Vacation rentals with outdoor seating in Oakville

Condo in Churchill Meadows

A modern living area features a gray sofa adorned with blue cushions. A wooden coffee table sits on a patterned rug, with a large flat-screen TV mounted on the wall displaying content. The kitchen area is visible in the background, equipped with sleek appliances.

4.91 out of 5 average rating, 113 reviews

Entire Condo - 20min from Toronto Airport

This cozy one bedroom, 500 sq. ft., condo is located in the desirable Churchill Meadows area. It’s conveniently located across the street from Erin Mills Mall and within walking distance to all major amenities. You’ll find highway access to be a breeze; HWY 403 is only 1 minute away and the 401 under 10 minutes. Toronto Pearson Airport is a 15 minute drive, and you’ll find yourself downtown Toronto within 25 minutes. My place is perfect for business travelers, solo adventurers and couples.

Apartment in Churchill Meadows

An open concept living area showcases a comfortable sectional sofa and a glass dining table. A spacious bed is visible in the background, complemented by soft lighting. A workspace with two chairs and a TV is positioned nearby, creating a functional and inviting environment.

4.97 out of 5 average rating, 162 reviews

Comfort, Style and Privacy.

Magnificent lower level suite in detached home with private entrance. Located in quiet, family friendly community. This suite has a modern open concept layout with comfortable Queen bed with fresh linens, a 50" TV, huge walk-in closet, private bath with shower bench & relaxing rainhead, plus fresh towels for your whole stay. Living room has sectional, 40" TV, desk & is open concept to a fully equipped kitchen. Laundry access is on the main level by the entrance and is shared with homeowner.

4.98 out of 5 average rating, 110 reviews

A cozy living area features a light grey sofa and a plush dark blue chair, arranged around a small white TV stand facing a flat screen television. A decorative rug covers the floor, and a dining table with two chairs is positioned nearby, complemented by a vase of flowers.

Apartment in Oakville

Bright, Spacious, Quiet 2 bedroom - Licensed

Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.

4.88 out of 5 average rating, 161 reviews

Upgraded 3Bd 2.5Bth House w/ Pool Table & Swing

Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

A private hot tub is situated on a rooftop terrace, surrounded by privacy screens. Soft lighting is positioned around the area, creating an inviting ambiance. Steam rises gently from the hot tub's surface, hinting at a warm and relaxing experience.

4.98 out of 5 average rating, 111 reviews

Modern Executive Townhome w/ Rooftop Hot Tub Oasis

Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Superhost

A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.

4.88 out of 5 average rating, 107 reviews

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms

Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

4.98 out of 5 average rating, 380 reviews

A bright living area features a mid-century style orange sofa positioned against a white wall. Two blue velvet chairs face the sofa, with a natural wood floor adding warmth. Large windows allow sunlight to stream in, and a vintage record player sits beside a decorative fireplace.

Apartment in Hamilton

Vintage Dreams | Mid-Century Design in artsy area

Love is in the details, so we know you’re going to fall madly in love with The Aberdeen. This mid-century gem is dripping with style, comfort and touches that'll make you feel like it was designed just for you. Whether you have plans to stay in and dance barefoot to the record player or cuddle up on the couch to write a bestseller, one thing is sure - the creative vintage vibes of the space, the private outdoor courtyard and the eclectic neighbourhood will leave you inspired.

4.96 out of 5 average rating, 1,037 reviews

Loft in Lorne Park

Waterfront Coach House Loft

This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.

4.97 out of 5 average rating, 283 reviews

A Highland cow with long, shaggy orange fur stands in a small grassy area. Its prominent horns curve gracefully upwards. Nearby, a feeding trough can be seen, surrounded by scattered hay and an out-of-focus image of another cow in the background.

Cabin in Aldershot

Animal Lovers Dream! Barn Loft in Burlington

Experience life on a tiny farm just outside the city! Stay in our charming and comfortable barn loft and wake up to the sounds of chickens, ducks, geese, pigs, goats and horses and our adorable Highland cows. Spend time watching or interacting with all the very friendly animals that surround the barn. You will meet all the animals as they all come up readily to anyone who visits the farm. Guests are welcome to participate in the morning feeding.

A modern kitchen features sleek white cabinetry and a large island with seating for four. Stainless steel appliances are visible, including a refrigerator and microwave. Bright lighting fixtures hang above the island, and a small green plant adds a touch of freshness to the countertop.

4.97 out of 5 average rating, 104 reviews

Elegant 2BR townhouse condo in central Oakville

Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.

4.84 out of 5 average rating, 167 reviews

A backyard oasis features a sun-drenched inground pool surrounded by lush perennial gardens. A stone patio is equipped with shaded lounge areas and outdoor seating, creating an inviting space for relaxation. The two-story house overlooks the pool, complementing the tranquil environment.

Apartment in Milton

Backyard Oasis Guesthouse.

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.