Pet-friendly holiday rentals in Keswick

4.86 out of 5 average rating, 286 reviews

A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.

Guest suite in Moonstone

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

4.88 out of 5 average rating, 169 reviews

Cottage in Keswick

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

4.99 out of 5 average rating, 117 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

4.95 out of 5 average rating, 121 reviews

A spacious living area features a high vaulted ceiling and large windows that provide sweeping views of the lake. A stone fireplace and a modern TV complement the cozy seating arrangement, which is paired with a stylish dining area, ensuring a comfortable gathering space.

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

4.77 out of 5 average rating, 381 reviews

The living area features a sectional couch positioned near a small white coffee table, creating a comfortable gathering space. A doorway leads to a staircase, while a kitchenette is visible in the background. Natural light enters through a nearby window, enhancing the neutral decor.

Flat in Innisfil

1 Bedroom Hotel Style Short/Long term Available

Covid19 Clean with Sanitation station set up in main entrance - Come stay at this brand new all-season, private & modern guest suite close to all Innisfil has to offer! 1.2 km away from Lake Simcoe, Big Cedar Golf Course & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

5 out of 5 average rating, 108 reviews

Apartment in Innisfil

Oasis Spa w/ Private Sauna!

Welcome to Our Unique Group of Spa Getaway Suites at Friday Harbour Resort - The Oasis Spa Getaway Rejuvenate, Relax & Unwind with your own private in-suite Sauna and Stunning patio Bamboo Oasis with fire table and Weber BBQ overlooking the pool & hot tub Reconnect with your loved one in our most tropical & romantic suite with multiple fire elements and fully stocked chefs kitchen Professionally designed to take your breath away, a luxury experience to make memories that last a lifetime!

4.98 out of 5 average rating, 253 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

4.97 out of 5 average rating, 111 reviews

A cabin entrance is framed by tall trees, with wooden steps leading up to a doorway. The cabin combines natural elements with modern design, featuring a blend of wood and metal materials. A person approaches the entrance, creating a welcoming scene in a secluded forest setting.

Cabin in Georgina

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Welcome to your next weekend retreat, or work from home during the week in a private nature focused environment with amazing wellness amenities. From the cedar Sauna and hot tub, game corner and indoor gas fireplace- we have your relaxation and entertainment covered. Host your dream dinner party with our gas range stove, pellet smoker and BBQ to choose from. You'll be sounded by cedar forest on all sides on our private road, just 1hr N-E of downtown TO. Ideal for groups of 2-3 couples

4.89 out of 5 average rating, 158 reviews

A rustic cabin, partially visible through snow-covered trees, features a warm wooden exterior. Snow blankets the roof and surrounding ground, while sunlight filters through the branches, creating a serene winter atmosphere. A wrap-around deck is seen at the front of the cabin.

Cabin in Georgina

Romantic Cabin N the Woods just 80km from CN Tower

This Romantic 1 bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Birthdays, Anniversaries, Honeymoons & Proposals! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom! Or simply enjoy a time away to re-connect with your loved one! Sit under stars Year Round in the modern new Hot tub after your run or walk on 200 acres of hilly trails 5kms from the cabin ( Brown Hill Tract)

4.96 out of 5 average rating, 136 reviews

A relaxing outdoor space features a circular fire pit surrounded by four red Adirondack chairs. A stack of firewood sits nearby. Behind the seating area, a glimmering glass geodesic dome is surrounded by lush greenery and open sky.

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 $100/NIGHT ( 2 bunk beds)

Guest suite in New Tecumseth

A spacious living area features a sectional sofa and a wooden coffee table, complemented by a textured area rug. Natural light is provided by recessed lighting, and a white curtain elegantly separates the space. Nearby, a kitchen area with a dining table and modern appliances is visible.

4.85 out of 5 average rating, 325 reviews

Modern, Private and Luxurious!

Welcome to our bright and stylish lower level unit in a friendly new development! You'll enjoy all the comforts of home in this cozy space. Located near Base Borden, the Honda Plant and Baxter Labs. 5 mins from Nottawasaga Inn. 30 mins to skiing at Snow Valley Ski Resort, Hockley Valley Resort, and Mansfield Ski Club. Right around the corner is an awesome community park that features a summer splash pad and a great winter tobogganing hill.

4.84 out of 5 average rating, 244 reviews

Cottage in Innisfil

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

Popular amenities for Keswick pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.9 out of 5 average rating, 459 reviews

A kitchenette area features modern cabinetry and countertop space, illuminated by recessed lighting. Decorative touches, including wall art and greenery, create a welcoming atmosphere. Appliances include a full fridge and microwave, with options for cooking, providing convenience for guests.

Home in Vaughan

Private Lower 1 BR + Sofabed Self Checkin with PKG

4.91 out of 5 average rating, 139 reviews

An open-plan kitchen and dining area is depicted, showcasing modern appliances and cabinetry. A black dining table with four chairs is placed near the entrance, with a small desk nearby. Warm lighting highlights the light-colored flooring and walls, creating a bright and inviting space.

