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Vacation rentals with a pool in Oro-Medonte

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Oro-Medonte

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Top guest favorite

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 389 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...

An aerial view captures the layout of Friday Harbour, featuring an expansive marina surrounded by lush greenery and residential buildings. The coastline, with a sandy beach and ample water access, provides recreational opportunities. The serene water reflects the natural beauty of the surrounding landscape.

Condo in Innisfil

4.85 out of 5 average rating, 187 reviews

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

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.

Condo in Innisfil

4.94 out of 5 average rating, 121 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

Escape and unwind in our luxurious, open concept fully furnished 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy the season with access to golf, walking trails, beach, boating, biking, live music, events and weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Laundry

Cottage in Tiny

4.98 out of 5 average rating, 122 reviews

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.

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

Condo in Innisfil

4.93 out of 5 average rating, 180 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Condo in Innisfil

4.95 out of 5 average rating, 121 reviews

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

A spacious studio features a large bed with neutral linens, a seating area with a chair, and a dining table for two. The kitchenette includes modern appliances. The indoor pool area is bright with large windows, showcasing lounge chairs and a serene swimming pool.

4.81 out of 5 average rating, 101 reviews

Spacious King Studio - Pool, Hottub, Kitchenette

Experience luxury and convenience in our spacious studio condo overlooking Horseshoe Valley. Just 20 mins to Barrie or Orillia, our condo offers onsite amenities like indoor/outdoor pool, hot tub, sauna, fitness centre, fire pit, BBQs, and kids play area. Indulge in Vetta Spa nearby, explore the many hiking trails around, ski at Horseshoe Valley or tee off at fantastic golf courses. Explore dining, shopping and nightlife in Craighurst, Barrie, or Orillia. Your perfect getaway awaits!

A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.

Condo in Innisfil

4.88 out of 5 average rating, 155 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

An indoor swimming pool glistens under natural light, with large glass windows framing views of vibrant fall foliage. Comfortable lounge seating is arranged nearby, creating a tranquil relaxation area. The pool features clear, inviting water with lane markers visible in the foreground.

4.88 out of 5 average rating, 258 reviews

Spacious 1-br w jacuzzi 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!

Top guest favorite

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Apartment in Innisfil

4.96 out of 5 average rating, 114 reviews

Modern Condo at Friday harbour/Pet Friendly

Welcome to Our Elegant Property We're driven by a genuine passion for creating exceptional guest experiences. Our goal is straightforward: to exceed your unique needs and desires during your stay. More than just providing a place to stay, we want to make your visit memorable and enjoyable. Feel free to reach out if you have any questions. We're here to ensure your stay is comfortable and stress-free. **Additional fees are applied for long term stays**

A modern recreation center is depicted, featuring large glass windows that provide a clear view of the inviting outdoor pool. Surrounding greenery adds a touch of nature, while picnic tables are positioned on a stone patio, offering outdoor seating options. The bright blue sky enhances the vibrant atmosphere.

4.88 out of 5 average rating, 181 reviews

Private 2BR Condo | 4 Beds+Pool+Resort

Private 4-Bed, 2-Suite Highland Estate retreat - perfect for families and groups. You’ll have the entire suite to yourself with no shared interior spaces. Unlike other Highland Estate listings, this one is fully private. Enjoy two bedrooms, a full kitchen, open-concept living with gas fireplace, two balconies, Wi-Fi, smart TVs, in-suite laundry, and premium resort-style amenities. Pet-friendly, SuperHost-managed, and family-ready.

A modern living area features a comfortable sectional sofa and a sleek coffee table, with a fireplace and TV mounted on the wall. A spacious bedroom showcases a king-sized bed and contemporary decor. A private indoor sauna adds a unique wellness element to the condo.

Home in Innisfil

4.92 out of 5 average rating, 112 reviews

Sauna*King Bed*Fireplace*SmartTV

The perfect spa getaway an hour away from Toronto! Modern and bright fully stocked condo with a 2-3 person indoor sauna, fireplace, and an outdoor fire pit. Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen → Coffee & Espresso bar

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Bungalows

Intimate homes. inviting architecture

Popular amenities for Oro-Medonte rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.

Home in Orillia

4.94 out of 5 average rating, 34 reviews

Cute and Cozy House

A serene landscape is captured, showcasing a calm river surrounded by lush greenery. Various structures, including gazebos and outdoor seating, are visible along the riverbank, while a swimming pool and well-maintained lawn provide inviting spaces for relaxation.

Home in Holland Landing

4.97 out of 5 average rating, 29 reviews

Private river access with pool, canoes, kayak

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

4.87 out of 5 average rating, 62 reviews

2 Bd Boardwalk Condo Patio Oasis

A private swimming pool is surrounded by well-maintained gardens, featuring vibrant green shrubs and flowers. A spacious patio area with outdoor furniture is also visible. The clear blue sky enhances the serene ambiance of this inviting outdoor space.

Home in Midland

4.81 out of 5 average rating, 47 reviews

Our vacation home. Fully equipped. Pool. Fire Pit.

A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.

4.9 out of 5 average rating, 102 reviews

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

A balcony features a round table with two wicker chairs, surrounded by vibrant flowering plants in hanging baskets and pots. In the background, a sparkling blue pool is visible, nestled within a fenced backyard shaded by greenery.

