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.

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Guest favorite

Home in Barrie

4.92 out of 5 average rating, 90 reviews

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

Superhost

Vacation home in Port McNicoll

4.9 out of 5 average rating, 10 reviews

Executive vacay, sauna, heated pool, hottub, lake!

In the cusp of the Georgian bay, this large, detached house is custom & newly built, equipped with a heated sports pool (hot tub open all year), 5 bedrooms, Big screen TVs, IPTV, bar, laundry, high speed internet, kitchens, BBQ, fire pit, sauna, Foosball, bikes +more amenities & areas to entertain. Close to epic trails, beaches, lakes, and all of Georgian bay's features-close to stores. Perfect for families or small groups. Mature, respectful crowd, NO PARTIES, Covid cleaning A+, pets ask :)

Superhost

Condo in Wasaga Beach

4.91 out of 5 average rating, 79 reviews

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking

Beachfront! Beachfront! Fabulous Airconditioned Beachfront Townhouse Condo in Wasaga Beach! Firepit/ Fireplace/ Free Wifi/ Free Parking/ 4 Beds in a 2-bedroom cozy townhouse steps from the sandy beaches of Wasaga. Clean and family-friendly complex with pool and beach perfect for summer vacation. Approx 1.5 hours drive from GTA area, and 20 minute drive to Collingwood, 30 Mins to Blue Mountain SKI Hills. ***Outdoor Pool OPEN NOW only available for guest use from Mid of May- September.

Guest favorite

Condo in Oro

4.87 out of 5 average rating, 89 reviews

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!

Superhost

Condo in Innisfil

5 out of 5 average rating, 4 reviews

Luxurious 2-Bed, 2-Bath Furnished - 5 Star Resort

Spectacular view of marine and lake view! Abundant natural light. Opening to a spacious atmosphere. 1,010.00 sf, luxurious living space. 2 bedrooms equipped, 2 upgraded bathrooms. Fully furnished, all brand new furniture. Hot top available all season. Kitchen includes Island, microwave oven, toaster, kettle (all new). Dining table seats four. 65 inch Sony smart TV. Washer & dryer. Over 15 days+ require to pay utilities. Underground parking. Wifi included. long term rental available.

Guest favorite

Home in Oakwood

4.98 out of 5 average rating, 44 reviews

All Season Indoor Pool Escape

This stunning property has completed a full renovation to offer you the ultimate in luxury living. Our estate property features 4 newly renovated large bedrooms, each with an ensuite bathroom. The indoor pool with floor-to-ceiling windows will be the perfect spot for family fun and relaxation, and the basketball pad and outdoor space backing onto a wheat field will provide plenty of opportunities for outdoor activities. Even when it's cold and raining, the indoor pool is a perfect escape!

Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, 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 fall season with access to golf, walking trails, beach, boating, biking, live music & 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

Guest favorite

Guest suite in Minesing

4.85 out of 5 average rating, 130 reviews

Farmhouse GUEST SUITE- Pool, hot tub, horses

Unique Farmhouse stay in modern Guest Suite Wrap around porch for a glass of wine or your morning coffee. Spend a lazy day relaxing in the salt water pool and hot tub. Watch the horses graze in the field and catch the breeze from your spot under the barn beam pergola. Toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in winter months. Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

Guest favorite

Home in Utopia

4.86 out of 5 average rating, 44 reviews

Serene Escape: A Nature Getaway

Escape to our secluded woodland oasis, where privacy and tranquility reign supreme. Our tastefully furnished cottage boasts modern chic décor with all-new furniture, making it the ultimate nature lover's retreat. Discover nearby attractions, including the sands of Wasaga Beach, just 30 minutes away, or hit the slopes at Snow Valley Ski Resort, only 15 minutes drive. Enjoy complete relaxation, surrounded by trees and birds, and take a dip in the pool, available from June to September.

Top guest favorite

Condo in Innisfil

5 out of 5 average rating, 9 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

A sun-drenched patio and corner unit, our space is professionally designed and located in the heart of Friday Harbour close to all attractions. Our place features: → Free secured parking for 1 car → Keyless 24HR self check-in → Over 800 ft² of space → Building features hot tub and pool → 2 stylish and separated bedrooms with comfy mattresses → Close to all Resort features - beach, harbour, golf, restaurants Only an hour north of Toronto, and 20 minutes from Barrie. Come and enjoy!

Guest favorite

Townhouse in Wasaga Beach

4.91 out of 5 average rating, 176 reviews

Scenic WasagaBeach seasonal HeatedPool FireplaceAC

Explore Wasaga Beach right on the shores of Georgian Bay with newly upgraded townhouse, heated seasonal pool, BBQ, outdoor fire pit and grassy play area. Situated right on Beach 4. Relax at the fire pit, stroll the beach, enjoy the fresh air and peaceful scenery. Upper level two bedrooms (sleeps 6). Master BR overlooks beach with gorgeous view of bay and sunset. Main floor kitchen/breakfast area/large TV Winter Activities Blue Mountain Village & Ski Hill Nordic Trail

Guest favorite

Apartment in Innisfil

4.96 out of 5 average rating, 27 reviews

Modern Luxury Delight with a Pool and Hot Tub

Welcome to the Highpoint Condo. This 2 bed / 2 bath third floor suite has a beautiful view of the Pool and Hot Tub. Based in a prime location, this suite is the ideal place to unwind and take in the stunning views of the pool and hot tub. It's the perfect spot to start your day with a cup of coffee or end it with a glass of wine. Look forward to just lounging, sunbathing, or dining al fresco. Come and enjoy this unique and tranquil getaway.