement featuring a soft sofa with accent pillows. A small table sits centrally with decorative items, while green plants add a touch of nature. Large glass doors provide access to the interior space.

Apartment in Innisfil

Trendy 1 Bdrm w/Pool & Hot Tub View

Surround yourself with style in this standout & brand new space. Friday Harbour's Newest Addition. This 1 Bedroom 1 Bath unit with fantastic pool & hot tub views into the beautifully landscaped courtyard. Enjoy strolling the Promenade Boardwalk filled with Restaurants, shops, grocery, LCBO, Starbucks & more. Enjoy the views of the large marina landscaped with boats & jet ski's. The beach is serene and peaceful w/plenty of water activities to enjoy from paddle boards, kayaks, canoes & swimming.

4.86 out of 5 average rating, 87 reviews

A modern swimming pool area is surrounded by sunny greenery and features a large glass wall of the nearby building, giving a bright and open feel. Lounge chairs are positioned nearby, inviting relaxation by the water.

Condo in Oro

Hillside Haven: Serene Studio Retreat for 4

Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

5 out of 5 average rating, 4 reviews

Luxurious 2-Bed, 2-Bath Furnished - 5 Star Resort

Spectacular view of marine and lake view! Abundant natural light. Opening to a spacious atmosphere. 1,010.00 sf, luxurious living space. 2 bedrooms equipped, 2 upgraded bathrooms. Fully furnished, all brand new furniture. Hot top available all season. Kitchen includes Island, microwave oven, toaster, kettle (all new). Dining table seats four. 65 inch Sony smart TV. Washer & dryer. Over 15 days+ require to pay utilities. Underground parking. Wifi included. long term rental available.

4.98 out of 5 average rating, 44 reviews

Home in Oakwood

All Season Indoor Pool Escape

This stunning property has completed a full renovation to offer you the ultimate in luxury living. Our estate property features 4 newly renovated large bedrooms, each with an ensuite bathroom. The indoor pool with floor-to-ceiling windows will be the perfect spot for family fun and relaxation, and the basketball pad and outdoor space backing onto a wheat field will provide plenty of opportunities for outdoor activities. Even when it's cold and raining, the indoor pool is a perfect escape!

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, Sleeps 4

Escape and unwind in our luxurious, open concept fully furnished 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy the fall season with access to golf, walking trails, beach, boating, biking, live music & weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Laundry

4.84 out of 5 average rating, 128 reviews

A modern farmhouse with a spacious wrap-around porch is set against a clear blue sky. In the foreground, a rectangular salt-water pool is surrounded by paved patio and loungers, while green trees frame the serene backyard landscape.

Guest suite in Minesing

Farmhouse GUEST SUITE- Pool, hot tub, horses

Unique Farmhouse stay in modern Guest Suite Wrap around porch for a glass of wine or your morning coffee. Spend a lazy day relaxing in the salt water pool and hot tub. Watch the horses graze in the field and catch the breeze from your spot under the barn beam pergola. Toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in winter months. Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

4.86 out of 5 average rating, 43 reviews

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

Serene Escape: A Nature Getaway

Escape to our secluded woodland oasis, where privacy and tranquility reign supreme. Our tastefully furnished cottage boasts modern chic décor with all-new furniture, making it the ultimate nature lover's retreat. Discover nearby attractions, including the sands of Wasaga Beach, just 30 minutes away, or hit the slopes at Snow Valley Ski Resort, only 15 minutes drive. Enjoy complete relaxation, surrounded by trees and birds, and take a dip in the pool, available from June to September.

5 out of 5 average rating, 9 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

A sun-drenched patio and corner unit, our space is professionally designed and located in the heart of Friday Harbour close to all attractions. Our place features: → Free secured parking for 1 car → Keyless 24HR self check-in → Over 800 ft² of space → Building features hot tub and pool → 2 stylish and separated bedrooms with comfy mattresses → Close to all Resort features - beach, harbour, golf, restaurants Only an hour north of Toronto, and 20 minutes from Barrie. Come and enjoy!

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, 139 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!

