Holiday rentals with a pool in The Archipelago

4.88 out of 5 average rating, 113 reviews

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.

Condo in Huntsville

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.

4.98 out of 5 average rating, 244 reviews

The entrance showcases intricate woodwork and architectural details, with a grand staircase leading to the upper level. A large door opens to the outside, and a vintage chandelier illuminates the inviting foyer, highlighting the craftsmanship of the historic home.

Home in Owen Sound

Butchart Estate: Breathtaking Victorian mansion

Give them a holiday to remember. Gather family or friends and settle in to our beautiful and well-equipped heritage home for a few days. Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, binge some Netflix, or play board games galore. Outdoors, we're famous for our hills, forests, lakes and rivers, the Bruce Trail, and the views out to Georgian Bay. But don't miss the music, museums, the markets, and amazing foodie scene, steps from your door.

4.97 out of 5 average rating, 175 reviews

A sunlit living area is presented with large windows overlooking a snowy landscape. Comfortable seating is arranged around a wooden coffee table. Light walls are complemented by natural wood accents and a colorful rug adds a touch of warmth to the space.

Home in Meaford

Redhill Luxury Home...by the Blue Mountains

This eco friendly house of 4,500 sq ft is bright, modern, luxurious on 50 acres of rolling hills with a beautiful pond and hiking trails. All bedroom ensuite plus 2 extra full bathrooms. Comfortably sleeps up to 24 guests. Amazing view, sunset and star gazing. Salt water pool in the summer. Outdoor BBQ, fire pit, Hot Tub April to Nov. Minutes to Christie beach, ski hills, golf courses, Bruce Trail. Enjoy snowshoeing, cross country. Serenity on top of the hill! See more info under the space.

4.99 out of 5 average rating, 212 reviews

Townhouse in Port Severn

Pool, Wifi, Free parking, Golf, FIFA, Laundry, BBQ

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.

4.96 out of 5 average rating, 151 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.

4.86 out of 5 average rating, 419 reviews

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

4.98 out of 5 average rating, 114 reviews

Cottage in Sprucedale

*HotTub*Private* Pool* trails * Cozy*

Welcome to our enchanting family-friendly log home, a spacious and cozy retreat nestled on a secluded lot, surrounded by a lush canopy of mature trees. If you're seeking peace and tranquility, this is the perfect haven for you. Unique large, cozy log home nestled on a very private lot. Cottage is well furnished and equipped. Indoor and outdoor activities for everyone in your group to enjoy. Enjoy all four seasons at this cottage. The perfect getaway for your family and friends.

4.94 out of 5 average rating, 159 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!

4.94 out of 5 average rating, 139 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

An open living space is displayed, featuring a comfortable sofa adorned with throw pillows. A central coffee table rests atop a patterned area rug, while a wooden dining table with seating for six is visible. The kitchen area is positioned at the back, showcasing modern appliances.

4.87 out of 5 average rating, 103 reviews

Stunning Suite in Horseshoe Valley

Sitting on top of Horseshoe Valley, this stunning and unique condo sets the stage for a memorable and cozy trip. This suite has it all! - Fully stocked kitchen - 6-person dining table - Pull-out couch + loveseat + lounge chair - Cozy fireplace - Comfortable king-size bed - 2-person soaker tub + shower - Private Balcony - Year-round indoor/outdoor pool with hot tub and sauna - Fully equipped gym Minutes away from Vetta Spa, Horseshoe Valley, golf courses and more!

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

4.99 out of 5 average rating, 105 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Welcome to our cozy, modern condo in Horseshoe Valley — the perfect destination for families and groups of friends seeking adventure, relaxation, and unforgettable memories. Just a 2-hour drive from Toronto, our condo offers a prime location to experience it all. Whether you're hitting the slopes, unwinding at the Nordic spa, or exploring the outdoors with mountain biking, golf and tree-top trekking, you'll find everything you need for a perfect getaway.

4.93 out of 5 average rating, 128 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

Private heated pool + year-round hot tub on a secluded 5-acre mountain retreat. Sleeps 10 (max 8 adults) with total privacy. Perfect for ski days and starry-night soaks! Ski Ontario’s best hills by day, then unwind in the year-round hot tub under the stars. Enjoy a private 500ft mountain for sledding, cozy fireplace nights, open-concept living and much more. ✔ Heated Pool (Seasonal) ✔ Hot Tub ✔ Private Sledding Hill ✔ Minutes to Blue Mountain

Popular amenities for The Archipelago rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 60 reviews

The exterior of a renovated house is framed by lush green trees and shrubs. A wooden staircase leads to the front door, enhancing the welcoming entrance. The light blue siding complements the dark green roof, while a driveway is visible alongside the property.

