Holiday rentals with a pool in Parry Sound District

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Top-rated rentals with a pool in Parry Sound District

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A bright living area features a comfortable gray sectional sofa with yellow accent pillows. A round coffee table sits in front, while large windows allow natural light to fill the space. A ceiling fan hangs overhead, and a piece of wall art adds a touch of color.
Apartment in Huntsville
4.88 out of 5 average rating, 120 reviews

Huntsville Lakeside & Ski Chalet

Enjoy the charm of Muskoka lakeside living at our newly renovated, spacious 3-bedroom, 2-bath chalet on stunning Peninsula Lake. Perfect for families seeking a peaceful getaway—no parties permitted. This lake & ski retreat offers three levels of living space, ensuring everyone has their own private area. The loft BR with private bath provides a peaceful escape with stunning views of the lake and ski hills. Enjoy the sandy beach and outdoor pool in summer, and skiing and snowboarding in winter.

Guest favourite
A wooden sun deck surrounds an above-ground pool, featuring two red lounge chairs positioned for comfort. A potted plant with vibrant flowers adds a pop of colour. Lush green grass and trees are visible in the background, enhancing the outdoor relaxation space.
Cottage in Bracebridge
4.83 out of 5 average rating, 36 reviews

Pool | Sauna | HotTub | Cottage on 8 Acre Forest

Escape to your own private oasis in this charming rural retreat, where tranquility meets convenience. While not waterfront- we've brought the water to you with a sparkling pool, relaxing hot tub, and soothing wood burning sauna—perfect for unwinding after a day of exploration of lakes and waterfalls. Additional sleeping spots are located in the Cozy Cabin - 50ft off main house *NEW* Muskoka Room for a bug-free , rain-free outdoor experience! Santa’s Village - 18 mins Town Centre - 15 Mins

Top guest favourite
A spacious sitting area features a dark sectional sofa and a black armchair, complemented by a rustic wooden coffee table. Large windows provide generous natural light and a view of the lake and surrounding trees. A door leads to the balcony for outdoor relaxation.
Townhouse in Huntsville
4.98 out of 5 average rating, 150 reviews

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.

Guest favourite
A spacious outdoor area features bright blue Adirondack chairs around a stone fire pit. A lawn is visible with lush greenery, and a two-story cottage stands in the background, adorned with string lights. A patio space is equipped with lounge chairs and a large inflatable pool accessory.
Cottage in Severn Bridge
4.95 out of 5 average rating, 22 reviews

Your Getaway to Summer fun in Muskoka

Fun for the whole family. Located on the Trent Seven River just south of Sparrow lake. Swimming off the dock or in the pool your family will truly enjoy this cottage. Campfires in the fire pit by the water making s'mores on warm summers nights. No need to worry about getting to sleep as the cottage is fully air conditioned. Bring your own boat and tie up at the dock there is a private launch 2 mins down the road The cottage is fully stocked with essentials and has high speed internet.

Guest favourite
An aerial view captures the resort’s clubhouse surrounded by vibrant autumn foliage and rolling landscapes. Two outdoor pools are visible, complemented by sun loungers and a rocky terrain. The expansive greenery suggests recreational opportunities nearby, inviting exploration of the diverse natural surroundings.
Villa in Gravenhurst
4.89 out of 5 average rating, 27 reviews

ScandinaVilla Retreat

ScandinaVilla, an Exquisite Scandinavian-Style Private Villa is surrounded by a lush forest landscape and nestled on the grounds of the sought after Muskoka Bay Golf Resort community. Enjoy golfing, hiking trails, cycling, and water activities in nearby nature & beaches in the summer; and snowshoeing, cross country skiing, ice fishing and ice skating in the winter months. Visit the clubhouse and benefit from all its amenities including state of the art gym & 5-star dining experience!

Top guest favourite
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.
Apartment in Huntsville
4.94 out of 5 average rating, 161 reviews

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!