4.96 out of 5 average rating, 27 reviews

A hot tub is set within a landscaped area, featuring a shallow section marked at 0.91 meters. Wooden slats create shade overhead, while sunlight creates patterns on the tiled surface. Surrounding greenery and nearby building facades enhance the tranquil environment.

Apartment in Innisfil

Modern Luxury Delight with a Pool and Hot Tub

Welcome to the Highpoint Condo. This 2 bed / 2 bath third floor suite has a beautiful view of the Pool and Hot Tub. Based in a prime location, this suite is the ideal place to unwind and take in the stunning views of the pool and hot tub. It's the perfect spot to start your day with a cup of coffee or end it with a glass of wine. Look forward to just lounging, sunbathing, or dining al fresco. Come and enjoy this unique and tranquil getaway.

4.88 out of 5 average rating, 180 reviews

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. A living area boasts modern furniture, including a sofa and seating around a fire pit. The outdoor pool area is highlighted, alongside the exterior view of the building, showcasing multiple levels.

Home in Innisfil

King Bed*Pool*Fireplace*BBQ*Smart TV

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen

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What guests are saying

Contemporary A Frame on Scugog Island with Pool

4.95 out of 5 average rating, 21 reviews8 months ago

This was our second time staying at the property and it was just as beautiful as the first time. Our family enjoyed the pool and all the amenities offered by the house made us feel very comfortable and right at home. Would recommend for families looking to enjoy some relaxation in peaceful surroundings with all the comforts of home. Thank you for your wonderful hospitality!

Vacation home in Port Perry

What guests are saying

King Bed, Pool, Gym, Ravine View, Your Getaway!

4.89 out of 5 average rating, 63 reviews3 weeks ago

My boyfriend and I had a wonderful stay at Candace and Montu’s townhome. The unit was clean and as described. The hosts were super responsive and proactive with providing instructions for check in and check out. Perfect distance to the Vetta Nordic spa which we enjoyed. 10/10 recommend staying here.

Home in Shanty Bay

What guests are saying

Award Winning Luxury Home with Heated Pool + Sauna

5 out of 5 average rating, 11 reviews3 months ago

This is an excellent Airbnb. We have stayed in many and this was one of the best. The place is very spacious and we could easily fit 6 adults for a weekend of visit with cousins. The furniture is beautiful (it has one of the most comfortable sectionals I have ever had the pleasure of lounging on). The kitchen is extremely well stocked. And most important, Ryan is helpful and responsive. Our young adult son got sick on our trip, and Ryan was happy to let us extend and even sent a link for a local Urgent Care. Just excellent stay all around.

Villa in North York

What guests are saying

El Edén, your dream vacation in Simcoe County

5 out of 5 average rating, 14 reviews7 months ago

Thoroughly enjoyed El Eden for our annual ‘Girls’ weekend. Seven (maturish 😁) ladies all thoroughly enjoyed everything this house has to offer. We loved the privacy and being surrounded by nature. The beds were very comfortable, there’s nice comfortable seating areas inside & out. The pool was a little chilly (being the 3rd week in Sept) but several brave souls made use of it after the hot tub, which was a big hit. Had fun using the tennis court for our introduction to pickle ball. Our group would definitely come back again. Thanks Joanna. We had a super time.

Farm stay in Phelpston

What guests are saying

Large Studio Suite Near Horseshoe

4.87 out of 5 average rating, 54 reviews3 days ago

Great weekend getaway spot for our little family. The pool, playground and pathways for the kids to bike were perfect. We had a dog with us and the grassy space made for easy trips out. The room was clean, check in was easy, and Tim was super responsive. Would definitely book again.

