
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.

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...

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!

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.

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.

Exceptional 2+1 ground floor condo @Friday Harbour
Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!

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.

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!

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

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!

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!

Bohemian Luxury at Friday Harbour Resort Simcoe
Welcome to a Bohemian Paradise in the Heart of Friday Harbour. Treat yourself to a relaxing experience only 1hr from Toronto. This beautifully designed condo was designed to make your experience at Friday Harbour the best it can be. **Convenience** One of the few condos with direct walkout to the courtyard’s Firepit and BBQs. Steps away from Restaurants, Nature Trails, Beach & Boardwalk, Golfing, Live Music Events every Weekend.
Popular amenities for Orillia rentals with a pool
House rentals with a pool

Cute and Cozy House

2 Bd Boardwalk Condo Patio Oasis

Home away from home with a hot tub and pool

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

Countryside walk-out with pool.

Luxury Family Home Indoor Pool Hot Tub Lake Access

Orilluxstay

Ski, Swim, Soak, Boat & Golf
Apartment rentals with a pool

Cozy Stays – Your Fall Getaway at Friday Harbour

Cozy Residence with Walkout to Courtyard

Spacious 1 bedroom condo in Carriage Hills (2248)

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

Resort Condo (1 Bedroom) near Horseshoe & Spa

Friday Harbour Luxury Condo Escape, Sleeps 4

Charming 2 Bed/2 Bath at Friday Harbour Resort

Private 2BR Condo | 4 Beds+Pool+Resort
Other holiday rentals with a pool

FH Penthouse | Luxury 4-Bed | Pool & Hot Tub | BBQ

King Suite-Pool, Hot tub - Near Horseshoe Valley

Innisfil Resort - 3 Bed Condo Amazing Views

Friday Harbour Ground Floor w/ Large Terrance

Clean, bright and cozy walkout basement

Perfect Stay | 2 Bed | Huge Patio | Friday Harbour

Cozy 2BR Garden Walkout to Pier All Seasons Resort

Gym+Pool+PetFriendly+KingBeds
Quick stats about holiday rentals with a pool in Orillia

Total holiday rentals
Explore 10 holiday rentals in Orillia

Nightly prices starting at
Orillia holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 550 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Orillia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Orillia rentals

4.9 Average rating
Orillia stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with pools Simcoe County
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Lakeridge Ski Resort
- Wasaga Beach Area
- Osler Bluff Ski Club
- Pigeon Lake
- Devil's Glen Country Club
- Dagmar Ski Resort
- Gull Lake
- Three Mile Lake
- Georgian Bay Islands National Park
- Bigwin Island Golf Club
- Scandinave Spa Blue Mountain
- Torrance Barrens Dark Sky Conservation Area
- Kee To Bala
- Taboo Muskoka Resort & Golf
- Wye Marsh Wildlife Centre
- Casino Rama Resort
- Bass Lake Provincial Park
- Innisfil Beach Park
- Balsam Lake Provincial Park
- Awenda Provincial Park
- Burl's Creek Event Grounds




