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Vacation rentals with a pool in Simcoe County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simcoe County

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

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Top guest favorite

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, 395 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...

Top guest favorite

Condo in The Blue Mountains

4.95 out of 5 average rating, 902 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB, SEASONAL POOL 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ Enhanced Cleaning Protocol ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms Pool closing for the season on September 22. Hot Tub open all year round!

Top guest favorite

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

Guesthouse in Orangeville

4.95 out of 5 average rating, 372 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.

Cottage in Tiny

4.97 out of 5 average rating, 129 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 shared swimming pool is framed by a green lattice structure and surrounded by lush foliage. The area is paved with light concrete, providing a space for lounging. A shallow edge of the pool is visible, with trees offering shade in the background.

Townhouse in The Blue Mountains

4.96 out of 5 average rating, 216 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Welcome to Apres Blue at Blue Mountain! Unbeatable location @ 110 Fairway Court, only a 5 minute walk to Blue Mountain Village, Ski lifts & Monterra Golf Course. Professionally decorated ground floor unit with full kitchen, gas fireplace, high speed internet, walk out private patio with outdoor dining area, private gas BBQ and shared seasonal pool. This spacious ground floor, 2 bedroom, 2 full bathroom end unit townhouse has everything you need to enjoy your stay! License #LCSTR20230000084

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, 166 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!

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

4.93 out of 5 average rating, 185 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 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

4.87 out of 5 average rating, 164 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!

A modern living area features a large wall-mounted TV and a stylish black accent wall. Two small coffee tables in front of a comfortable sofa are complemented by decorative items. Natural light streams in through the sliding glass doors, which lead to the balcony.

Apartment in Innisfil

4.93 out of 5 average rating, 120 reviews

Modern Condo at Friday harbour/Pet Friendly

Welcome to Our Elegant Property We're driven by a genuine passion for creating exceptional guest experiences. Our goal is straightforward: to exceed your unique needs and desires during your stay. More than just providing a place to stay, we want to make your visit memorable and enjoyable. Feel free to reach out if you have any questions. We're here to ensure your stay is comfortable and stress-free. **Additional fees are applied for long term stays**

A modern living area features a light-colored sofa with decorative pillows, accompanied by a clear glass coffee table. A sleek chair is positioned beside the comfortable seating. Large glass doors provide views of the outdoor area, with sleek kitchen cabinetry visible through the open layout.

Condo in Innisfil

4.82 out of 5 average rating, 507 reviews

Lovely 2-bedroom at Friday Harbour

Friday Harbour Resort welcomes you to the start of something extraordinary. Friday Harbour was designed to be a destination. A destination you look forward to visiting all year round, where you can unwind and truly feel relaxed. Whether you arrive to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of way to enjoy your days.

A modern living area features a comfortable sectional sofa and a sleek coffee table, with a fireplace and TV mounted on the wall. A spacious bedroom showcases a king-sized bed and contemporary decor. A private indoor sauna adds a unique wellness element to the condo.

Home in Innisfil

4.92 out of 5 average rating, 114 reviews

Sauna*King Bed*Fireplace*SmartTV

The perfect spa getaway an hour away from Toronto! Modern and bright fully stocked condo with a 2-3 person indoor sauna, fireplace, and an outdoor fire pit. 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 → Coffee & Espresso bar

Top guest favorite

A spacious living area features a modern kitchen with stainless steel appliances and light cabinetry. A comfortable sofa is paired with a low coffee table, adorned with greenery. Natural light flows in through large windows, enhancing the inviting space.

Apartment in Coldwater

4.96 out of 5 average rating, 104 reviews

Cozy getaway for two with hot tub!

Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

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Convenient locations with everyday essentials

Popular amenities for Simcoe County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.

Home in Orillia

4.95 out of 5 average rating, 41 reviews

Cute and Cozy House

A community heated outdoor swimming pool is surrounded by lush greenery and a variety of seating options, including blue umbrellas. The clear blue water reflects the sky, creating a serene setting for relaxation. Lounge chairs are positioned along the poolside for guest use.

Home in The Blue Mountains

4.89 out of 5 average rating, 240 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

4.88 out of 5 average rating, 66 reviews

2 Bd Boardwalk Condo Patio Oasis

An open-concept living area is displayed, featuring a gas fireplace with a mounted television above it. A spacious wooden coffee table is centered on a light-colored rug. The dining area, with a dark table and chairs, is visible in the background, complemented by a well-equipped kitchen.

