
Holiday rentals with a pool in Oro-Medonte
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Top-rated rentals with a pool in Oro-Medonte
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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...

Ravine Backyard, King Bed, Jacuzzi, Pool, Hot Tub
Forget your worries in this spacious and serene space at Highland Estates. You get a full designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Prepare your own meals in the fully equipped kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Close to Vetta Spa and major Ski Hills; literally the Best Retreat in Oro-Medonte. Book with Us Today! Please note the Fireplace isn't working.

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.

Private 2BR Condo | 4 Beds+Pool+Resort
🌲Your private headquarters for adventure in Horseshoe Valley! 🌲 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, 4 beds, 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 and SuperHost-managed.

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own 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! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

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

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.

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!

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.

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!

*HotTub*Pool*FirePit*King Bed*
The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a year-round hot tub, outdoor pool, 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 → Year Round Hot Tub → Outdoor Swimming Pool

Cozy getaway for two with hot tub!
Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.
Popular amenities for Oro-Medonte rentals with a pool
House rentals with a pool

Cute and Cozy House

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

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

Beautiful Cottage w Indoor Pool, Sauna, Pool Table

Luxury Resort Villa on Muskoka Bay Golf Course

Luxury Family Home Indoor Pool Hot Tub Lake Access

Ski, Swim, Soak, Boat & Golf

Casa ~ Pool ~ Fire Pit ~ BBQ
Condo rentals with a pool

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

Perfect ~Huge Patio ~ 2BR ~ BBQ ~ Friday Harbour

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Friday Harbour Luxury Condo Escape, Sleeps 4

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

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

Bohemian Luxury at Friday Harbour Resort Simcoe

Resort Condo (2 suites) near Horseshoe Valley
Other holiday rentals with a pool

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

Friday Harbour Ground Floor w/ Large Terrance

Luxurious Friday Harbour Condo

Lux 2BD Apartment in Horseshoe Valley, Oro-Medonte

Warm rustic luxury chalet near lake & skiing

NEW Luxurious Corner Unit at Friday Harbour Resort

Spacious King Studio - Pool, Hottub, Kitchenette

Spectacular 2 BDRM Penthouse at Friday Harbour
Quick stats about holiday rentals with a pool in Oro-Medonte
Total rentals
400 properties
Nightly prices starting at
$31 AUD before taxes and fees
Total number of reviews
14K 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
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- Blue Mountain Village
- Toronto Zoo
- Rouge National Urban Park
- Horseshoe Resort
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Gull Lake
- Devil's Glen Country Club
- Hockley Valley Resort - Golf, Spa and Ski
- Angus Glen Golf Club
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Lakeridge Ski Resort
- TPC Toronto at Osprey Valley
- Lake Joseph Golf Club
- Mount St. Louis Moonstone
- The Club At Bond Head
- Wooden Sticks Golf Club
- Muskoka Lakes Golf and Country Club
- Georgian Bay Islands National Park
- Muskoka Bay Resort
- Windermere Golf & Country Club