Vacation rentals with a pool in Wasaga Beach

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Top-rated rentals with a pool in Wasaga Beach

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

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Guest favourite

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...

Oct. 22 – 29

$184 CAD per night

Guest favourite

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

$156 CAD per night

Guest favourite

Condo in The Blue Mountains

4.92 out of 5 average rating, 246 reviews

Cozy Studio Mountainside stay in Blue Mountains

Summer and Spring are the perfect time to visit Blue. This cozy STUDIO ground floor condo is perfect for a couple or 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. Two shared hot tubs (open daily) and tennis courts. Easy access to for hiking trails. Pool opens in May. The Blue Village is only a 5 minute drive away with great restaurants and shops.

May 2 – 9

$126 CAD per night

Guest favourite

Guest suite in Phelpston

4.96 out of 5 average rating, 184 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

$210 CAD per night

Guest favourite

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

$240 CAD 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. 15 – 22

$147 CAD per night

Superhost

Loft in The Blue Mountains

4.86 out of 5 average rating, 117 reviews

Rustic Loft at Blue

Every season is the best time to enjoy Blue Mountain! Relax with plenty of room for friends or family in our newly renovated lofted studio at beautiful Blue Mountain. Beautiful rustic design, promotes a relaxing stay after skiing the slopes, walking the village, golfing or wandering the trails- all of which are minutes away. Free shuttle service to village and full service restaurant on site. This condo comfortably sleeps 6 people, with 1 King bed, 1 Queen, and 1 sofa bed.

Jun. 3 – 10

$196 CAD per night

Guest favourite

Condo in The Blue Mountains

4.89 out of 5 average rating, 140 reviews

Sweet Retreat - Private Patio / Community Pool

Sweet Retreat is located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tub year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

May 31 – Jun. 7

$169 CAD per night

Guest favourite

Townhouse in Wasaga Beach

4.9 out of 5 average rating, 147 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

Oct. 27 – Nov. 3

$417 CAD per night

Guest favourite

Condo in The Blue Mountains

4.89 out of 5 average rating, 349 reviews

Modern Updated Studio at the Base of Blue Mountain

Our gorgeous studio chalet is perfect for two, or a couple with small children! Newly renovated with a custom kitchen and fireplace. Located right at the base of the ski hill our cozy chalet is a lovely fully furnished 1 bedroom, 1 bath. Our chalet is ski in ski out and located right at the North Chair. Blue Mountain Village only 1Km away, as well as the Scandinavia Spa , Northwinds Beach and restaurants. Come and enjoy all that Blue Mountain has to offer!

Sep. 7 – 14

$229 CAD per night

Guest favourite

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. 6 – 13

$148 CAD per night

Guest favourite

Condo in The Blue Mountains

4.88 out of 5 average rating, 188 reviews

Hidden Haven - Shuttle to Blue / Outdoor Pool

Hidden Haven is located in the peaceful Historic Snowbridge community. Snowbridge is a 2 minute drive, 20 minute walk or a quick shuttle ride to the heart of Blue Mountain Village where you will find the ski hills, restaurants, shops and more. Snowbridge offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, and beautiful walking trails with views of Blue Mountain for guests to use during their stay.

Nov. 13 – 20

$201 CAD per night