Vacation rentals with a pool in Caledon

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Top-rated rentals with a pool in Caledon

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 213 reviews

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...

Nov 19 – 26

G$25,020 GYD per night

Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Aug 17 – 24

G$31,278 GYD per night

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

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!

Oct 13 – 20

G$22,264 GYD per night

Guest favorite

Farm stay in Essa

5.0 out of 5 average rating, 118 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Oct 18 – 25

G$35,510 GYD per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

G$15,643 GYD per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 106 reviews

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!

May 10 – 17

G$16,755 GYD per night

Guest favorite

Apartment in Ariss

4.97 out of 5 average rating, 110 reviews

Rural Retreat, 1 bedroom suite near Elora

The perfect winter country retreat in Ariss. Relax in the hot tub and watch the birds. Well situated between Elora, Fergus, St Jacobs and Guelph. Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking, biking, snowshoeing, snowmobile trails & Chicopee Ski Resort. King bed, portable crib, shower, kitchenette, seating area, natural light. Swimming pool, hot tub, large backyard, bonfires, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

Mar 11 – 18

G$24,999 GYD per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 272 reviews

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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Apr 23 – 30

G$34,910 GYD per night

Guest favorite

Farm stay in Markdale

4.99 out of 5 average rating, 124 reviews

Experience Country Living at Firefly Ridge

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. Please note DOGS MUST be on a leash when on the property.

Apr 4 – 11

G$29,867 GYD per night

Guest favorite

Guest suite in Grimsby

4.96 out of 5 average rating, 224 reviews

Bright, spacious 2 bedroom apartment

Nestled just below the Niagara escarpment, in the heart of wine country, this is the perfect place to relax after a busy day. A 4 season vacation destination, you will never find a shortage of activities to do in the area. A short drive or bike ride away from numerous wineries, restaurants and hiking. A 5 minute drive to Lake Ontario, and the beach. We are a 25 minute drive to iconic Niagara Falls and a 45 minute drive to downtown Toronto.

Feb 23 – Mar 2

G$20,997 GYD per night

Guest favorite

Condo in Innisfil

4.83 out of 5 average rating, 388 reviews

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.

Oct 16 – 23

G$13,738 GYD per night

Guest favorite

Guest suite in Orangeville

4.97 out of 5 average rating, 139 reviews

Your very own peaceful santuary in nature

Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.

Jul 4 – 11

G$17,387 GYD per night