Home in Orillia

Cute and Cozy House

5 out of 5 average rating, 4 reviews

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

The Franklin at Dillon Cove

4.85 out of 5 average rating, 110 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

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

5 out of 5 average rating, 10 reviews

Home in Hillsdale

Lost in Hillsdale | 10 mins to Horseshoe Valley

5 out of 5 average rating, 29 reviews

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

Luxury Resort Villa on Muskoka Bay Golf Course

4.87 out of 5 average rating, 100 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

4.93 out of 5 average rating, 46 reviews

Home in Huntsville

Muskoka Farmhouse w/ Family Amenities | +5 Acres

5 out of 5 average rating, 16 reviews

A hot tub is positioned in the foreground, bubbling gently under a twilight sky. In the background, a modern lakefront cottage with extensive glass windows offers views of the surrounding nature. A well-maintained yard features a pathway leading to the cottage and additional outdoor seating.

Home in Victoria Harbour

Sunrise

Condo rentals with a pool

The exterior of a two-story building features a modern design with white and blue siding. Balconies with white railings are visible, offering shaded spaces and seating options. Lush greenery surrounds the building, contributing to a peaceful atmosphere under a clear blue sky.

4.97 out of 5 average rating, 37 reviews

Resort Escape - Lovely 1 Bedroom + Full Kitchen

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.

4.81 out of 5 average rating, 162 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

A spacious studio features a king-size bed with premium bedding, adjacent to a stylish sectional couch. Natural light pours in through large windows, illuminating the open floor plan. A dining table is positioned nearby, providing a comfortable area for meals.

4.69 out of 5 average rating, 74 reviews

Lux Studio in Horseshoe Valley

A spacious outdoor pool is featured in front of a large red building, showcasing large glass windows. The pool area is surrounded by paved flooring, with a picnic table visible in the background. A lifebuoy is positioned by the pool's edge, emphasizing safety.

4.81 out of 5 average rating, 37 reviews

Resort Condo (1 Bedroom) near Horseshoe & Spa

The bedroom displays a king-sized bed adorned with soft linens and multiple decorative pillows. Next to the bed, a stylish lamp provides warm light, while three framed nature photos hang above the headboard. A cozy seating area features a plush sofa with decorative cushions and a small table, enhancing comfort.

4.98 out of 5 average rating, 48 reviews

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

The living area features a modern design with a large flat-screen TV mounted above a stone fireplace. A cozy gray sofa is paired with a rustic coffee table and a comfortable orange armchair. Natural light enters through double glass doors leading outside.

4.98 out of 5 average rating, 110 reviews

Resort Condo (2 suites) near Horseshoe Valley

The exterior showcases a striking building with a red-and-white color scheme, surrounded by lush greenery. An indoor pool area is visible through large glass windows. An inviting fireplace is framed by stone, while a spacious dining area features a wooden table accompanied by six chairs.

4.86 out of 5 average rating, 213 reviews

Private 2BR Condo | 4 Beds+Pool+Resort

The living area features a comfortable seating arrangement, including a sofa and two armchairs. A coffee table sits centrally on a patterned rug, accompanied by a dining table set for four. A stone fireplace and a mounted TV are also visible, with large windows allowing natural light to enter.

4.9 out of 5 average rating, 90 reviews

Romantic Country Getaway

Other holiday rentals with a pool

Aerial view of a charming multi-unit building surrounded by lush greenery. The structure features a combination of yellow and white exteriors, with distinct architectural details. A paved parking area is visible in the foreground, providing ample space for vehicles.

4.86 out of 5 average rating, 302 reviews

Spacious 1-br w jacuzzi at Horseshoe Valley

4.91 out of 5 average rating, 22 reviews

Luxury Modern Muskoka Retreat

A modern living area features a spacious gray sofa with decorative pillows, an upholstered chair, and a large ottoman placed on a soft area rug. Bright natural light fills the room through expansive sliding glass doors that open to a serene outdoor view.

4.93 out of 5 average rating, 15 reviews

Nordic Elegance Villa in Muskoka

4.87 out of 5 average rating, 98 reviews

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

Chic & Spacious Home|Private Hot tub & Pool

Apartment in Horseshoe Valley

A row of charming units features gabled roofs and inviting porches, framed by colorful trees and well-maintained landscaping. The path leads towards the units, which are complemented by lush lawns and seasonal foliage.

4.83 out of 5 average rating, 72 reviews

Gym+Pool+PetFriendly+KingBeds

An outdoor dining area features a large table surrounded by six chairs, with additional seating provided by two tall chairs nearby. A modern barbecue grill is positioned to the side. The backdrop includes a spacious patio and large windows leading into the villa.

5 out of 5 average rating, 8 reviews

GavenScape a Luxury 3 Bedroom Villa

5 out of 5 average rating, 17 reviews

A modern condominium building is displayed, featuring a mix of white and dark gray exterior walls. Windows are arranged symmetrically, and small trees are placed along the walkway. A pathway leading to the entrance is visible, enhancing the building's contemporary design.

Home in Orillia

Orilluxstay

The exterior of the villa is showcased, featuring a combination of modern and traditional architecture. A stone chimney is positioned on one side, while large windows are framed by wooden panels. The building is set atop a rocky foundation, surrounded by lush greenery.