Holiday rentals with a pool in East Gwillimbury

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in East Gwillimbury

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

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Top guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.
Apartment in Innisfil
4.97 out of 5 average rating, 101 reviews

Cozy Stays – Your Fall 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!

Guest favourite
The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.
Home in Barrie
4.91 out of 5 average rating, 116 reviews

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

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

Guest favourite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 412 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 favourite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono
4.95 out of 5 average rating, 327 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Top guest favourite
The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.
Flat in Newmarket
4.99 out of 5 average rating, 194 reviews

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Guest favourite
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.
Apartment in Innisfil
4.93 out of 5 average rating, 194 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

Superhost
A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.
Cottage in Alcona
4.9 out of 5 average rating, 240 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.

Guest favourite
A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.
Apartment in Innisfil
4.94 out of 5 average rating, 131 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

The Holiday Markets are here, escape to our spacious, furnished, 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy this season with access to walking trails, boardwalk festivities, live music, events and weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Lau

Superhost
An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.
Apartment in Innisfil
4.87 out of 5 average rating, 169 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!

Top guest favourite
A spacious balcony is shown, featuring a fire table surrounded by comfortable seating. An egg swing chair adds a playful touch, while a Weber BBQ is positioned nearby. The scene is enhanced by a vibrant sunset sky, casting a warm glow over the outdoor space.
Apartment in Innisfil
4.96 out of 5 average rating, 136 reviews

Upscale Spa Getaway w/ Private Sauna

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!

Guest favourite
A modern living area features a dark sectional sofa and a round coffee table placed atop a patterned area rug. Large glass doors provide access to a balcony, while light pours in, illuminating the textured wall design. A beige accent chair adds to the inviting space.
Apartment in Innisfil
4.89 out of 5 average rating, 108 reviews

*HotTub*Pool*FirePit*King Bed*

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a year-round hot tub, outdoor pool, 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 → Year Round Hot Tub → Outdoor Swimming Pool

Superhost
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.
Apartment in Innisfil
4.81 out of 5 average rating, 515 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.

Popular amenities for East Gwillimbury rentals with a pool

Quick stats about holiday rentals with a pool in East Gwillimbury

  • Total holiday rentals

    Explore 10 holiday rentals in East Gwillimbury

  • Nightly prices starting at

    East Gwillimbury holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of East Gwillimbury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across East Gwillimbury rentals

  • 4.8 Average rating

    East Gwillimbury stays are highly rated by guests – averaging 4.8 out of 5!

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