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 favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 216 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...

Dec 12 – 19

ﺩ.ﺇ440 per night

Superhost

Loft in The Blue Mountains

4.79 out of 5 average rating, 197 reviews

Stay A While Chalet - Outdoor Pool / 2 Patios

Stay A While Chalet is 2 bedroom loft 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 tubs year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Jun 17 – 24

ﺩ.ﺇ496 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!

Jun 13 – 20

ﺩ.ﺇ411 per night

Guest favorite

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.

Aug 16 – 23

ﺩ.ﺇ445 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!

Mar 4 – 11

ﺩ.ﺇ650 per night

Guest favorite

Condo in The Blue Mountains

4.89 out of 5 average rating, 200 reviews

1 Bed, 1 Bath Lovely Open Concept Resort Condo

Come and relax by the mountain and enjoy our renovated open concept living space. Our clean & comfortable studio condo has everything you need for a memorable getaway. We want you to have a fantastic time and have stocked our condo with all the things we expect when we travel. You'll find all the extras that make a place special: 40 inch flat screen T.V., fresh linens, well stocked kitchen, newer furnishings & decor, napoleon fireplace, deep jetted tub & free WiFi, NETFLIX and cable.

May 6 – 13

ﺩ.ﺇ251 per night

Superhost

Tiny home in Meaford

4.85 out of 5 average rating, 257 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared pool available for the summer months with possibilities of covid restrictions. INTERNET just upgraded!

Jun 2 – 9

ﺩ.ﺇ361 per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 107 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!

May 10 – 17

ﺩ.ﺇ294 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 Pool available in May. Surrounded by Ski Resorts, Beaches, Trails and Vetta Nordic Spa.

Oct 23 – 30

ﺩ.ﺇ510 per night

Guest favorite

Condo in The Blue Mountains

4.89 out of 5 average rating, 350 reviews

Base of Blue Mountain, Modern Updated Studio

This gorgeous studio chalet is absolutely 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. Blue Mountain Village only 1Km away, as well as the Scandinavia Spa , Northwinds Beach and restaurants. Our chalet is ski in ski out and located right at the North Chair. Come and enjoy all that Blue Mountain has to offer!

Sep 26 – Oct 3

ﺩ.ﺇ473 per night

Guest favorite

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

Sep 23 – 30

ﺩ.ﺇ746 per night

Guest favorite

Condo in Oro

4.9 out of 5 average rating, 157 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 1 – 8

ﺩ.ﺇ362 per night