
Holiday rentals with a pool in Orillia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Orillia
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

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...

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!

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!

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**

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
Popular amenities for Orillia rentals with a pool
House rentals with a pool

Cute and Cozy House

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

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

Home away from home with a hot tub and pool

Beautiful Cottage w Indoor Pool, Sauna, Pool Table

Luxury Family Home Indoor Pool Hot Tub Lake Access

Luxury Resort Villa on Muskoka Bay Golf Course

Orilluxstay
Apartment rentals with a pool

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

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

Friday Harbour Ground Floor w/ Large Terrance

Nature trail views with cozy patio and firetable!

Luxurious Friday Harbour Condo

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

Friday Harbour Luxury Condo Escape, Sleeps 4

Marina view at Friday Harbour 2bd/2bth Pool option
Other holiday rentals with a pool

Dave & Jenny’s Apartment.

Innisfil Resort - 3 Bed Condo Amazing Views

King Bed Suite | Pool • Hot Tub • Gym Access

Stylish 1 bedroom Pet friendly Condo by Sage Homes

Warm rustic luxury chalet near lake & skiing

NEW Luxurious Corner Unit at Friday Harbour Resort

Spectacular 2 BDRM Penthouse at Friday Harbour

Perfect 2 bedrm resort style unit Getaway-Top Host
Quick stats about holiday rentals with a pool in Orillia
Total rentals
10 properties
Nightly prices starting at
€ 69 before taxes and fees
Total number of reviews
480 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Craigleith Ski Club
- Gull Lake
- Devil's Glen Country Club
- Rocky Crest Golf Club
- Angus Glen Golf Club
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Lakeridge Ski Resort
- Lake Joseph Golf Club
- Mount St. Louis Moonstone
- The Club At Bond Head
- Wooden Sticks Golf Club
- Muskoka Lakes Golf and Country Club
- Bigwin Island Golf Club
- Georgian Bay Islands National Park
- Muskoka Bay Resort
- Windermere Golf & Country Club
- Dagmar Ski Resort
- Barrie Country Club
- The Georgian Bay Club