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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.

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Top guest favorite

An inviting outdoor seating area is presented, featuring bright orange Adirondack chairs arranged around a stone patio. The backyard is landscaped with green grass and is bordered by wooden fencing, enhancing the sense of privacy. A hot tub is visible in the background.

Townhouse in Port Severn

5 out of 5 average rating, 192 reviews

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

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home We have: -Self check in -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Cable, -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. Sustainable

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 370 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...

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Toronto

4.95 out of 5 average rating, 102 reviews

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm

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!

Cottage in Tiny

4.97 out of 5 average rating, 105 reviews

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.

An outdoor pool area features a modern design with lounge chairs positioned along the water's edge. A wooden pergola provides shaded seating. Surrounding greenery and contemporary building façades enhance the space, creating a relaxing setting for guests.

Condo in Innisfil

4.93 out of 5 average rating, 112 reviews

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!

Top guest favorite

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

Condo in Innisfil

5 out of 5 average rating, 141 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Condo in Innisfil

4.88 out of 5 average rating, 207 reviews

Lake Simco penthouse at Friday Harbour resort

Modern Penthouse with beautiful furniture located in the Friday Harbor Resort with beautiful patio…outside pool in the summer and hot tub year round ..gas barbecues ..seating and dining area with fire place large balcony where smoking is allowed. Beautiful sunset on the right Forest 200acres with beautiful trails Beach area with rental equipment .paddle board .basketball court ..bike rentals… eagle nest golf with the restaurant overlooking golf course Beach club restaurant on the water

Top guest favorite

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

Condo in Innisfil

4.97 out of 5 average rating, 163 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

A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.

Cottage in Innisfil

4.9 out of 5 average rating, 213 reviews

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

Top guest favorite

The exterior of the guest home is shown, featuring a wooden facade with a slatted accent wall. A well-maintained garden with white peonies and lush green plants surrounds the entrance, which is illuminated by a subtle outdoor light. A door with a simple design is visible.

Farm stay in Essa

4.99 out of 5 average rating, 174 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!

An aerial view of the cottage showcases its spacious layout amidst lush greenery along the waterfront. The surrounding trees provide a natural habitat, and features such as multiple patios and a fire pit are visible, creating an inviting outdoor space.

Cabin in Fergus

4.88 out of 5 average rating, 109 reviews

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.

Condo in Innisfil

4.89 out of 5 average rating, 140 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!

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Lake Simcoe rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of a renovated house is framed by lush green trees and shrubs. A wooden staircase leads to the front door, enhancing the welcoming entrance. The light blue siding complements the dark green roof, while a driveway is visible alongside the property.

Home in Orillia

4.96 out of 5 average rating, 26 reviews

Cute and Cozy House

Home in The Blue Mountains

4.89 out of 5 average rating, 221 reviews

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd

A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.

4.92 out of 5 average rating, 91 reviews

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

The exterior of a spacious estate property is showcased, featuring a two-story façade with a mix of brick and siding. The entryway is framed by a covered porch. Lush green lawns and mature trees are visible, enhancing the tranquil outdoor setting.

Home in Oakwood

4.98 out of 5 average rating, 45 reviews

All Season Indoor Pool Escape

Top guest favorite

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in Toronto

4.99 out of 5 average rating, 144 reviews

Heated Pool-tub Open 365 Days

A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.

Home in The Blue Mountains

4.95 out of 5 average rating, 194 reviews

Serene mountainside home View/Shuttle Bus/Pool

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

4.91 out of 5 average rating, 70 reviews

Toronto Pool Retreat

A clear, inviting salt-water pool is seen, surrounded by a paved patio and lush greenery. Comfortable outdoor seating is positioned at one end, offering shaded relaxation beneath a large tree. Bright sunlight reflects off the water, showcasing the pool's tranquil ambiance.

Home in Peterborough

4.91 out of 5 average rating, 66 reviews

New Adventures Edinburgh House/large heated pool

Condo rentals with a pool

Condo in The Blue Mountains

4.98 out of 5 average rating, 154 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

An indoor pool area is visible, featuring a large, rectangular pool surrounded by tiled flooring. Floor-to-ceiling windows allow natural light to fill the space. Lounge chairs are positioned along the edges, and a seating area can be seen in the background.

Condo in Toronto

4.96 out of 5 average rating, 135 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

Top guest favorite

A sleek hot tub is located under a wooden pergola, with the surrounding patio area featuring modern seating arrangements. Bright sunlight streams in, highlighting the contemporary architecture of nearby buildings, while potted plants add a touch of greenery to the space.

Condo in Innisfil

5 out of 5 average rating, 10 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

The image showcases a spacious outdoor area featuring a swimming pool surrounded by landscaped gardens. Modern buildings with balconies are visible in the background. Seating areas with tables and chairs are arranged around the pool, providing a relaxed atmosphere for guests.

Condo in Innisfil

4.91 out of 5 average rating, 142 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

A modern kitchen area features sleek cabinetry and stainless-steel appliances, with an illuminated bar counter offering seating for two. Large windows provide expansive views of the city skyline at dusk, as warm lights from distant buildings create a vibrant evening atmosphere.

Condo in Toronto

4.82 out of 5 average rating, 34 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.

Condo in Blue Mountains

4.92 out of 5 average rating, 341 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.

Condo in Innisfil

4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

A spacious bedroom features a large bed with a light floral-patterned coverlet. Two bedside tables with lamps are positioned on either side, while soft light filters through a window adorned with light curtains. A framed artwork hangs above the bed, contributing to a calming atmosphere.

Condo in Blue Mountains

4.83 out of 5 average rating, 270 reviews

Private Backyard/Shuttle/Pool/10min walk 2 village

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