Vacation rentals with a pool in Simcoe County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simcoe County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 294 reviews

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...

Guest favorite

Condo in The Blue Mountains

4.93 out of 5 average rating, 270 reviews

Cozy Studio Mountainside stay in Blue Mountains

Fall colours will arrive soon at Blue. Book your getaway now. This cozy STUDIO ground floor condo is perfect for a couple/small family (Max 4). The unit includes: a comfy queen bed and a pop up sofa bed, bathroom with jacuzzi tub, electric fireplace and full kitchen with everything you need. Free parking. Pool and two shared hot tubs are open daily until October. Tennis courts and access to hiking trails. The Blue Village is only a 5 minute drive away with great local restaurants and shops.

Guest favorite

Chalet in The Blue Mountains

4.97 out of 5 average rating, 236 reviews

The Little Blue Spruce

Welcome to The Little Blue Spruce Chalet, the place to unwind and rejuvenate. Located 5min from the village, this spacious unit comes with everything you might need to make your vacation carefree: fast internet, cable and multiple streaming channels, lots of linens and towels, a washer/dryer and a fully stocked kitchen. Relax on the back patio watching the birds and bunnies, walk 2 min to the pool or take the free shuttle to the village. Message me for more info! LICENCE NO. LCSTR20220000080

Guest favorite

Guest suite in Phelpston

4.96 out of 5 average rating, 202 reviews

Country Escape/Private bright lower/2 Bdrm Suite

A totally separate private basement Apt. Large windows with 9’ ceilings, private entrance through the garage. Perfect for a couple or small family(max4)relaxing getaway. Private patio area, plus full access to backyard. Two comfy bedrooms with queen beds. Spa bathroom with large shower. Large open concept Living area, Game area and KITCHENETTE Roku 75”TV Ex Large Driveway Pool is Heated Jun1-Sept30 Surrounded by Ski Resorts, Beaches, Trails and Vetta Nordic Spa. Check in/out time are firm

Guest favorite

Condo in Innisfil

5 out of 5 average rating, 114 reviews

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!

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 139 reviews

#TheFridayFlat: Winter Wonderland Charming Condo

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!

Guest favorite

Condo in Innisfil

4.87 out of 5 average rating, 183 reviews

Friday Harbour Resort Penthouse Lake Simco

Modern Penthouse with beautiful furniture located in the Friday Harbor Resort with beautiful patio…outside pool in the summer and hot tub year round ..gas barbecues ..seating and dining area with fire place large balcony where smoking is allowed. Beautiful sunset on the right Forest 200acres with beautiful trails Beach area with rental equipment .paddle board .basketball court ..bike rentals… eagle nest golf with the restaurant overlooking golf course Beach club restaurant on the water

Guest favorite

Condo in Oro

4.95 out of 5 average rating, 111 reviews

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. Golfing, , driving range across the road, hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive. Enjoy the onsite amenities- indoor/outdoor pool, hot tub, sauna, gym, , BBQ Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY)

Guest favorite

Farm stay in Essa

4.99 out of 5 average rating, 165 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Guest favorite

Guest suite in Minesing

4.84 out of 5 average rating, 115 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

Condo in Oro

4.89 out of 5 average rating, 149 reviews

4-Bed Country Club Haven with Pool, BBQs, and More

Welcome to our one-of-a-kind 4-bed condo country club, an exceptional destination that caters to large families and offers an unforgettable vacation experience. This uniquely structured property features two separate bedroom suites, with Wi-Fi and a range of outstanding amenities, your every need will be catered to. Dive into the ultimate aquatic experience with our heated indoor/outdoor pool, indulge in the benefits of our sauna, and melt away your cares in the inviting hot tub.

Guest favorite

Cabin in Mono

4.95 out of 5 average rating, 291 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Private yoga and group classes available