Vacation rentals with a pool in Gravenhurst

4.89 out of 5 average rating, 100 reviews

An aerial view captures a spacious cottage surrounded by dense trees. The outdoor area features a private saltwater pool, a hot tub, and a sauna. Decking connects to seating areas, while a trampoline is visible in the yard, emphasizing the tranquil, wooded setting.

Cottage in Haliburton

Lakefront Cottage W Hottub, Pool, Sauna & Kayaks

Tucked in wooded hills w private lake access, our 5-BR, 2.5-bath cottage on Redstone Lake offers perfect getaway. Just 10 mins from outdoor adventures, local shops & LCBO—Haliburton is only 20 mins away. Unwind in private saltwater pool (Jun 5 - Sept), soak in hot tub, detox in sauna, or gather around fire pit under the stars. With fast Wi-Fi, cozy playroom & private lake access for swimming, fishing, kayaking (2), or paddleboarding (1), every moment is yours to enjoy. Questions? Send us a msg

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, 385 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...

Guest suite in Kawartha Lakes

The exterior of a well-maintained home is captured, surrounded by lush greenery and flower beds. A stone pathway leads to the entrance, which features a covered porch with large windows. Colorful flowers add vibrancy to the garden area, complemented by a serene natural setting.

4.98 out of 5 average rating, 390 reviews

A "Peace" of Eden -- Private suite in country home

Quiet country setting surrounded by forest and farmland, bordering on the Altberg Wildlife Sanctuary Nature Reserve. Lower level suite with private entrance includes one separate bedroom, one bed with room divider in the common space, plus a full bath, kitchen facilities, and living area. Once called the "United Nations of birds", we are just a short drive from public beaches, lakes, the Victoria Rail Trail, and Monck's Landing Golf Course (stay and play package available). Fabulous star-gazing!

4.99 out of 5 average rating, 195 reviews

An inviting outdoor seating area is presented, featuring bright orange Adirondack chairs arranged around a stone patio. The backyard is landscaped with green grass and is bordered by wooden fencing, enhancing the sense of privacy. A hot tub is visible in the background.

Townhouse in Port Severn

Top 1% Guest Favourite EV Charger, Golf, Hot Tub

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

4.97 out of 5 average rating, 111 reviews

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.98 out of 5 average rating, 125 reviews

The main living area includes a comfortable sectional sofa and an armchair beside the large windows, offering views of the lake. A wooden dining table with matching chairs is centered beneath a lantern. Natural light fills the space, complemented by warm wooden accents.

Townhouse in Huntsville

Lakehill Haven in Hidden Valley Slope and Lakeside

2 bed, 1.5 bath, 2 levels & spectacular views of Peninsula Lake & mountains. Two balconies to relax on. Enjoy a beach, tennis & basketball courts, sauna, hot tub, indoor & outdoor pool included in price next door at Hidden Valley Resort ( has a bar/restaurant). Ski hill across the road has a variety of hills and when ready, an ice rink on the lake for a game of shinny or fun skate. Also a hill for sledding out front! The area also has numerous places to visit. No water equipment provided.

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, 167 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

4.99 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!

4.95 out of 5 average rating, 106 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!

4.93 out of 5 average rating, 123 reviews

A serene balcony overlooks a sparkling lake, surrounded by lush greenery and distant rolling hills. A single adirondack chair is positioned on the wooden deck, inviting relaxation and enjoyment of the peaceful view.

Condo in Huntsville

Your Home Away from Home in Beautiful Huntsville!

Take some time away at this Hidden Valley Hideaway in Huntsville, in Muskoka. Located at the Hidden Valley Resort, next to Deerhurst, this 2-bedroom condominium is perfectly located for all seasons. Winter: Enjoy downhill and cross-country skiing, snowmobile trails, and skating all at your doorstep. Spring/Summer/Fall: Enjoy the beach, water sports, golf, treetop trekking, and so much more. With Arrowhead and Algonquin parks nearby, explore this beautiful part of Ontario!

4.95 out of 5 average rating, 111 reviews

An indoor heated pool is featured, surrounded by wooden paneling and large windows that provide natural light. A comfortable seating area is positioned nearby, along with exercise equipment visible in the background. The clean water reflects the light, enhancing the serene ambiance.

Cottage in Baysville

Muskoka Forest Chalet with a Private Indoor Pool

Welcome to the beautiful Muskoka Forest Chalet. Equipped with a private indoor pool, wood burning fireplace, home gym, fully stocked kitchen, theatre room, new modern furnishings and much more. Escape the city life with a one-of-a-kind recently upgraded cottage. Whether you are coming with family or friends, our cottage provides a fun and relaxing experience for every guest. Enjoy activities nearby including ice fishing, hiking, snowmobile trails or shopping and dining

4.89 out of 5 average rating, 246 reviews

An indoor swimming pool glistens under natural light, with large glass windows framing views of vibrant fall foliage. Comfortable lounge seating is arranged nearby, creating a tranquil relaxation area. The pool features clear, inviting water with lane markers visible in the foreground.

Condo in Oro

Spacious 1-br w jacuzzi at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Vacation rentals for every style

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Popular amenities for Gravenhurst 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, 28 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

BrianRating, 5 stars1 week ago

Anzhelika’s place was great. The house and property were really well-maintained and exactly as described in the listing. She was a very helpful and accommodating host. The location was great, nice and close to downtown and other amenities. My family and I, including two kids under 10, were very happy with the accommodations. I’d definitely recommend staying here

4.93 out of 5 average rating, 220 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

CourtneyRating, 5 stars2 weeks ago

lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

4.92 out of 5 average rating, 12 reviews

A serene outdoor area features a sparkling swimming pool surrounded by a spacious patio. Comfortable lounge chairs are positioned nearby, while a shaded gazebo provides additional relaxation space. The house in the background showcases a charming design with a distinct gabled roof.

Home in Victoria Harbour

Family & Friends Retreat

SanginiRating, 5 stars8 months ago

Peter is a fantastic host—responsive, flexible, and made everything easy. Highly recommend! We had amazing time with family, it was just perfect stay!! Would visit again in summer when pool is operational :)

Superhost

Home in Elmvale

4.88 out of 5 average rating, 76 reviews

Ski, Swim, Soak, Boat & Golf

JessicaRating, 5 stars3 days ago

Had a great time at the cottage. Everything as pictured, beds were comfy, bathrooms clean, and lots to do including games, kayaking, paddle boarding, plunge pool, and hot tub. The lake isn’t great for swimming but we were never at a loss of things to do because of it. Wasaga is also just a drive away if you want something more lively for a night. Herb was a great host and very responsive, friendly and accommodating :)

4.95 out of 5 average rating, 19 reviews

An expansive green field stretches under a clear blue sky, dotted with fluffy clouds. A round aboveground pool sits to the right, with a ladder for access. Nearby, a designated play area is partially visible, complementing the serene landscape of rolling hills in the background.

Home in Huntsville

Muskoka Farmhouse w/ Family Amenities | +5 Acres

MeenuRating, 5 stars2 weeks ago

Benjamin was very helpful and we requested a late check out and he was very accommodating and let us leave a little later. Great stay and we felt at home!!

4.92 out of 5 average rating, 106 reviews

A modern living area features a comfortable sectional sofa and a sleek coffee table, with a fireplace and TV mounted on the wall. A spacious bedroom showcases a king-sized bed and contemporary decor. A private indoor sauna adds a unique wellness element to the condo.

Home in Innisfil

Sauna*King Bed*Fireplace*SmartTV

RileyRating, 5 stars3 weeks ago

Great host, great location, we enjoyed our stay

4.98 out of 5 average rating, 47 reviews

An aerial view captures the log home nestled among greenery, with a pool surrounded by manicured grass and landscaping. A deck with patio furniture is visible, providing a space for outdoor lounging. The roof features multiple skylights, enhancing the home's natural light.

Home in Fraserville

Kawarthas storybook cottage, hot tub & heated pool

JessicaRating, 5 stars3 weeks ago

We thoroughly enjoyed our stay at “Robins Nest” ❤️ The cabin was even better in person than the pictures showed ! It was quiet and peaceful and definitely felt like a home away from home. Our only regret was not booking it longer! Robin was very thoughtful in leaving welcome treats and a bag of coffee for us upon arrival. She was very responsive and always quick to answer any questions that we had.

Superhost

A spacious patio area features a large table surrounded by several chairs, creating an inviting space for outdoor dining. Potted plants add greenery, while a grill is positioned nearby under a covered structure. A portion of the patio is adorned with stone tiles.

Home in Orillia

4.73 out of 5 average rating, 71 reviews

Luxurious accommodation for 6 Adults

AdamRating, 5 stars3 days ago

The place was perfect. heated pool was a huge bonus. will definitely rent again if in Orillia

Show all

Condo rentals with a pool

A rectangular hot tub is set under a wooden pergola, featuring steps leading down into the water. Surrounding greenery and a glass railing provide a sense of openness. Sunlight casts shadows across the stone tiles and water surface.

4.96 out of 5 average rating, 54 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

StephanieRating, 5 stars1 week ago

My family and I had the best time at Friday Harbour accommodated my Adriana. Her place was beautiful and clean. Literally everything we needed was already thought of and stocked. The condo was walking distance to the main boardwalk area where we found lots to do. My family and I will definitely revisit this condo soon!

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.

5 out of 5 average rating, 10 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

ConradRating, 5 stars3 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.

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.

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!

A modern living space features a cozy sectional sofa and a small coffee table on a patterned area rug. A minimalist dining area is visible with a bowl of fresh fruit and simple seating, while large windows allow natural light to brighten the room.

4.89 out of 5 average rating, 19 reviews

Enjoy your stay at a cozy One bedroom apartment!

YugrajRating, 5 stars3 months ago

"Peaceful and Convenient Stay!" I had a great stay at this Airbnb! The place was very peaceful, making it perfect for relaxation. The location is incredibly convenient—just a 2-minute walk to Starbucks, FH Finefood grocery store, and plenty of restaurants. It made everything super easy, whether I needed coffee, groceries, or a nice meal. The host was also responsive and helpful. I’d definitely recommend this place and would love to stay again.

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

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

VictoriaRating, 5 stars2 weeks ago

Loved this place so much! Shai was amazing. Definitely will be coming back!

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

Joanna LRating, 5 stars12 months ago

Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!