
Vacation 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!

Utopia villa and spa
Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

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.

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.

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!

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

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!

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

Cute and Cozy House

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

Home away from home with a hot tub and pool

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

Luxury Resort Villa on Muskoka Bay Golf Course

Orilluxstay

Ski, Swim, Soak, Boat & Golf

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

Golf, Spa & Spring Vibes Getaway at Friday Harbour

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

Luxurious Friday Harbour Winter Wellness Escape

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Friday Harbour Luxury Condo Escape, Sleeps 4

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

Bohemian Luxury at Friday Harbour Resort Simcoe
Other vacation rentals with a pool

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

Quiet Country Escape Close To Beach Parks And Golf

Cozy Residence with Walkout to Courtyard

Gym+Pool+PetFriendly+KingBeds

Resort Condo (1 Bedroom) near Horseshoe & Spa

Comfort, Luxury and Relaxation

Cedar Escape • Sauna • 10-Acre Private Forest

NEW Luxurious Corner Unit at Friday Harbour Resort
Quick stats about vacation rentals with a pool in Orillia

Total vacation rentals
Explore 10 vacation rentals in Orillia

Nightly prices starting at
Orillia vacation rentals start at G$14,647 GYD per night before taxes and fees

Verified guest reviews
Over 550 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Orillia vacation rentals include wi-fi 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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- 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
- Georgian Bay Islands National Park
- Three Mile Lake
- Bigwin Island Golf Club
- Scandinave Spa Blue Mountain
- Torrance Barrens Dark Sky Conservation Area
- Taboo Muskoka Resort & Golf
- Kee To Bala
- Burl's Creek Event Grounds
- Casino Rama Resort
- Balsam Lake Provincial Park
- Menominee Lake
- Bass Lake Provincial Park
- Wye Marsh Wildlife Centre
- Innisfil Beach Park




