Holiday rentals with a pool in Caledon

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 383 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...

Guest house in Orangeville

4.96 out of 5 average rating, 356 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.

4.95 out of 5 average rating, 105 reviews

Home in Scarborough

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

Loft in Niagara-on-the-Lake

4.89 out of 5 average rating, 408 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Guest suite in Orangeville

4.92 out of 5 average rating, 767 reviews

HotTub & Pool Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

4.96 out of 5 average rating, 163 reviews

Flat in Ariss

Rural Retreat, near to Elora

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

4.95 out of 5 average rating, 308 reviews

Cabin in Mono

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, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

4.99 out of 5 average rating, 179 reviews

Flat in Newmarket

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.

4.99 out of 5 average rating, 174 reviews

Farm stay in Essa

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!

4.95 out of 5 average rating, 103 reviews

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

4.88 out of 5 average rating, 114 reviews

Cabin in Fergus

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

Cabin in Rural Flamborough

4.98 out of 5 average rating, 143 reviews

The Fox's Retreat - A Cozy Cabin for Two

Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.

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Popular amenities for Caledon rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 40 reviews

Home in Mono

Country Family Getaway with Pool and Trails

KatherineRating, 5 stars1 week ago

Michael and Kim were exceptional hosts. We really enjoyed our stay at their beautiful home and property. We especially enjoyed the beautiful sunroom where we had all our meals. Thank you so much!

Home in Niagara-on-the-Lake

4.87 out of 5 average rating, 45 reviews

Vineyard Estate by the River with Pool!

SarahRating, 5 stars4 weeks ago

This property is stunning! It has beautiful views of the vineyard and great walking trails. Plenty of storage and closet space, comfortable beds, the house is very spacious and perfect for a couples getaway. The local wineries looked beautiful, unfortunately we didn’t have time to visit any of them. Short distance into town with some great boutiques and art galleries.

4.96 out of 5 average rating, 24 reviews

Home in Mississauga

Luxury House with a Bright Sunroom & a heated pool

MargieRating, 5 stars5 days ago

A perfect spot for a large group! The pool was great and the common space was large and comfortable! Bedrooms were good size and beds were comfy! Our host was gracious and even brought a birthday cake for my husband. Would definitely stay again!

Home in The Blue Mountains

4.89 out of 5 average rating, 225 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

PamelaRating, 5 stars3 weeks ago

Visited with 4 couples for a few nights away. Beautiful location. Would recommend

5 out of 5 average rating, 13 reviews

Home in North York

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars2 weeks ago

My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!

4.93 out of 5 average rating, 220 reviews

Home in Port Perry

Home away from home with a hot tub and pool

CourtneyRating, 5 stars1 week ago

lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

4.79 out of 5 average rating, 14 reviews

Home in Brampton

Cheerful 3 Bedrooms Available for Renting!

GaneshRating, 5 stars9 months ago

My family and I love traveling and finding unique places to stay and this is definitely my favorite of them all . Ankush’s home was just breathtaking from the spacious bedrooms (especially the master bedroom with the tub) to the giant kitchen, the family oriented living room, a private office, the perfect medium size pool in the back yard that can be set to the right temperature of your choice, a yard big enough for a bbq and chill under the patio. What I love about this home, is I felt secure not just with the home but the area, everywhere on the outside, the neighborhood had cameras. We stayed from the 5-11september 2024 . We checked out 3am in the morning on our way to the airport everything was going wrong . The kids were fussy, flight delayed, it was just stressful. At 5am I picked up the phone and call Ankush to ask if the house was available for one more day,he said yes . With his prompt response we stayed till the 15th. Ankush Thanks for everything. Sure will be back!!

4.55 out of 5 average rating, 11 reviews

Home in Mono

Luxury Hockley Estate Spa

ScottRating, 5 stars2 weeks ago

It was a great location and hosted a large group. Very nice place in a remote area, giving us the feeling of an outdoor oasis.

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Apartment rentals with a pool

4.89 out of 5 average rating, 245 reviews

Apartment in Oro

Spacious 1-br w jacuzzi at Horseshoe Valley

VarleyRating, 5 stars3 weeks ago

Great place to stay for a week….all the amenities, very quiet and quick access to The 400. Recommended highly

4.8 out of 5 average rating, 104 reviews

Apartment in North York

Chic Studio w/ Pool | Near Lawrence West Subway

KayodeRating, 5 stars1 day ago

Andrews Place is perfect for a solo traveler. The property is clean, private, and offers excellent transport access to very interesting places. You can catch a direct bus from Toronto YYZ Airport with no need to change buses, and it's just less than a 10-minute walk to the property from the bus stop. It was truly great value for money.

5 out of 5 average rating, 86 reviews

Apartment in North York

The Penty: Luxurious Penthouse with Pool, Hot Tub

Lilia SaloméRating, 5 stars1 week ago

Amazing place, besides the location, the apartment was very nice to enjoy Robert was very helpful and responded fast

4.93 out of 5 average rating, 152 reviews

Apartment in Toronto

Hidden gem in Humber bay shores Toronto w/ parking

RebeccaRating, 5 stars1 month ago

Super convenient area for getting around the city. Very clean and super friendly host.

4.89 out of 5 average rating, 143 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Tanuja KajalRating, 5 stars2 weeks ago

We had an amazing time at Kevin’s place! It was the perfect peaceful getaway from the city. The home was clean, comfortable, and exactly what we needed to relax and unwind. Kevin was a great host—very responsive to messages and incredibly accommodating, even allowing us a late check-out which we really appreciated. He provided clear and detailed instructions for accessing the place, which made everything smooth and easy. Thank you, Kevin, for being so thoughtful and welcoming. We’d definitely love to come back again!

Apartment in Downtown Toronto

4.92 out of 5 average rating, 277 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

NicoRating, 5 stars6 days ago

Great place, extremely close to CN Tower and Roger’s Stadium and check in was really easy with clear instructions for check in/check out

4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

VictoriaRating, 5 stars1 week ago

Loved this place so much! Shai was amazing. Definitely will be coming back!