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

4.98 out of 5 average rating, 214 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...

Nov 30 – Dec 7

G$25,083 GYD per night

Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Dec 5 – 12

G$33,750 GYD per night

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

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!

Oct 11 – 18

G$22,724 GYD per night

Guest favorite

Guest suite in Phelpston

4.96 out of 5 average rating, 185 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 getaway. Max is a family of 4. 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 Extra Large driveway Heated Pool available starting May 10th Surrounded by Ski Resorts, Beaches, Trails and Vetta Nordic Spa.

May 11 – 18

G$27,855 GYD per night

Guest favorite

Cottage in Innisfil

4.94 out of 5 average rating, 151 reviews

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

Sep 16 – 23

G$63,498 GYD per night

Guest favorite

Farm stay in Essa

4.99 out of 5 average rating, 119 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!

Nov 9 – 16

G$35,846 GYD per night

Guest favorite

Condo in Oro

4.88 out of 5 average rating, 118 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.

Nov 13 – 20

G$29,938 GYD per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 106 reviews

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!

Jul 10 – 17

G$17,361 GYD per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 272 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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Feb 25 – Mar 4

G$34,998 GYD per night

Guest favorite

Condo in Oro

4.9 out of 5 average rating, 154 reviews

Spacious 1-br w pool & 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!

Oct 19 – 26

G$20,678 GYD per night

Guest favorite

Cottage in Wasaga Beach

4.95 out of 5 average rating, 230 reviews

GATED RESORT COTTAGE

[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

Oct 29 – Nov 5

G$24,047 GYD per night

Guest favorite

Apartment in Innisfil

4.91 out of 5 average rating, 118 reviews

King Bed*Pool*Fireplace*BBQ*Smart TV

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! 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

Nov 20 – 27

G$24,292 GYD per night