Home in East Woodbridge

Bright Spacious 1BR Basement Suite - Private Entry

5 out of 5 average rating, 10 reviews

A spacious living area features a large sectional sofa, positioned in front of a flat-screen television mounted above a sleek fireplace. Natural light filters through window coverings, creating a bright atmosphere. A geometric area rug adds a touch of color to the tiled flooring.

Home in Sutton

New Home Close to Simcoe

4.86 out of 5 average rating, 154 reviews

An outdoor patio area is designed with comfortable seating arrangements, including a sectional sofa and ottomans. A pergola provides partial shade over the space, while greenery from nearby trees enhances the natural atmosphere. The wooden deck offers ample room for relaxation.

Home in Oak Ridges

Luxurious Spacious Dream Home with Parking!

4.85 out of 5 average rating, 117 reviews

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

Home in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

4.95 out of 5 average rating, 152 reviews

The spacious living area features a light-colored sectional sofa arranged around a circular coffee table. A large Smart TV is mounted on the wall, while abstract artwork adorns the walls. Natural light enters through double doors leading to the patio, complemented by a decorative plant.

Home in Markham

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

5 out of 5 average rating, 20 reviews

Home in Sutton

Cozy Fountain Home

4.88 out of 5 average rating, 214 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

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 63 reviews

An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.

Apartment in Innisfil

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

4.84 out of 5 average rating, 147 reviews

Guest suite in Minesing

Farmhouse Guest Suite; Year round hot tub

5 out of 5 average rating, 59 reviews

A single-story home is seen with a well-manicured lawn and vibrant flower beds. A Canada flag is displayed on the front porch. A driveway accommodates one vehicle, while decorative stones border the driveway, adding a neat touch to the entrance.

Bungalow in Keswick

Dave & Jenny’s Apartment.

4.98 out of 5 average rating, 556 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

4.98 out of 5 average rating, 47 reviews

A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.

Flat in Innisfil

Trendy 1 Bdrm w/Pool & Hot Tub View

4.95 out of 5 average rating, 122 reviews

A modern kitchen area is presented with sleek white cabinetry and black appliances, complemented by a textured backsplash. A dining table with two black chairs sits invitingly, while greenery is introduced by a potted plant in the corner, enhancing the clean and contemporary design.

Home in Scarborough

Cozy Modern Suite•Heated Flrs•Game Rm•Free Pkg

4.87 out of 5 average rating, 199 reviews

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.

Apartment in Oro

Private 2BR Condo | 4 Beds+Pool+Resort

4.91 out of 5 average rating, 56 reviews

The modern kitchen features sleek cabinetry and a spacious island with bar seating. Stainless steel appliances, including an oven and refrigerator, complement the stylish quartz countertops. Natural light filters in from the adjoining living area, creating a bright and open atmosphere.

Apartment in Innisfil

Luxury Living at Friday Harbour High Point

Private, pet-friendly home rentals

4.98 out of 5 average rating, 63 reviews

Two historic barns are nestled among tall grass under a vibrant sky at sunset. The building materials reflect rustic charm, with visible stone and weathered wood, creating a natural contrast against the greenery surrounding them.

Farm stay in Gilford

COOKS BAY farmhouse, 45min from GTA, 2 min 2 lake

4.89 out of 5 average rating, 27 reviews

An open-plan living area features a cozy seating arrangement with a dark sofa and scattered throw pillows. A wooden coffee table is positioned centrally, while a sleek kitchen with modern appliances is visible in the background. Natural light enhances the inviting atmosphere.

Tiny home in Barrie

City Limits Loft

4.86 out of 5 average rating, 64 reviews

An open-concept living area features a spacious sectional sofa and a wooden dining table surrounded by white chairs. Bright lighting illuminates the room, highlighting the modern kitchen with sleek cabinetry and stainless appliances. Large windows allow natural light to enhance the inviting atmosphere.

Cottage in Sutton

Cozy 4 Bdr Cottage Near Lake Simcoe & Beaches

4.94 out of 5 average rating, 36 reviews

A charming cottage exterior is framed by vibrant flowers and lush greenery. The inviting porch features a star decoration above the door, alongside hanging flower baskets. A barbecue grill is positioned to the side, with a clear blue sky and sunlight illuminating the scene.

Home in Willow Beach

Willow Beach Renovated Cottage

4.92 out of 5 average rating, 12 reviews

A spacious backyard is shown, featuring well-maintained grass surrounded by lush greenery. Two black Adirondack chairs sit on a stone patio, inviting relaxation. The sky is partly cloudy, with bright sunlight filtering through the trees.

Flat in East Gwillimbury

Nature-Lovers paradise.

4.69 out of 5 average rating, 48 reviews

A tranquil view of Lake Simcoe at sunset is captured, showcasing shimmering golden reflections on the water. The horizon stretches into the distance, framed by lush greenery and smooth stones along the shoreline.

Cottage in Keswick

Cottage at Lake Simcoe

5 out of 5 average rating, 39 reviews

An open-concept living area features a cozy grey sofa with a textured throw blanket. A stylish rug sits beneath, complementing hardwood flooring. The modern kitchen is visible in the background, equipped with stainless steel appliances and a dining table with chairs near large sliding doors leading to the patio.

Home in Innisfil

Simcoe Retreat