House holiday rentals in Highlands East

A serene outdoor seating area is situated on a grassy slope, facing a tranquil expanse of Lake Ontario. White chairs are arranged in a circle around a fire pit, with a clear blue sky and distant shoreline enhancing the peaceful ambiance.

4.98 out of 5 average rating, 237 reviews

Fitzroy Lakehouse Waterfront Hot Tub

Fitzroy Lakehouse is a private waterfront bungalow on Lake Ontario with a year-round hot tub and direct water access. Enjoy lake views from the main living area and primary bedroom, plus a 200-foot private rock beach with seasonal stairs from Victoria Day to Thanksgiving. Minutes from Prince Edward County wineries and Consecon, with fast Starlink internet, dedicated workspace, firepit, kids play structure, and EV charger. Ideal for families, couples, and remote workers seeking privacy and views.

FamilyValueCleanliness

4.83 out of 5 average rating, 320 reviews

A stone pathway leads to a fire pit surrounded by colorful Adirondack chairs in red and yellow. The view overlooks the lake, with a dock extending into the water under a clear blue sky, providing a serene setting for gatherings.

Home in Orillia

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

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Home in Algonquin Highlands

4.91 out of 5 average rating, 257 reviews

Stunning Lakefront Retreat: Sauna, Hot Tub, EV Chg

This lakefront home is perfect for your work retreat or family getaway, any time of year. Beautifully decorated and fully furnished, it offers everything you need for a productive yet relaxing stay. Host team sessions with inspiring lake views, recharge in the saltwater hot tub or wood-fired sauna, and unwind on the 400 SF dock. Whether for brainstorming, bonding, or relaxation, this serene retreat blends nature, comfort, and focus seamlessly. Create lasting memories by the lake.

LocationValueRiver

4.97 out of 5 average rating, 155 reviews

Home in Trent Lakes

Luxury 5000sqft+ Waterfront Cottage: Sauna Hot Tub

Welcome to Trillium Landing with no guests chores! No need to take garbage home or complete a million chores. Simply enjoy yourself! Have your family/friends escape to our exquisite retreat only 2 hours away from Toronto. Immerse yourself in serenity at our luxurious 5000 sqft, 6 bedroom, 3 full bathroom property, where modern comfort meets natural beauty. Featuring a sauna/hot tub on the water's edge to take in breathtaking views, this is the definition of relaxation.

ValueLocationCheck-in

4.91 out of 5 average rating, 149 reviews

A spacious living room features large windows offering views of colorful foliage. A cozy fireplace is located on one side, with soft seating arranged comfortably around a central coffee table. Light wood flooring enhances the airy atmosphere.

Home in Bracebridge

River Luxe Muskoka 6BR 5BA w/ Hottub, Wifi 200mb+

Beautiful brand new home boasting 6 bedrooms and 5 bathrooms right in the heart of Bracebridge along the Muskoka river. Enjoy the water on the private dock, fish, go for a paddle, or swim over to the sandy beach across the river. Short walk to Wilson’s falls hiking trail and waterfall. Short bike ride/drive to downtown to explore the shops and local life. Close to Santa’s village, excellent restaurants, cute shops, brewery’s and much more. The home sleeps 12 comfortably.

ValueFamilyCheckout

4.93 out of 5 average rating, 99 reviews

A contemporary cottage exterior is surrounded by lush greenery and decorative stone landscaping. Large glass windows provide ample natural light, while an expansive deck offers access to the outdoors. Potted plants add colorful accents near the stone steps leading up to the entrance.

Home in Haliburton

4 Season Lake Front Cottage

Beautiful cottage on Lake Kashagawigamog. Lakefront executive home on a private, flat property with sandy beach. Huge 1,000 sf deck, 6 hole putting green. Deck by the beach with roof, bar, fridge, outdoor speakers. Long dock with swim ladder. Fire pit area, volleyball/badminton area, horse shoes. Use of non motorized boats. 4 full bedrooms: 3Queens, 2 sets of bunk beds (doubles below and singles above), and a loft. Large kitchen and family room.

FamilyLocationQuiet

4.98 out of 5 average rating, 104 reviews

The exterior of the cottage is presented, featuring a large deck with ample outdoor seating. Below, a fire pit area surrounded by red chairs is visible, along with stone pathways leading through the lush greenery. Large windows reflect the natural surroundings.

Home in Barry's Bay

LUX Lakefront: 6 Bedrooms, 12 Guests, w/Hot Tub

Enjoy our cottage on Halfway (Long) Lake, complete with a private beach and fantastic outdoor amenities. Families can reconnect and create new memories at this 4-season property, boasting spacious 6 bedrooms that can accommodate up to 12 people. Guests can take advantage of complimentary kayaks, a paddleboard, and a pedal boat while swimming off the dock in the pristine lake. Fast Starlink internet (up to 150 mbps) and a dedicated work area.

FamilyLocationView

Home in Monteagle, Ontario.

A spacious bedroom features a large bed with soft bedding and decorative pillows. A colorful floral artwork adorns the wall above the bed, while large windows provide a serene view of the snowy landscape outside.

4.96 out of 5 average rating, 192 reviews

Rose Door Cottage

Quaint and cozy 1 bedroom cottage tucked along the southeastern shore of a small, quiet lake. Recently renovated, the cottage is the perfect romantic getaway. It's located 1 km from snowmobile/ATV trails, 15 minutes from Bancroft and 45 minutes from Algonquin Park. The cottage includes a floating dock with swim ladder, bbq, woodburning outdoor firepit, canoe, kayaks, woodburning indoor fireplace, smart tv with starlink satellite.

ValueFamilyOutdoor spaces

4.97 out of 5 average rating, 347 reviews

An outdoor seating area features several dark wooden Adirondack chairs arranged in a circle around a stone fire pit. Soft glow from string lights adds warmth to the scene, while the modern cottage is visible in the background, nestled among tall trees.

Home in Huntsville

Wolegib Muskoka | Private Nordic Spa + Beach

Welcome to our private, modern Scandinavian-style cottage on 3 acres with conservation land across the water for ultimate privacy and tranquility. Floor-to-ceiling windows fill the space with natural light and showcase stunning views of the Muskoka River. Enjoy your private Nordic spa with a sauna, hot tub, and cold plunge. Just 40 steps from the front door, a private beach and dock offer calm, clear water perfect for swimming.

ValueFamilyAmenities

Home in Prince Edward County

The charming exterior of a converted church is presented, showcasing a striking red brick facade and a steeply pitched roof. Tall trees and lush greenery surround the building, adding to the serene setting. A welcoming entrance with a dark door and steps leads to the front.

4.96 out of 5 average rating, 314 reviews

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

LocationFamilyBathroom

4.97 out of 5 average rating, 149 reviews

A modern cabin is nestled among tall trees, showcasing large floor-to-ceiling windows that invite natural light. A spacious covered porch, framed by lush greenery, features outdoor seating. The grassy area surrounding the cabin adds to the serene atmosphere of the wooded retreat.

Home in Eagle Lake

HyggeHaus—sleek snuggly secluded apres-ski cabin

For a getaway that merges serenity with style; imagination with intention, look no further than HyggeHaus and its private Haliburton Highlands wooded retreat. Indulge in a stay where there is time and space for both leisure and adventure, and where beautiful design enables beautiful experiences. To view a short property video, search Youtube for "HyggeHaus Eagle Lake Haliburton". STR Licence# STR-26-00031

LocationFamilyWalkability

4.95 out of 5 average rating, 140 reviews

The custom-built A Frame cabin is set amidst lush greenery, featuring a striking black exterior and a distinctive peaked roof. A spacious deck extends at the front, furnished with seating, and surrounded by nature for a serene environment.

Home in Bracebridge

Secluded Muskoka A-Frame | Hot Tub, Dock, Firepit

Escape to a private, custom-built A-Frame on 3 acres in the heart of Muskoka—complete with your own dock on a quiet stretch of the Muskoka River. Unwind in the hot tub, paddle the river, or relax by the fire under the stars. ★ Guest favourite with 4.9★ rating ★ One of the few stays in the area with a private hot tub + river access *Please note-all guests must have a minimum of two reviews to book*

ValueLocationHospitality

Popular amenities for Highlands East house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A bright and inviting living area features a yellow accent chair paired with a patterned throw pillow. A round area rug anchors the space, while a wooden side table and a glass-front cabinet add warmth. A large artwork adorns the wall opposite a dining area.

4.95 out of 5 average rating, 110 reviews

Design-Forward Luxury Retreat w/ Pool + Hot Tub

ValueFamilyView

An outdoor pool is framed by lush greenery and a rustic wooden barn. Two lounge chairs with umbrellas provide shaded seating, and a well-maintained grassy area surrounds the pool, creating a peaceful space for relaxation.

4.96 out of 5 average rating, 228 reviews

The Old Stone Farmhouse with Hot Tub & Heated Pool

LocationFamilyLayout

Superhost

An indoor pool is framed by large windows that allow natural light to fill the space. The ceiling features wooden beams that create an airy atmosphere. Two chairs are positioned nearby, and vibrant yellow flowers are visible through an adjacent window.

