
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.

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!

Marina view at Friday Harbour 2bd/2bth Pool option
This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

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.

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.

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!

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.

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
Popular amenities for East Gwillimbury rentals with a pool
House rentals with a pool

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

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

Home away from home with a hot tub and pool

Cozy Heated Pool House in Newmarket

Year-Round Heated Pool & Hot Tub Family Oasis

Ravine Paradise ! heated pool and hot tub!

Countryside walk-out with pool.

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

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

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

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

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

Charming 2 Bed/2 Bath at Friday Harbour Resort

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

FH Harbour Flats 2BR 2BA- Every Day is Friday

Downtown Designer Condo
Other vacation rentals with a pool

Friday Harbour Ground Floor w/ Large Terrance

The Snug Oasis - Woodstock (Near Airport)

Chic Richmond hill Condo

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

Bright and Airy Guest Suite with Pool

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Cedar Escape • Sauna • 10-Acre Private Forest

BBQ with Panoramic Harbour Views - Peaceful Escape
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 ﺩ.ﺇ110 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 & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of East Gwillimbury vacation rentals include wi-fi 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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- Family-friendly rentals East Gwillimbury
- Rentals with a patio East Gwillimbury
- Rentals with a fireplace East Gwillimbury
- Rentals with beach access East Gwillimbury
- House rentals East Gwillimbury
- Rentals with lake access East Gwillimbury
- Pet-friendly rentals East Gwillimbury
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- Rentals with a hot tub East Gwillimbury
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- Rentals with a washer and dryer East Gwillimbury
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- Waterfront rentals East Gwillimbury
- Rentals with pools Ontario
- Rentals with pools Canada
- 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
- Harbourfront Centre
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- Toronto Zoo
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
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- Snow Valley Ski Resort
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