Apartment in Oro

What guests are saying

Bright and Airy Guest Suite with Pool and Sauna

5 out of 5 average rating, 47 reviews6 days ago

We have just stayed for almost 2 weeks here. Shawn was fantastic, always letting us know if there was going to be any work done near the house for the pool (very little and done quickly), quickly responding to us and was generally very helpful. The house is located around a 35-50 minute drive to Toronto, so was helpful to have a car rental. The Air bnb was clean and tidy, there was everything you needed to cook. The bed was the comfiest bed ever and we are now not looking forward to going home to ours because it was so lovely! The bathroom facilities were lovely as well and we generally enjoyed the whole experience! A nice touch was the washer and dryer and I love that I don’t need to do lots of washing when I get home! The place was located near lots of shops and takeaways so was easy to locate food! Really pleased with the whole experience, would definitely return and would definitely recommend to anyone visiting!! Thank you again 😊

Guesthouse in Brampton

What guests are saying

Ski, Swim, Soak, Boat & Golf

4.88 out of 5 average rating, 74 reviews3 weeks ago

Herb was an awesome host. Answered all the questions before hand within a matter of time , place was perfect for our weekend , also helpful to have a handbook of things to do , places to visit , local restaurants ect. Would definitely like to return in the summer for a stay on the water !

Home in Elmvale

What guests are saying

Charming 2BD/2BTH with Hot Tub at Friday Harbour

5 out of 5 average rating, 32 reviews2 months ago

We had an amazing stay at Carissa’s 2-bedroom condo in Friday Harbour. The space was spotless, beautifully maintained, and exactly as described. It had everything we needed for a comfortable and relaxing stay. The location was perfect, allowing us to easily explore all that Friday Harbour has to offer. Carissa was a fantastic host—responsive and accommodating, making the entire experience seamless. We would absolutely stay here again and highly recommend it to anyone looking for a clean, well-equipped, and conveniently located getaway!

Condo in Innisfil

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Popular amenities for East Gwillimbury rentals with a pool

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House rentals with a pool

4.96 out of 5 average rating, 25 reviews

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

Cute and Cozy House

5 out of 5 average rating, 5 reviews

An open-concept living area is flooded with natural light, featuring a modern white sectional sofa on a plush rug. The space includes a kitchen with sleek cabinetry, a dining area visible in the background, and large glass doors that open to the outdoors.

Home in Vaughan

Vacation Getaway with Heated Spa-Pool Open365 Days

Home in Central Etobicoke

An oval heated pool is set in a grassy outdoor area, surrounded by a wooden fence that offers privacy. The sparkling blue water invites relaxation and enjoyment, providing a perfect spot for leisure days.

5 out of 5 average rating, 10 reviews

Luxe Haven Heated Pool Sauna Gym

4.93 out of 5 average rating, 218 reviews

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

Home away from home with a hot tub and pool

4.99 out of 5 average rating, 140 reviews

A private heated pool is framed by stone tiles and lush greenery, reflecting sunlight. Large glass doors lead into the home, enhancing the outdoor connection. Seating areas are available nearby, surrounded by natural landscaping and elevated steps leading to the indoor space.

Home in The Beaches

Heated Pool-tub Open 365 Days

4.88 out of 5 average rating, 41 reviews

Home in Beaverton

Luxury Family Home Indoor Pool Hot Tub Lake Access

5 out of 5 average rating, 3 reviews

A private heated pool is surrounded by a patio featuring red lounge chairs and a small green table. Lush greenery borders the pool area, providing a sense of privacy. A shed is visible in the background, and clear blue skies complete the serene outdoor setting.

Home in East Gwillimbury

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

4.85 out of 5 average rating, 46 reviews

Home in Pickering

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

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Condo rentals with a pool

An aerial view captures a modern courtyard featuring a private outdoor pool, surrounded by sleek buildings. Lounge chairs are positioned along the pool's edge, and landscaped areas with greenery add to the serene atmosphere. Soft light from the evening sky complements the setting.

5 out of 5 average rating, 62 reviews

FH Aquarius Bldg: Modern 2BR/2B Condo

An outdoor balcony features two wicker chairs and a matching table, surrounded by vibrant autumn foliage. The glass railing offers unobstructed views of the colorful trees, while a flat ceiling provides protection from the elements.

5 out of 5 average rating, 11 reviews

Luxurious Friday Harbour Condo

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, 139 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

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, 109 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

5 out of 5 average rating, 4 reviews

Condo in Shanty Bay

Lux 4bd 2bath 1400 sqft Condo

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

Condo in Davisville Village

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.

4.93 out of 5 average rating, 264 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking