Family-friendly holiday rentals in Oro-Medonte

4.86 out of 5 average rating, 311 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.

An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.

4.79 out of 5 average rating, 140 reviews

Hillside Haven: Serene Studio Retreat for 4

Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

5 out of 5 average rating, 243 reviews

The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.

Guest house in Barrie

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

4.94 out of 5 average rating, 167 reviews

The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.

Cabin in Innisfil

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

A spacious bedroom is highlighted by a large bed with crisp white linens and a decorative throw pillow. A cozy seating area features a light-colored sofa and lamps, adding to the calm ambiance. Framed artwork and a neutral color palette create an inviting atmosphere.

4.75 out of 5 average rating, 114 reviews

Lovely king size room with kitchenette

An inviting four-season natural playground surrounded by rolling hills and forested trails is located in a spectacular country setting. The Mount St. Louis Moonstone Ski Area is 12 km away, Barrie is 25 km away, and Toronto is 138 km away. Onsite amenities include a pool, fitness center, fire pit, and play area. Nearby, you can enjoy an array of fun attractions and activities for every season! Several convenient perks are available to provide you with the best and most comfortable stay.

4.85 out of 5 average rating, 109 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 Shanty Bay

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

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

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.

4.88 out of 5 average rating, 99 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!

Place to stay in Oro Station

A serene winter landscape is depicted with the sun shining through bare trees. Snow blankets the ground, creating a tranquil atmosphere, while long shadows from the trees stretch across the snow-covered forest floor.

4.96 out of 5 average rating, 111 reviews

The Bunkie- A Cozy Modern Escape

Our cozy, modern Bunkie is nestled in a secluded forest setting with access to local trails and attractions. Whether you are seeking relaxation, adventure or exploration - this beautiful, four season destination will not disappoint. The bunkie has ski in ski out/ ride in ride out access to the Trails at Hardwood Ski and Bike for those who are interested. Trail passes are required, and available at a discount when staying at the bunkie. Contact us for more info.

A spacious bed is centered in the room, adorned with a decorative throw pillow. Nightstands are positioned on either side, each featuring a lamp that casts a soft glow. Framed artwork enhances the wall above the bed, contributing to a calming atmosphere.

4.74 out of 5 average rating, 325 reviews

Cozy Deluxe Studio 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!

5 out of 5 average rating, 204 reviews

A spacious bedroom area features a queen bed adorned with light bedding. A large wall-mounted TV is visible, and a cozy rug lies on the floor. Two comfortable chairs with bright yellow cushions provide seating beside the bed. Natural light streams in through a small window.

Guest suite in Barrie

Private Basement Suite in a family neighborhood

Clean & spacious private Basement suite in a family neighborhood with all amenities that you may require for your stay. Features a queen bed, bathroom and kitchen. Free Parking is included. Highway 400, Park Place, Walmart, Costco, Canadian Tire are within 5-7 minutes driving distance. We offer our guests complete privacy from check-in to check-out, but always available if needed. Perfect for savvy budget travelers who deserve quality stay.

4.83 out of 5 average rating, 109 reviews

The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.

Flat in Shanty Bay

Spacious Hideaway in Nature

Welcome to the charming Shanty Bay area! Embrace the relaxed vibes surrounded by natural beauty. Enjoy leisurely walks by Lake Simcoe or explore nearby parks like Oro-Medonte Rail Trail. Discover local shops and eateries, or indulge in water activities and outdoor adventures. Our cozy Airbnb accommodates 4 guests, with a king-size bed and comfy couches. Experience the best of both worlds - a laid-back getaway and exciting local attractions.

A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.

4.95 out of 5 average rating, 176 reviews

Pet-friendly, 1 BR condo in Horseshoe Valley

All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Popular amenities for Oro-Medonte family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.89 out of 5 average rating, 434 reviews

A cozy cottage is nestled among vibrant autumn foliage. The front features large windows and a welcoming deck, with outdoor seating visible. Surrounding trees display various shades of yellow and orange, contributing to a serene nature setting.

