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

A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.

Home in Barrie

4.9 out of 5 average rating, 105 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

Guest favorite

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 390 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

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

Guesthouse in Orangeville

4.95 out of 5 average rating, 369 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.

Top guest favorite

An oval-shaped pool is situated just steps from the sandy beach. Surrounding the pool are several lounge chairs and a shaded gazebo. The calm water of the bay is visible in the background, creating a serene setting for relaxation.

Townhouse in Wasaga Beach

4.97 out of 5 average rating, 133 reviews

Waterfront | Heated Pool, Beachfront, BBQ, AC

Enjoy your morning coffee on your waterfront balcony in your 2 bedroom townhouse, steps away from the beautiful sands of Wasaga Beach. Fall asleep to the rhythmic sounds of the water & watch stunning sunsets from your balcony. Cotton bed linens (680 thread count) & towels included Family friendly with pool & beach- perfect for a summer getaway Located on quiet Beach 4. ~1.5 hr drive from GTA, 20 min to Collingwood/Blue Mountain. 2 parking spots. Perfect for family fun & making new memories!

Guest favorite

Cottage in Tiny

4.98 out of 5 average rating, 123 reviews

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.

Top guest favorite

Apartment in Newmarket

4.99 out of 5 average rating, 188 reviews

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Guest favorite

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

Condo in Innisfil

4.93 out of 5 average rating, 182 reviews

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

Guest favorite

Condo in Innisfil

4.95 out of 5 average rating, 122 reviews

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

Superhost

A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.

Condo in Innisfil

4.87 out of 5 average rating, 158 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!

Superhost

A spacious bed is centered in the room, adorned with a decorative throw pillow. Nightstands are positioned on either side, each featuring a lamp that casts a soft glow. Framed artwork enhances the wall above the bed, contributing to a calming atmosphere.

Condo in Oro

4.75 out of 5 average rating, 288 reviews

Cozy Deluxe Studio 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!

Superhost

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Apartment in Innisfil

4.93 out of 5 average rating, 119 reviews

Modern Condo at Friday harbour/Pet Friendly

Welcome to Our Elegant Property We're driven by a genuine passion for creating exceptional guest experiences. Our goal is straightforward: to exceed your unique needs and desires during your stay. More than just providing a place to stay, we want to make your visit memorable and enjoyable. Feel free to reach out if you have any questions. We're here to ensure your stay is comfortable and stress-free. **Additional fees are applied for long term stays**

Top guest favorite

An indoor swimming pool is surrounded by large windows, allowing natural light to illuminate the clear blue water. A whirlpool section is visible near the poolside, with green trees providing a natural backdrop outside. Safety equipment is available nearby.

Condo in Oro

4.95 out of 5 average rating, 150 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. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY)