
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.

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.

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 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

Spacious 1-br w jacuzzi at Horseshoe Valley
Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Spacious Hideaway in Nature
Welcome to the charming Shanty Bay area! Embrace the relaxed vibes surrounded by natural beauty. Enjoy leisurely walks by Lake Simcoe or explore nearby parks like Oro-Medonte Rail Trail. Discover local shops and eateries, or indulge in water activities and outdoor adventures. Our cozy Airbnb accommodates 4 guests, with a king-size bed and comfy couches. Experience the best of both worlds - a laid-back getaway and exciting local attractions.

Bohemian Luxury at Friday Harbour Resort Simcoe
Welcome to a Bohemian Paradise in the Heart of Friday Harbour. Treat yourself to a relaxing experience only 1hr from Toronto. This beautifully designed condo was designed to make your experience at Friday Harbour the best it can be. **Convenience** One of the few condos with direct walkout to the courtyard’s Firepit and BBQs. Steps away from Restaurants, Nature Trails, Beach & Boardwalk, Golfing, Live Music Events every Weekend.

Pet-friendly, 1 BR condo in Horseshoe Valley
All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Hidden gem in Humber bay shores Toronto w/ parking
Welcome to the cities best kept secret! Enjoy your stay at this luxurious 1 bedroom condo located in the most prestigious and sought-after area in the city. RIGHT ACROSS OF CIRQUE DU SOLIEL 2023
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

2 Bd Boardwalk Condo Patio Oasis

Home away from home with a hot tub and pool

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

Cozy Heated Pool House in Newmarket

Luxury Family Home Indoor Pool Hot Tub Lake Access

The Ridge Roost - Uxbridge Township
Condo rentals with a pool

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

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

Luxury 1BD Condo w/ Stunning Views - Toronto

Luxury Downtown Condo For 4 (CN Tower Views)

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Friday Harbour Luxury Condo Escape, Sleeps 4

Exceptional 2+1 ground floor condo @Friday Harbour

Stylish 1BR/2 bed CN Tower view, Free Parking
Other holiday rentals with a pool

The Snug Oasis - Burrow (Near Airport)

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

Chic Richmond hill Condo

Trendy 1 Bdrm w/Pool & Hot Tub View

Cedar Escape • Sauna • 10-Acre Private Forest

Cozy Entire 2 Bedrooms Suite - Good Location

Charming 2 Bed/2 Bath at Friday Harbour Resort

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool
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 $42 AUD per night before taxes and fees

Verified guest reviews
Over 170 verified reviews to help you choose

Wi-Fi availability
10 of East Gwillimbury holiday 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!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Island of Montreal Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Laurentides Holiday rentals
- Fitness-friendly rentals East Gwillimbury
- Family-friendly rentals East Gwillimbury
- Rentals with a fire pit East Gwillimbury
- Private suite rentals East Gwillimbury
- Rentals with outdoor seating East Gwillimbury
- Waterfront rentals East Gwillimbury
- House rentals East Gwillimbury
- Rentals with lake access East Gwillimbury
- Rentals with a hot tub East Gwillimbury
- Rentals with a washing machine and dryer East Gwillimbury
- Rentals with a patio East Gwillimbury
- Pet-friendly rentals East Gwillimbury
- Rentals with beach access East Gwillimbury
- Rentals with a fireplace East Gwillimbury
- Apartment rentals East Gwillimbury
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- Distillery District
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Massey Hall
- Financial District
- Mount St. Louis Moonstone
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Wasaga Beach Area