Guest favourite
A dining area features a round table set with a light tablecloth, surrounded by black and green chairs. A lantern and small plant are placed on a tray. Large windows provide a view of the lake at sunset, enhancing the natural light.
Cottage in Callander
4.83 out of 5 average rating, 30 reviews

Private Lake front 3 bedroom cottage #6

Private Lakefront 3 Bedroom Cottage on the sheltered South Bay of Lake Nipissing. Enjoy the sunsets on your lakeside deck. Fantastic lake views. Wonderful vacation destination. Tom Rae Lodge has six lakefront well-appointed cottages. Canoes, kayaks, and paddle boats are included. Fishing boat rentals and dockage available. Seasonal Inground heated pool, whirlpool, children's activity center, and outdoor games for all to enjoy. All cottages have their own BBQs and campfire area.

Guest favourite
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
4.94 out of 5 average rating, 142 reviews

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

Superhost
A living area features two comfortable sofas arranged around a wooden coffee table, which holds decorative items. A dining table with white chairs is positioned nearby, and the wall displays a subtle blue texture, adding visual interest to the space.
Home in Carling
5 out of 5 average rating, 4 reviews

The Franklin at Dillon Cove

- 3-bedroom rental overlooking the bay– perfect for families or small groups - Sleeps up to 6+ guests with 1 queen bed, 1 double bed, bunk bed, and a futon - Step outside to your private deck with comfortable patio furniture for relaxing outdoors - Equipped with a coffee maker and microwave for convenient meals - Dishes and utensils included for all your cooking needs - Fire TV available for your entertainment - 4-piece bathroom (tub, shower, toilet, sink) - Propane BBQ

Top guest favourite
An aerial view of a spacious cottage surrounded by greenery, featuring a gravel area with six red Muskoka chairs arranged around a central firepit. The sunset casts a warm glow over the landscape, enhancing the natural beauty of the property.
Bungalow in Bracebridge
4.87 out of 5 average rating, 99 reviews

Chic & Spacious Home|Private Hot tub & Pool

This is the perfect place for a relaxing getaway! The spacious 2500sqft cottage is situated on a stunning 2.5 acre property with plenty of privacy, peace and quiet. This luxurious 4 bedroom , 3 bathroom cottage is a 3 minute drive to the Muskoka Highlands Golf course and is 4 minutes away from downtown Bracebridge. It features an outdoor hot tub, pool, firepit and much more.

Top guest favourite
A modern living room is presented, featuring a deep grey sofa and a round coffee table at its center. Two abstract artworks adorn the walls, while large sliding glass doors provide views of a snowy landscape outside. A cozy armchair and decorative plants add warmth to the space.
Home in Gravenhurst
5 out of 5 average rating, 29 reviews

Luxury Resort Villa on Muskoka Bay Golf Course

Brand new, luxury Villa on award winning golf course in Muskoka Bay Resort. Whether you're staying with friends to fine tune your golf game, relaxing at the clubhouse pool and sauna, or bringing the family for some quality time together, our Villa will provide you with the warmth and comfort you deserve. Note: Seasonal 2026 opening date for the outdoor heated pool is TBD.

Top guest favourite
The exterior of the rustic cottage showcases a blend of wood siding and large windows, surrounded by lush greenery and colorful flower beds. A spacious gravel driveway leads to the entrance, which features a red door and modern garage. Natural light highlights the inviting façade.
Cottage in Huntsville
4.95 out of 5 average rating, 171 reviews

Luxury Cottage /Chalet, Muskoka Canada

Experience the Canadian Muskoka wilderness in style with year round amenities. Our private cottage/ski chalet is located in a resort-style neighbourhood with shared beach water access and Hidden Valley Ski Hill, in Hidden Valley, Huntsville, Ontario, 2.5hours north of Toronto For weekly rentals in July August we prefer a Friday to Friday if possible.

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