
Vacation 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.

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!

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...

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private 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! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

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.

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

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.

Farmhouse Guest Suite; Year round hot tub
Unique Farmhouse stay in modern Guest Suite Fully stocked kitchenette Bedroom/Livingroom Suite - sleeps 4 Ensuite bathroom with shower Wrap around porch for a glass of wine or your morning coffee. Year round hot tub. Firepit - toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in all months. 1 QUEEN BED 1 QUEEN PULL OUT COUCH Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

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

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!

Aquarius bldg @ Friday Harbour 1st fl 2 bdr/2 bath
Main floor 2 bdr 2 bath condo in Aquarius building 825 sq. ft of indoor space. With a seasonal pool available . Enjoy a luxurious stay at an all season resort at Friday Harbour. We are Steps away from marina, beach, boardwalk, trails and more. Plenty of outdoor activities to enjoy all year round. Our fully furnished condo is ready for you and your guests to enjoy. Outdoor patio to catch fresh air & a cozy, stylish indoor space to unwind and enjoy.

King Bed*Pool*Fireplace*BBQ*Smart TV
The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! 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
Popular amenities for East Gwillimbury rentals with a pool
House rentals with a pool

2 Bd Boardwalk Condo Patio Oasis

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

Home away from home with a hot tub and pool

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

Cozy Heated Pool House in Newmarket

Year-Round Heated Pool & Hot Tub Family Oasis

Countryside walk-out with pool.

Luxury Family Home Indoor Pool Hot Tub Lake Access
Condo rentals with a pool

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

Downtown Markham Unionville

The Penty: Luxurious Penthouse with Pool, Hot Tub

Luxury 2BR - Subway/Pool/Gym/Sauna + Free Parking

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Large & Bright 2BR+Den in Midtown w/ Free Parking

Charming 2 Bed/2 Bath at Friday Harbour Resort

Marina view at Friday Harbour 2bd/2bth Pool option
Other vacation rentals with a pool

Nature trail views with cozy patio and firetable!

Luxurious Friday Harbour Condo

Private 1 bed/1.5 bath in-law suite in a house!

Bright and Airy Guest Suite with Pool

Trendy 1 Bdrm w/Pool & Hot Tub View

Perfect 2 bedrm resort style unit Getaway-Top Host

Beautiful 2 Bed/2 Bath Condo, Private Balcony

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool
Quick stats about vacation rentals with a pool in East Gwillimbury

Total vacation rentals
Explore 10 vacation rentals in East Gwillimbury

Nightly prices starting at
East Gwillimbury vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of East Gwillimbury vacation 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 pools Ontario
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- Rogers Centre
- CN Tower
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- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
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- Toronto Zoo
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- BMO Field
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- Massey Hall
- Financial District
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- Snow Valley Ski Resort
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