Vacation rentals with a pool in Milton

Cozy HotTub & Fireplace - 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!

Sleeps 12 ADULT private hot tub pool Walk to Lake

Max 12 ADULTS* - Price VARIES with # of guests*. (Add correct # for price accuracy.) - Cottage Vibe, Cozy, secluded - POOL mid-June to October - HOT TUB open all year - Ping pong/pool table - AC/furnace. NEW! - BBQ + fuel - Private entrance - Short walk to the lake - Towels: Provided (guests bring beach towels). *ADULTS ONLY. Unfenced pool = RISK to toddlers/non-swimmers. **No parties, events, unregistered guests. ** Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

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.

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

Alpaca farm stay and bunkie getaway.

A farm stay on your way to soaking up all that our county has to offer. The bunkie is located next to a restored century barn and an outdoor pool. The property is home to 5 alpacas, mini goats, chickens and our family dog. The bunkie is on a shared property with our home. It's 1 hour from Toronto, 20 minutes from Hamilton, 1-hour from Niagara-on-the-lake and 10 minutes from the historic Ancaster village. Antiquing, hiking, nature tours, golfing, wine tours, farmers markets and more close by.

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!

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Luxury Oasis with Hot Tub/Pool

Forget your worries in this spacious and serene space. Our space offers you the chance to get away from it all with luxurious extras from a romantic soak in our hot tub or swim in our seasonal pool. Spoiled with robes to use during your stay, or a coffee at our coffee, tea, and hot chocolate bar. Enjoy a romantic fire under the stars in a shared firepit, or relax in your beautiful patio area with your own bbq and beautiful outdoor lighting.

Backyard Oasis Guesthouse.

POOL IS CLOSED TILL MAY 2026 Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

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.