Vacation rentals with a pool in Lake Joseph

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake Joseph

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

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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!

Sep 17 – 24

G$22,555 GYD per night

Guest favorite

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.

Sep 18 – 25

G$26,164 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 11 – 18

G$17,357 GYD per night

Guest favorite

Guesthouse in Kawartha Lakes

4.92 out of 5 average rating, 247 reviews

The Loft on Sturgeon Lake

Enjoy the lakeside lifestyle on Sturgeon Lake! This beautiful custom loft features one spacious bedroom with a queen bed and large, bright windows. The suite has a private washroom with a large walk-in shower. There is a full kitchen available and living space with a pull out couch. Experience stunning sunsets over Sturgeon Lake from your private balcony or by the lake at the dockside fire pit. There is an outdoor pool that can be used when available and canoes and kayaks.

Sep 15 – 22

G$28,773 GYD 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

G$26,814 GYD per night

Guest favorite

Condo in The Blue Mountains

4.93 out of 5 average rating, 152 reviews

Le Petite Chalet - Shuttle to Blue / Outdoor Pool

Le Petite Chalet 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.

Oct 23 – 30

G$22,485 GYD per night

Guest favorite

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!

Aug 30 – Sep 6

G$30,602 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 6 – 13

G$20,901 GYD per night

Guest favorite

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 11 – 18

G$25,114 GYD per night

Guest favorite

Chalet in The Blue Mountains

4.94 out of 5 average rating, 291 reviews

Immaculate Blue Mountains chalet

Welcome to our cozy chalet located in walking distance of Blue Mountain village. The chalet has been recently updated, including a luxurious king bed. Through winter, enjoy a relaxing evening by the fire, after a day on the slopes. In summer, enjoy time at the pool, after day on the golf course. The chalet is equipped with everything you need for a tranquil getaway. Enjoy free shuttle service to the village. STA Licence # LCSTR20220000127

May 23 – 30

G$18,859 GYD per night

Guest favorite

Cottage in Wasaga Beach

4.95 out of 5 average rating, 229 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 21 – 28

G$23,324 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

Apr 10 – 17

G$27,098 GYD per night