
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.

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

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...

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.

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.

Luxury Beach Spa w/ Private Sauna & Oasis Patio!
Escape to the Beach at Friday Harbour Resort in our newest addition to our Spa Getaway Group of professionally designed suites that will take you to a luxury destination close to home! This stunning Miami Boho Beach Hotel type vibe suite is very spacious and boasts 3 fire elements (indoor & Out) and your own private in-suite Sauna! With 2 beds and 2 baths there is plenty of space for a couples, friends or family stay! Make memories that last a lifetime in our most unique experience suites!

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!

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.

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

Toronto Vacation | ➊ The One Toronto Villa
The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

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.

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.

Cozy Country Spring Getaway | HotTub + Fire Pit
Escape to the countryside this spring 🌸 Unwind in the hot tub, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly
Popular amenities for East Gwillimbury rentals with a pool
House rentals with a pool

Walk-out Luxury basement with Gym & Theatre

King Bed, Pool, Gym, Ravine View, Your Getaway!

Vacation Spa Retreat! Sauna, pool, gym

Lost in Hillsdale | 10 mins to Horseshoe Valley

Countryside walk-out with pool.

Luxury Family Home Indoor Pool Hot Tub Lake Access

The Ridge Roost - Uxbridge Township

Ski, Swim, Soak, Boat & Golf
Apartment rentals with a pool

Beautiful Condo Across CN Tower and MTCC

The Penty: Luxurious Penthouse with Pool, Hot Tub

Luxury 1+Den condo steps away from CN Tower & Lake

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Stylish Downtown Toronto Condo Free Parking | FIFA

Exceptional 2+1 ground floor condo @Friday Harbour

Friday Harbour Luxury Condo Escape, Sleeps 4

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Other holiday rentals with a pool

FH Penthouse | Luxury 4-Bed | Pool & Hot Tub | BBQ

Bright and Airy Guest Suite with Pool

Cozy Residence with Walkout to Courtyard

Charming 2 Bed/2 Bath at Friday Harbour Resort

Amazing Pool at 4BR/3WR Cottage + Close By Beaches

5-Acre Waterfront Cottage w/sauna & Hot Tub

Charming 3-Bedroom Lake Front Cottage with Pool

Hidden Gem of Thornhill (Ravine+Pool+Hot tub)
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 $38 SGD per night before taxes and fees

Verified guest reviews
Over 170 verified reviews to help you choose

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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- Rentals with outdoor seating East Gwillimbury
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- Rentals with a fireplace East Gwillimbury
- Rentals with a patio East Gwillimbury
- Flat rentals East Gwillimbury
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- Family-friendly rentals East Gwillimbury
- Rentals with beach access East Gwillimbury
- Rentals with a hot tub East Gwillimbury
- Rentals with a firepit East Gwillimbury
- Rentals with a washing machine and dryer East Gwillimbury
- House rentals East Gwillimbury
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Snow Valley Ski Resort
- Trinity Bellwoods Park
- Mount St. Louis Moonstone
- Financial District
- Massey Hall
- Casa Loma
- Downsview Park
- Dufferin Grove Park
- Lakeridge Ski Resort




