
Vacation rentals with a pool in Lake Simcoe
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lake Simcoe
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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...
LocationValueSolo travel

Golf, Spa & Summer Vibes Getaway at Friday Harbour
Welcome to our exquisite 2BR/2BA oasis, where relaxation knows no bounds. Embrace the tranquility of our inviting space. Indulge in the comforts of home with a fully equipped kitchen, cozy living area and two private bedrooms designed for restful nights. Soak in the hot tub's warmth, swim and lounge by the pool or gather round the fire pit for memorable conversations under the stars. Your perfect vacation retreat awaits. Book now to experience luxury, comfort & outdoor delight like never before!
FamilyLocationBathroom

Utopia villa and spa
Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.
FamilyValueHospitality

Pool, Wifi, Free parking, Golf, Laundry, BBQ
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.
LocationValueGetting around

Treehouse on private, isolated forest (300 acres)
You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.
ValueLocationParks

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.
ValueFamilyKitchen

Exceptional 2+1 ground floor condo @Friday Harbour
Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!
FamilyValueCondition

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
ValueFamilyBreakfast

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.
LocationValueCheckout

Ski, Swim, Soak, Boat & Golf
Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.
LocationValueCleanliness

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!
LocationKitchenQuiet

Home away from home with a hot tub and pool
This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.
FamilyLocationAccuracy
Popular amenities for Lake Simcoe rentals with a pool
House rentals with a pool

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
FamilyLocationCleanliness

Toronto Pool Retreat
ValueFamilyComfort

Ravine Paradise ! heated pool and hot tub!
LocationFamilyGetting around

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games
LocationFamilyNearby

The Ridge Roost - Uxbridge Township
ValueFamilySkiing

Serene mountainside home with View/Shuttle Bus
LocationFamilyTV

Rivergrass Oasis | Walk to Village & Pool
LocationFamilyView

King Bed, Pool, Gym, Ravine View, Your Getaway!
FamilyValueBeach
Condo rentals with a pool

Beautifully Furnished New Condo at Friday Harbour
ValueFamilyWifi

Highland Grand Retreat Studio
FamilyValuePool

Friday Harbour Luxury Condo & Pool, Sleeps 4
FamilyValueTV

Lovely 3 Bedroom Condo with Stunning View and Pool
LocationFamilyDecor

Stunning Suite in Horseshoe Valley
FamilyValueGrill

Romantic Country Getaway
ValueLocationBathroom

Hillside Haven: Serene Studio Retreat for 4
ValueFamilyParking

Pet-friendly, 1 BR condo in Horseshoe Valley
FamilyLocationAccuracy
Other vacation rentals with a pool

Cozy Beach Cottage with Pool | Georgian Bay
FamilyValueKitchen

Chalet w/ yard & pool, walk to beach & playground
FamilyValueWalkability

All-Season 2BR Escape at Friday Harbour Resort
ValueFamilyCondition

Cozy beach house on Georgian Bay
FamilyValueDecor

Harbour Views! Enjoy our best rates on 7-day stays
LocationFamilyComfort

5 bdrm home with pool and private lakefront
LocationFamilyWalkability

Charming 2 Bed / 2 Bath at Friday Harbour Resort
LocationFamilyKitchen

Cedar Escape • Sauna • 10-Acre Private Forest
LocationValueLong stay
Destinations to explore
- Montreal Vacation rentals
- Pittsburgh Vacation rentals
- Cleveland Vacation rentals
- Niagara Falls Vacation rentals
- Detroit Vacation rentals
- Mississauga Vacation rentals
- Mont-Tremblant Vacation rentals
- Buffalo Vacation rentals
- Niagara Falls Vacation rentals
- Brampton Vacation rentals
- London Vacation rentals
- Prince Edward Vacation rentals
- Cottage rentals Lake Simcoe
- Hotel rooms Lake Simcoe
- Cabin rentals Lake Simcoe
- Beachfront rentals Lake Simcoe
- Rentals with a sauna Lake Simcoe
- Rentals with lake access Lake Simcoe
- Apartment rentals Lake Simcoe
- Ski-in/ski-out rentals Lake Simcoe
- Rentals with a hot tub Lake Simcoe
- Townhouse rentals Lake Simcoe
- Rentals with a kayak Lake Simcoe
- Rentals with beach access Lake Simcoe
- Condo rentals Lake Simcoe
- House rentals Lake Simcoe
- Bungalow rentals Lake Simcoe
- Waterfront rentals Lake Simcoe
- Luxury rentals Lake Simcoe
- Pet-friendly rentals Lake Simcoe
- Private suite rentals Lake Simcoe
- Family-friendly rentals Lake Simcoe
- Rentals with breakfast Lake Simcoe
- Guesthouse rentals Lake Simcoe
- Lakehouse rentals Lake Simcoe
- Rentals with pools Ontario
- Rentals with pools Canada
- Blue Mountain Village
- Scarborough Town Center
- Toronto Zoo
- Wasaga Beach Area
- Sheppard–Yonge Station
- Torrance Barrens Dark Sky Conservation Area
- York University
- Mount St. Louis Moonstone
- Pigeon Lake
- Fairview Mall
- Vaughan Mills
- Gull Lake
- Awenda Provincial Park
- Lakeridge Ski Resort
- Dagmar Ski Resort
- Scandinave Spa Blue Mountain
- Casino Rama Resort
- Toronto PAN AM Sports Centre
- Georgian Bay Islands National Park
- Sibbald Point Provincial Park
- Three Mile Lake
- Bass Lake Provincial Park
- Wye Marsh Wildlife Centre
- Centennial Beach





