
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...

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.

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.

Hillside Haven: Serene Studio Retreat for 4
Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

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

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!

King Bed, Pool, Gym, Ravine View, Your Getaway!
Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

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

Cute and Cozy House

newly renovated, close to airport, washer/dryer

Home away from home with a hot tub and pool

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

The Ridge Roost - Uxbridge Township
Apartment rentals with a pool

Cozy Stays – Your Fall Getaway at Friday Harbour

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

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

Friday Harbour Ground Floor w/ Large Terrance

Downtown Markham Unionville

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

Luxury Condo w. Pool @ Yorkdale, Free Parking!

Exceptional 2+1 ground floor condo @Friday Harbour
Other holiday rentals with a pool

1 Bedroom Suite

Modern luxurious 2 Bedroom With Den

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

Charming 2 Bed/2 Bath at Friday Harbour Resort

Country 1-bedroom unit

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

Luxury Midtown Condo with Pool and Gym, Parking

1Bd+ Den Cozying Apartment in Midtown Toronto
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 £22 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!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Island of Montreal Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Laurentides Holiday rentals
- Rentals with outdoor seating East Gwillimbury
- Rentals with a washing machine and dryer East Gwillimbury
- Family-friendly rentals East Gwillimbury
- Rentals with a firepit East Gwillimbury
- Private suite rentals East Gwillimbury
- Waterfront rentals East Gwillimbury
- Rentals with beach access East Gwillimbury
- Rentals with a hot tub East Gwillimbury
- Fitness-friendly rentals East Gwillimbury
- House rentals East Gwillimbury
- Rentals with lake access East Gwillimbury
- Pet-friendly rentals East Gwillimbury
- Rentals with a patio East Gwillimbury
- Flat rentals East Gwillimbury
- Rentals with a fireplace East Gwillimbury
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Snow Valley Ski Resort
- Toronto City Hall
- Rouge National Urban Park
- Christie Pits Park
- Royal Ontario Museum
- Mount St. Louis Moonstone