Home in Newmarket

4.86 out of 5 average rating, 28 reviews

Cozy Heated Pool House in Newmarket

The exterior of the villa showcases a modern design with a combination of wood and dark paneling. Large glass doors provide access to a patio area, while a well-maintained lawn offers a green space for outdoor activities.

Home in Gravenhurst

4.96 out of 5 average rating, 45 reviews

Comfort, Luxury and Relaxation

Home in Elmvale

4.88 out of 5 average rating, 81 reviews

Ski, Swim, Soak, Boat & Golf

Condo rentals with a pool

Top guest favorite

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.

Condo in Innisfil

4.97 out of 5 average rating, 86 reviews

Summer Escape at Friday Harbour

Top guest favorite

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.

Condo in Innisfil

4.98 out of 5 average rating, 48 reviews

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

A modern kitchen with sleek cabinetry and a dark countertop is shown, with a double sink and stainless steel appliances visible. The open space leads to a comfortable living area, highlighted by large windows that provide natural light and a view of greenery outside.

Condo in Innisfil

4.89 out of 5 average rating, 46 reviews

Cozy south view suite overlooking the nature trail

Top guest favorite

A rectangular hot tub is set under a wooden pergola, featuring steps leading down into the water. Surrounding greenery and a glass railing provide a sense of openness. Sunlight casts shadows across the stone tiles and water surface.

Condo in Innisfil

4.95 out of 5 average rating, 62 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

The image showcases a spacious outdoor area featuring a swimming pool surrounded by landscaped gardens. Modern buildings with balconies are visible in the background. Seating areas with tables and chairs are arranged around the pool, providing a relaxed atmosphere for guests.

Condo in Innisfil

4.9 out of 5 average rating, 144 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

Top guest favorite

A stylish living area features a soft gray sofa adorned with various decorative pillows in shades of blue. A light wooden coffee table, with a woven basket beneath, is positioned in front. A serene abstract mural in cool tones enhances the calming ambiance.

Condo in Innisfil

5 out of 5 average rating, 47 reviews

Charming 2Bed/2Bath at Friday Harbour Resort

A vibrant yellow towel labeled 'La Dolce Vita' is placed on a textured gray stone surface beside a glistening pool. The sunlight reflects off the water, creating a serene and inviting atmosphere around the pool area.

Condo in Innisfil

4.9 out of 5 average rating, 30 reviews

La Dolce Vita at Friday Harbour | 2 bed|2 bath

Condo in Innisfil

4.89 out of 5 average rating, 219 reviews

Lake Simco penthouse at Friday Harbour resort

Other vacation rentals with a pool

An indoor pool area features a clear blue water surface under a high wooden ceiling. In the upper right corner, a snow-covered ski hill hosts skiers enjoying the slopes. The lower left displays outdoor amenities, showcasing a resort-style pool with surrounding lounge areas. On the lower right, two individuals relax in a hot tub, surrounded by serene spa facilities.

Apartment in Shanty Bay

4.64 out of 5 average rating, 11 reviews

King & Queen Bed, Full Kitchen, Hot Tub, Pool

Top guest favorite

A modern living space is presented, featuring a large kitchen island with bar seating. A comfortable couch, accented with decorative pillows, is positioned near a wall showcasing circular wall art. Natural light floods the area through expansive windows, creating a bright atmosphere.

Vacation home in Innisfil

5 out of 5 average rating, 47 reviews

Innisfil Resort - 3 Bed Condo Amazing Views

Top guest favorite

An inviting outdoor pool is surrounded by green trees and a spacious area for relaxation. The clear blue water reflects the sky, while a patio with lounge chairs is positioned nearby. The house with multiple windows offers views of the pool and the serene surroundings.

Farm stay in Phelpston

5 out of 5 average rating, 20 reviews

El Edén, your dream vacation in Simcoe County

Top guest favorite

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

4.98 out of 5 average rating, 87 reviews

Rustic luxury chalet near beach with private pool

An aerial view showcases a snow-covered property featuring a large heated pool, surrounded by a wooden deck. The building's vibrant red and green accents are visible behind the pool, contrasted against the winter landscape of pine trees and snow.

Apartment in Shanty Bay

5 out of 5 average rating, 4 reviews

King Studio Suite – Sauna, heated Pool

Top guest favorite

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

4.98 out of 5 average rating, 45 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

A modern living area is presented with a light-colored sofa and a cozy blue armchair. A coffee table adorned with flowers centers the space, while built-in shelves display decorative items and a television is mounted on the wall. Soft light filters through the windows, enhancing the serene atmosphere.

Apartment in Innisfil

4.94 out of 5 average rating, 16 reviews

Perfect 2 bedroom Friday Harbor - Getaway-Top Host

A light-filled living area showcases a comfortable sofa and a decorative table with a bowl of limes and lemons. Large sliding glass doors open to a private patio, while soft lighting from a pendant lamp creates a serene ambiance.

Apartment in Innisfil

4.96 out of 5 average rating, 24 reviews

1 Bedroom condo Aquaries Resort

Quick stats about vacation rentals with a pool in Oro-Medonte

Total rentals
410 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
13K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with dedicated workspaces
190 properties have a dedicated workspace

Destinations to explore