Holiday rentals with a pool in Oro-Medonte

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

5.0 out of 5 average rating, 225 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

LocationFamilyGetting around

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.97 out of 5 average rating, 496 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

ValueLocationCheckout

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.95 out of 5 average rating, 399 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

ValueLocationBackyard

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, 120 reviews

Resort Condo (2 suites) near Horseshoe Valley

Enjoy a stylish experience in this spacious and serene space at Carriage Country Club Resort. A completely equipped designer condo with 2 suites for families looking for perfect vacation. Enjoy a peaceful night in your private Jacuzzi , prepare your own meal in the fully equipped kitchen. Few minutes drive to Horseshoe Valley Resort, and walkable to Vettä Nordic Spa. For Mount St. Louis Moonstone, only about 15 minutes drive away. Our heated indoor/outdoor swiming pool, available year-round.

FamilyLocationCondition

4.96 out of 5 average rating, 170 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

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.

FamilyValueKitchen

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.

4.85 out of 5 average rating, 230 reviews

2BR Horseshoe Condo · Pool · Pet‑Friendly

🌲 Your private base for family adventures in Horseshoe Valley – with pool, hot tub, sauna, and pet‑friendly comfort all in one place. 🌲 This fully private 2‑bedroom Highland Estate condo offers 4 beds total (2 king beds + 2 pullout couches), making it ideal for two families, couples travelling together, or a small group getaway. Enjoy two king‑bed suites, two balconies, in‑suite laundry, and full access to resort‑style amenities just minutes from Horseshoe Resort and Vettä Nordic Spa.

FamilyValueHot tub

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.

4.77 out of 5 average rating, 124 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.

LocationValueQuiet

4.98 out of 5 average rating, 119 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.

FamilyLocationDecor

4.82 out of 5 average rating, 121 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!

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+. Get Some Fun in the Sun and Book Today

ValueFamilyHot tub

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.

4.86 out of 5 average rating, 111 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!

FamilyValueParks

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.

4.98 out of 5 average rating, 125 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.

FamilyValueHospitality

Apartment in Horseshoe Valley

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.

4.83 out of 5 average rating, 121 reviews

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.

ValueFamilyBarbecue

Popular amenities for Oro-Medonte rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 136 reviews

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

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

ValueLocationLaundry

4.95 out of 5 average rating, 22 reviews

Home in Coldwater

Coldwater Cottage Retreat

LocationFamilyBarbecue

4.96 out of 5 average rating, 73 reviews

Home in Coldwater

Modern 6BR Retreat in Horseshoe | Pool + Hot Tub |

FamilyLocationBarbecue

4.77 out of 5 average rating, 99 reviews

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

House ~ Pool ~ Fire Pit ~ BBQ

ValueFamilyCondition

4.94 out of 5 average rating, 78 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

FamilyLocationLong stay

4.78 out of 5 average rating, 27 reviews

Home in Hillsdale

Lost in Hillsdale | Heated POOL | Near Horseshoe

LocationValueAmenities

5.0 out of 5 average rating, 22 reviews

Home in Victoria Harbour

Sunrise

FamilyLocationSleep quality

4.98 out of 5 average rating, 59 reviews

A serene backyard view showcases a well-maintained lawn bordered by diverse greenery and a calm river. Several seating areas, including white chairs and a shaded gazebo, provide relaxation spots. A swimming pool is visible, reflecting the clear blue sky above, creating a peaceful outdoor setting.

Home in East Gwillimbury

Private river access with pool, canoes, kayak

LocationValueAccuracy

Condo rentals with a pool

4.92 out of 5 average rating, 225 reviews

The Friday Flat | Sunny Escape by the Marina

LocationValueParks

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.

4.88 out of 5 average rating, 190 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

FamilyValueBarbecue

A modern living area features a spacious sectional sofa complemented by decorative pillows and a large coffee table. Natural light floods in through expansive glass windows, revealing a view of the private patio. Minimalist decor includes a geometric wall design and a stylish light fixture.

4.92 out of 5 average rating, 136 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

FamilyLocationCondition

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.98 out of 5 average rating, 124 reviews

Golf, Spa & Spring Vibes Getaway at Friday Harbour

LocationValueCheck-in

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.

4.94 out of 5 average rating, 154 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

ValueFamilyCondition

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.

4.85 out of 5 average rating, 188 reviews

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

ValueFamilySleep quality

The living area displays comfortable seating, featuring a dark blue tufted sofa and a black sofa. A wooden coffee table is centered on a light area rug, while a stone fireplace adds warmth. Large windows with light-colored curtains allow for natural light.

4.86 out of 5 average rating, 42 reviews

Elegant 2Suite Condo,Jacuzzi,pool,Horseshoe valley

LocationValueHot tub

4.91 out of 5 average rating, 91 reviews

Highland Grand Retreat Studio

LocationValueHospitality

Other holiday rentals with a pool

4.93 out of 5 average rating, 173 reviews

A modern living space features large windows that provide ample natural light, showcasing a view of the outdoors. A round dining table is surrounded by four chairs, and a cozy seating area includes a sofa and accent pillows. Decorative wall art adds character to the room.

Apartment in Innisfil

All-Season 2BR Escape at Friday Harbour Resort

LocationValueCheckout

4.91 out of 5 average rating, 279 reviews

Cottage in Innisfil

Utopia villa and spa

ValueLocationAccuracy

4.98 out of 5 average rating, 99 reviews

An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.

Guesthouse in Barrie

Chalet w/ yard & pool, walk to beach & playground

FamilyValueBeach

The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.

4.96 out of 5 average rating, 96 reviews

Cozy Residence with Walkout to Courtyard

FamilyValueGetting around

A cozy bedroom is presented with a spacious bed adorned in crisp white linens and a dark throw blanket. Flanking the bed are two bedside lamps, adding soft illumination. A plant adds a touch of greenery, while a living area is visible through an open doorway.

5.0 out of 5 average rating, 19 reviews

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

LocationFamilySkiing

4.98 out of 5 average rating, 46 reviews

A modern kitchen features sleek cabinetry and stainless steel appliances, including an oven and refrigerator. A large island with seating for four is present, complemented by a minimalist design. Soft lighting illuminates the space, enhancing the clean lines and organized layout.

Apartment in Innisfil

Fantastic 1 Bdrm With A View.

LocationWalkabilityHot tub

4.95 out of 5 average rating, 61 reviews

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

Apartment in Innisfil

NEW Luxurious Corner Unit at Friday Harbour Resort

ValueFamilyLayout