Cabin in Innisfil

Kempenhaus- Lake Simcoe Cottage & Spa | HOT TUB

4.97 out of 5 average rating, 193 reviews

A private outdoor hot tub is surrounded by a lush forest backdrop. The hot tub features jets and clear water, inviting relaxation. The natural scenery includes trees and greenery, enhancing the tranquil setting.

Guest suite in Coldwater

Tranquil Retreat private Hot Tub Horseshoe Valley

4.98 out of 5 average rating, 405 reviews

A hot tub is positioned on a wooden deck, surrounded by natural greenery. Nearby, a fire pit emits a warm glow, creating a cozy atmosphere. Soft outdoor lighting complements the setting, with views of the landscape visible in the background.

Flat in Bracebridge

The Muskoka River Chalet - The King's Den

4.94 out of 5 average rating, 138 reviews

A spacious living area features large windows that invite natural light and offers views of the surrounding greenery. A cozy seating arrangement is positioned around a central coffee table, with a wood stove nearby, complementing the warm wooden ceiling.

Cottage in Bracebridge

Peaceful Muskoka Riverfront Retreat hot tub/Games

4.97 out of 5 average rating, 120 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

4.98 out of 5 average rating, 276 reviews

A cozy sleeping area features a spacious bed adorned with soft linens. A neutral color palette is complemented by light streaming from a nearby window. A modern TV and comfortable seating area are visible in the background, providing a relaxed space for entertainment.

Guest house in Angus

Serene Comfort. Hot Tub, Full Suite with Kitchen

4.99 out of 5 average rating, 102 reviews

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.

Apartment in Innisfil

Bohemian Luxury at Friday Harbour Resort Simcoe

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, 209 reviews

Private 2BR Condo | 4 Beds+Pool+Resort

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 159 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny home in MONO

Whispering Pines Cabin in Woodland Acres

4.9 out of 5 average rating, 251 reviews

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

Deerleap Glamping Dome

Cottage in Victoria Harbour

A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.

4.83 out of 5 average rating, 231 reviews

Serenity, Simplicity and Stone

4.73 out of 5 average rating, 419 reviews

The exterior of the studio apartment is shown, featuring a combination of white and gray siding. A modern garage door and a front door are visible, framed by a small patio area. Trees provide a natural backdrop, with Lake Simcoe glimpsed in the distance.

Cottage in Barrie

The Guesthouse on the North Shore Trail

4.88 out of 5 average rating, 180 reviews

Cottage in Keswick

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

4.98 out of 5 average rating, 203 reviews

An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.

Home in Gravenhurst

Woodland Muskoka Tiny House

4.89 out of 5 average rating, 119 reviews

A modern living space features a comfortable couch positioned in front of a wall-mounted television. A dining area with sleek white chairs is visible, along with a cozy bed beyond a sliding door. Natural light is softly illuminated by recessed lighting.

Flat in Barrie

The Chieftain Suite

4.97 out of 5 average rating, 149 reviews

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 35 reviews

A light-filled living area is furnished with a plush sofa adorned with decorative cushions. A round coffee table sits in the center, accompanied by stylish accent chairs. Natural elements are present, such as a potted plant and woven decorative items, enhancing the serene ambiance.

Flat in Innisfil

Oasis of luxury: 1 bdrm retreat w/Hot Tub Access

4.98 out of 5 average rating, 557 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)

An indoor pool area is highlighted by large windows that allow natural light to fill the space. The pool features a spacious design with inviting seating areas nearby, all surrounded by tasteful wood beams and stone accents, offering a relaxing environment.

4.92 out of 5 average rating, 39 reviews

Spacious 1 bedroom condo in Carriage Hills (2248)

4.88 out of 5 average rating, 177 reviews

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

Apartment in Innisfil

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

4.81 out of 5 average rating, 114 reviews

An outdoor area is presented with a circular seating arrangement made of woven material, positioned around a central table. An umbrella provides shade over the seating. A heated salt-water pool reflects the surrounding greenery, surrounded by a stone patio and wooden fencing.

Flat in Barrie

Beautiful Basement apartment with swimming pool

4.97 out of 5 average rating, 38 reviews

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.

Apartment in Shanty Bay

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

4.85 out of 5 average rating, 188 reviews

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.

Apartment in Innisfil

Marina view at Friday Harbour 2bd/2bth Pool option