Home in Orillia

4.77 out of 5 average rating, 105 reviews

Casa ~ Pool ~ Fire Pit ~ BBQ

ValueLocationCheck-in

Superhost

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

4.9 out of 5 average rating, 144 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

ValueLocationQuiet

Superhost

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

4.85 out of 5 average rating, 111 reviews

Ski, Swim, Soak, Boat & Golf

LocationValueBathroom

4.94 out of 5 average rating, 209 reviews

Dragonfield House: a beautiful stay in central PEC

LocationValueBackyard

4.94 out of 5 average rating, 248 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

FamilyValueHospitality

4.86 out of 5 average rating, 103 reviews

The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.

Home in Uxbridge

The Ridge Roost - Uxbridge Township

ValueLocationQuiet

Weekly house rentals

4.84 out of 5 average rating, 153 reviews

A spacious interior features wood-paneled walls and large windows allowing natural light. A wooden dining table with place settings contrasts with the sleek bar area, which includes modern stools. A cozy living space can be seen in the background, enhancing the open concept feel.

Home in Eagle Lake

The Beach House

FamilyValueLong stay

4.94 out of 5 average rating, 47 reviews

A modern cottage is nestled among lush green trees, with a spacious deck extending from the structure. Outdoor seating and a dining area are visible, providing ample space for relaxation and meals. Floor-to-ceiling windows enhance the connection with nature.

Home in Haliburton

Haliburton Cottage on Outlet Bay

FamilyValueHospitality

5.0 out of 5 average rating, 71 reviews

Home in Dysart et al

NEW Aframe w/ sauna, outdoor shower & 2km to town

LocationFamilySleep quality

4.95 out of 5 average rating, 94 reviews

The exterior view showcases a two-level cottage nestled among trees. A spacious wooden deck is emphasized, featuring a large dining table and comfortable seating. A staircase leads from the deck to the yard, where a landscaped area invites relaxation and connection with nature.

Home in Wilberforce

Lakeside getaway with hot tub

FamilyLocationCondition

5.0 out of 5 average rating, 24 reviews

A contemporary two-story house is positioned amongst tall trees, featuring large windows that reflect the soft evening light. In the foreground, a fire pit surrounded by multiple Adirondack chairs provides a cozy outdoor gathering space. The natural landscape adds a serene touch to the setting.

Home in Dysart et al

Luxury Winter Lakehouse | Cube Sauna & Stargazing

FamilyLocationSleep quality

4.91 out of 5 average rating, 22 reviews

Home in Dysart et al

Designer A-Frame | Percy Lake + Cube Sauna

FamilyLocationHospitality

5.0 out of 5 average rating, 55 reviews

A serene view reveals lush green grass leading to a tranquil lake. Adorned with trees and shrubs, the property features a small bunkie and a landscaped garden area, with a rainbow visible in the sky above the distant hills.

Home in Haliburton

Haven’s Willow Waterfront Home *New hot tub&Sauna*

ValueFamilyAmenities

5.0 out of 5 average rating, 7 reviews

Home in North Kawartha

Waterfront cottage on Eels Lake

FamilyLocationComfort

Private house rentals

4.94 out of 5 average rating, 33 reviews

Home in Harcourt

Luxury Waterfront Cottage "The Quiet Place"

ValueLocationComfort

4.96 out of 5 average rating, 53 reviews

The image captures a private lakeside setting during sunrise. Adirondack chairs surround a fire bowl on a circular stone area. A private dock extends into the calm lake, reflecting the soft hues of morning light. Lush greenery frames the scene, enhancing the tranquility.

Home in Kawartha Lakes

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

FamilyLocationHiking

4.94 out of 5 average rating, 35 reviews

Home in Lake of Bays

Echo Lake Retreat, Muskoka, Private Beach and Dock

LocationFamilyBeach

4.93 out of 5 average rating, 40 reviews

Home in Highland Grove

Exclusive Couples Retreat

LocationFamilyAccuracy

4.98 out of 5 average rating, 49 reviews

Home in MacTier

Lakeside Retreat with Waterfront and Sauna

FamilyLocationQuiet

4.96 out of 5 average rating, 50 reviews

The exterior of the property is softly illuminated by string lights, creating a warm ambiance. A spacious patio is visible, featuring seating arrangements made of natural wood. The inviting entrance to the house is framed by lush greenery, enhancing the serene setting.

Home in Tory Hill

Our Happy Place: STR25-00043 (Hottub and Trail)

LocationValueCheck-in

4.94 out of 5 average rating, 35 reviews

An outdoor living space features exposed wooden beams and string lights overhead. Comfortable seating is arranged around a central table, with lush greenery visible through large mesh screens. A scenic view of Horseshoe Lake is seen in the background.

Home in Minden

Willow’s Way

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