Vacation rentals with a pool in Georgian Bay

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 384 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...

Guesthouse in Orangeville

4.96 out of 5 average rating, 357 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.

4.95 out of 5 average rating, 105 reviews

Home in Scarborough

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

5 out of 5 average rating, 194 reviews

Townhouse in Port Severn

Top 1% Guest Favourite EV Charger, Golf, Hot Tub

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

4.86 out of 5 average rating, 352 reviews

Tiny home in Meaford

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 heated pool available for the summer months. INTERNET just upgraded! Window Aircon/pool opens end of May or June.

4.97 out of 5 average rating, 111 reviews

Cottage in Tiny

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.

4.94 out of 5 average rating, 167 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

Apartment in The Blue Mountains

4.98 out of 5 average rating, 130 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * New Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convectional oven combo along with a stove top *Shuttle Service *2 Year Round Hot Tubs *Seasonal Pool (open as of May 31st 2025) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

4.99 out of 5 average rating, 174 reviews

Farm stay in Essa

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!

4.95 out of 5 average rating, 105 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!

4.93 out of 5 average rating, 123 reviews

Condo in Huntsville

Your Home Away from Home in Beautiful Huntsville!

Take some time away at this Hidden Valley Hideaway in Huntsville, in Muskoka. Located at the Hidden Valley Resort, next to Deerhurst, this 2-bedroom condominium is perfectly located for all seasons. Winter: Enjoy downhill and cross-country skiing, snowmobile trails, and skating all at your doorstep. Spring/Summer/Fall: Enjoy the beach, water sports, golf, treetop trekking, and so much more. With Arrowhead and Algonquin parks nearby, explore this beautiful part of Ontario!

Chalet in The Blue Mountains

4.84 out of 5 average rating, 785 reviews

Blue Mountain / Collingwood Hill Side Condo

Ski To Ski From - Studio Condo with a mountain view. 5 minute walk to the north chairlift. Easy keypad check in. Relax in style in this beautiful, newly renovated ground floor unit located at the newly remodeled North Creek Resort at Blue Mountain. Located minutes from the award winning le Scandinave Spa, some of the most scenic golf courses in Ontario, the condo is also located in one of the province's prime destinations for lovers of wine, craft beer and cider.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Georgian Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 45 reviews

Home in Midland

Our vacation home. Fully equipped. Pool. Fire Pit.

AnneRating, 5 stars4 months ago

We were so satisfied for being the first time we booked a AIRBNB. We like the clean airy atmosphere when we walked in. Kitchen was fully equipped for our needs. ( I do a lot of cooking ). We were there for 6 weeks. Our hosts were always in contact to make sure our needs were met. We so enjoyed Midland and everyone was so friendly. We highly recommend this AIRBNB👍💗

Home in The Blue Mountains

4.87 out of 5 average rating, 106 reviews

Blue Mountain Retreat w/ Pool + Village Shuttle

AlanaRating, 5 stars1 month ago

We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.

4.93 out of 5 average rating, 220 reviews

Home in Port Perry

Home away from home with a hot tub and pool

CourtneyRating, 5 stars2 weeks ago

lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

Home in The Blue Mountains

4.95 out of 5 average rating, 196 reviews

Pool Open / Serene mountainside home View/Shuttle

TimRating, 5 stars1 month ago

We had a wonderful stay with a family of four including 18 year old teen boys and two dogs. The boys enjoyed the pool table and great tv's while my wife and I enjoyed the great walking and quiet surroundings. It was also easy to have our well trained dogs with us in this location which was wonderful. Thank you Brendan for the terrific stay and allowing us to change our reservation when our plans changed with ease.

4.89 out of 5 average rating, 19 reviews

Home in Elmvale

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago

We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

4.88 out of 5 average rating, 201 reviews

Home in Kimberley

Heart of Kimberley - with views and a hot tub

JoelsonRating, 5 stars2 weeks ago

We had an amazing experience. It’s a beautiful home with modern amenities and a beautiful outdoor area. We arrived in a cozy town with nearby restaurants and general store. It was a very clean and well prepped home. Our host was amazing. She was accommodating and very kind, always responsive and very welcoming. We highly recommend this stay. 10/10 experience.

4.91 out of 5 average rating, 105 reviews

Home in Innisfil

Sauna*King Bed*Fireplace*SmartTV

MuskanRating, 5 stars1 month ago

Tristan’s stay was amazing! From booking to checking out the entire process was seamless, not to mention the amenities in the AIRBNB were amazing - remember to bring your own toiletries but other than that - FANTASTIC stay chef’s kiss! Will definitely check out Tristan’s other listings given his hospitality and professionalism. Thank you again!

4.98 out of 5 average rating, 230 reviews

Home in Owen Sound

The Butchart Estate: your perfect family retreat!

VictoriaRating, 5 stars1 month ago

We enjoyed our stay at Butchart Estate. It was even more lovely in person. The kitchen has everything you could need and more and the pool room was a big hit.

Show all

Condo rentals with a pool

4.98 out of 5 average rating, 159 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

JohnRating, 5 stars3 weeks ago

Our one night stay at Sabine’s was tremendous. The home is well appointed with plenty of space and easy walking distance to the village. Located in a second floor end unit, it’s a place you immediately feel comfortable in. There is a view of the slopes from the main room picture windows and a small deck area with muskoka chairs. There’s a sizeable fridge to store your beverages to drink while soaking up the views. There are two bedrooms on the main floor, and good sized master in the loft with king bed and en suite. Sabine was very communicative and left detailed instructions. Remote check in was a breeze. There is parking available. I would definitely recommend, and would definitely come back.

4.93 out of 5 average rating, 523 reviews

*Blue Mountain Village* Walk To Blue, Pool, HotTub

ChristineRating, 5 stars3 weeks ago

Great location, really close to the village, golf, trails and the Scandinave Spa. Condo unit is exactly as advertised with a comfy sofa to lunge on. Beds are comfortable and all linens and needed amenities were easy to find and use.

4.79 out of 5 average rating, 106 reviews

Condo in Oro

Cozy 1-Bedroom Romantic Retreat with full Kitchen

DestinyRating, 5 stars4 days ago

Loved our stay here!! Can't say enough positive things about our vacation here. Kitchen was fully stocked, clean bathroom and rooms, easy check in and check out and excellent cooling system as it was a hot few days. Amenities were great and welcoming for families, environment was peaceful and we also loved how the balcony backed onto trees and nature. Would 100% stay here again in the future. Thank you!

4.86 out of 5 average rating, 444 reviews

Base of Blue Mountain, Modern Studio

HollyRating, 5 stars1 week ago

Kate was a responsive host and the suite was comfortable. The king sized bed was a dream. The kitchen had everything we needed and there were ice cubes in the freezer upon our arrival.

4.94 out of 5 average rating, 303 reviews

Cozy & Charming Retreat at Blue Mountain

JimRating, 5 stars2 days ago

Clean and well appointed. Looked and felt brand new. Leo and Josie were excellent communicators and very helpful. A great place to stay. Highly recommend.

4.85 out of 5 average rating, 390 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

JustinRating, 5 stars2 weeks ago

Very nice cozy and clean. Easy to find definitely would come back again in the future

4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

VictoriaRating, 5 stars2 weeks ago

Loved this place so much! Shai was amazing. Definitely will be coming back!