Home in The Blue Mountains

4.89 out of 5 average rating, 95 reviews

Rivergrass Oasis: Steps to Blue Mountain Village!

A refreshing swimming pool is surrounded by a paved patio and lush greenery. An umbrella provides shade over an outdoor seating area featuring lounge chairs. The vibrant colors of the landscaping complement the clear blue water, creating a tranquil and inviting outdoor space.

Home in Midland

4.82 out of 5 average rating, 49 reviews

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

Home in The Blue Mountains

4.88 out of 5 average rating, 122 reviews

Blue Mountain Retreat In Historic Snowbridge

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.

4.91 out of 5 average rating, 109 reviews

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

Home in The Blue Mountains

4.94 out of 5 average rating, 209 reviews

Pool Open / Serene mountainside home View/Shuttle

Condo rentals with a pool

Top guest favorite

Condo in The Blue Mountains

4.89 out of 5 average rating, 136 reviews

Blue Mountain Getaway at North Creek Resort

An outdoor swimming pool is surrounded by a wooden deck and clear blue skies. The calm water reflects the greenery from nearby trees. A shaded area with colorful umbrellas provides seating for relaxation, while a fence ensures privacy and safety around the pool area.

Condo in The Blue Mountains

4.81 out of 5 average rating, 204 reviews

Mountainside Escape at Blue - Outdoor Pool

An aerial view reveals a sprawling community of low-rise condos, interspersed with patches of green including a golf course. A swimming pool is visible within the complex, surrounded by a landscaped area. The surrounding hills are dotted with trees, showcasing a range of natural colors.

Condo in The Blue Mountains

4.88 out of 5 average rating, 180 reviews

Close to Village, 2 Bedrooms , Rivergrass

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

Condo in The Blue Mountains

4.93 out of 5 average rating, 305 reviews

Cozy Studio Mountainside stay in Blue Mountains

Top guest favorite

A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.

Condo in The Blue Mountains

4.97 out of 5 average rating, 107 reviews

3 Peaks at Blue Mountains, your luxury staycation!

Condo in The Blue Mountains

4.91 out of 5 average rating, 127 reviews

The Highlands - Patio, Trails & Shuttle to Blue

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, 149 reviews

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

An outdoor swimming pool is framed by a stone patio and surrounded by trees. The pool features clear blue water and a shallow entry. A nearby building is visible in the background, while poolside lounge chairs and a nearby fence outline the area.

Condo in The Blue Mountains

4.84 out of 5 average rating, 415 reviews

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

Other vacation rentals with a pool

Top guest favorite

An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.

Condo in Innisfil

4.98 out of 5 average rating, 55 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

Top guest favorite

A spacious living area features a comfortable couch and coffee table surrounded by decorative plants. Large windows provide ample natural light, framed by light-colored curtains. A stylish chandelier hangs overhead, and a wall-mounted TV offers entertainment options, creating a relaxing and inviting environment.

Condo in Innisfil

5 out of 5 average rating, 70 reviews

Luxury Stay at Friday Harbour Resort Lake Simcoe

A stylish living area features a cozy dark sofa beside a circular coffee table. A large flat-screen TV is mounted against a striped wood accent wall. Soft natural light filters through sheer and blackout window treatments.

Condo in Innisfil

4.98 out of 5 average rating, 81 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Top guest favorite

A rectangular hot tub is set under a wooden pergola, featuring steps leading down into the water. Surrounding greenery and a glass railing provide a sense of openness. Sunlight casts shadows across the stone tiles and water surface.

Condo in Innisfil

4.95 out of 5 average rating, 66 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

Top guest favorite

A modern kitchen features sleek cabinetry and stainless steel appliances, including an oven and refrigerator. A large island with seating for four is present, complemented by a minimalist design. Soft lighting illuminates the space, enhancing the clean lines and organized layout.

Apartment in Innisfil

4.97 out of 5 average rating, 32 reviews

Fantastic 1 Bdrm With A View.

Top guest favorite

Condo in Shanty Bay

4.98 out of 5 average rating, 57 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

Apartment in Innisfil

4.96 out of 5 average rating, 48 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

Top guest favorite

A stylish living area features a soft gray sofa adorned with various decorative pillows in shades of blue. A light wooden coffee table, with a woven basket beneath, is positioned in front. A serene abstract mural in cool tones enhances the calming ambiance.

Condo in Innisfil

5 out of 5 average rating, 51 reviews

Charming 2 Bed/2 Bath at Friday Harbour Resort

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