Oakville vacation rentals

4.79 out of 5 average rating, 115 reviews

The exterior of the lake house shows multiple levels with wooden balconies overlooking the water. A stone patio borders the edge of the lake, providing direct access to the shoreline. The soft glow of lights can be seen through the large windows, hinting at a welcoming interior.

Home in Hamilton

Modern Waterfront Villa | Hot tub, Kayak

Experience lakeside living with unobstructed views of Lake Ontario and the Toronto skyline. This spacious and modern-styled lake house boasts a private balcony, perfect for savoring morning coffee or sunsets over the water. With direct lakefront access, enjoy summer on the water right at your fingertips. Hot tub Stunning views Wine fridge BBQ 4 luxurious queen beds Walk to the nearby Fifty Point Conservation Area Short drive to nearby wineries 30 min drive to Niagara Falls & Niagara-on-the-Lake

A spacious rooftop terrace features modern lounge seating and dining areas, offering panoramic views of the city skyline. Lush greenery and a barbecue area enhance the outdoor experience, providing a peaceful retreat above the bustling city.

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

4.99 out of 5 average rating, 143 reviews

A spacious bedroom features large windows that provide a clear view of the surrounding trees and outdoor park area. A shelf with books and decorative items displays alongside a small table adorned with seasonal decorations, creating a calm and inviting environment.

Home in The Beaches

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Guesthouse in Hamilton Beach

4.84 out of 5 average rating, 200 reviews

Hamilton Beach Guesthouse with guest Kayaks

LAKEFRONT* renovated lakefront small cottage with two Kayaks situated on the Hamilton Waterfront beach trail. Enjoy fantastic views of the Toronto Skyline and secluded sandy beach. Relax on large deck, overlooking the lake. Right on the waterfront trail, roller blade, bike, kayak or enjoy the sandy beach. Very central for a Niagara winery and Toronto trip. Includes: Smart TV, 1 Parking spot, Tetherball, good Wi-Fi, Fire-pit , BBQ, Kayaks Queen size bed Coffee, condiments &cooking ingredients

4.92 out of 5 average rating, 205 reviews

A comfortable outdoor seating area showcases two white cushioned chairs and a sofa, arranged around a glass-top table. A decorative plant and small vase complement the setup. The background reveals a scenic view of the lake and shoreline, under a partly cloudy sky.

Home in Hamilton Beach

Beautiful Renovated Beach Cottage Home

When you enter our immaculately clean Beach Cottage home you will feel like you are at a boutique hotel. Beautiful white linens and towels, WIFI, smart TV, Keurig coffee machine and more. Choose to have a BBQ with friends and family on one of our two decks as you watch the Sunset from Lake Ont. Take a stroll or a bike ride down the Beautiful boardwalk or visit the beautiful beach all located at the end of our yard. Whether you are here for business or pleasure there is something for everyone!

4.85 out of 5 average rating, 158 reviews

A living area features a light-colored sofa alongside a dark blue sectional. A round coffee table sits on a patterned rug. Large sliding glass doors allow natural light and views of the outdoor space with wooden decking and vibrant scenery.

Cottage in Hamilton

Lakeview Oasis: EV Charger, Fire Pit, Sunset View

Relax in our tranquil Lake Ontario retreat, nestled in Stoney Creek between Toronto and Niagara Falls. Our cottage boasts lake views year-round, a backyard oasis with a fire pit, outdoor furniture, and yard games. Indoors, enjoy recent renovations including billiards, ping pong, Smart TV, and board games. Sleeps six with two bedrooms and a sofa bed, fully-equipped kitchen, modern bathroom, laundry, free Wi-Fi, and parking. Create unforgettable memories in our cozy and tastefully decorated home.

Guest suite in Burlington

A wooden deck is highlighted with comfortable seating arrangements surrounded by vibrant planters filled with greenery. A patterned rug adds texture to the outdoor space, complemented by a table featuring a floral centerpiece. Soft lighting fixtures are positioned at the edges for ambiance.

4.94 out of 5 average rating, 132 reviews

Burlington core close to lakefront and downtown.

Large bright lower level walkout 3 bedroom in quiet residential neighborhood within walking distance to downtown and lake. Plenty of greenspace and deck and parking. Brand new kitchen fully stocked including oil spices tea coffee. Separate entrance with self-check in. Own free laundry facilities. Close to beach, promenade, festivals, trails, restaurants, shopping and more. 45 mins to Niagara Falls and Toronto. Wi-Fi, freezer, cable, Netflix included. 3 piece bathroom and unlimited towels.

4.85 out of 5 average rating, 102 reviews

An outdoor patio area is displayed with various seating options, including lounge chairs and a dining set. A large umbrella provides shade, while a fire pit is surrounded by additional seating. The lake is visible in the background, framed by greenery.

Home in Hamilton Beach

Beachfront Escape | Lakeview deck, Hot Tub, Games

Beachfront living at its finest! Enjoy direct beach access, captivating lake views from the deck, BBQ feasts, fun games, hot tub, and relaxing around the fire pit. Inside, find a tastefully arranged 4-bedroom space for 10 guests, a the cozy living room, with a large TV, including a main floor bedroom with an ensuite. The upper floor offers three additional rooms for ultimate comfort. A fully-equipped kitchen and dining area. Experience Hamilton Beach with us & learn more below!

4.95 out of 5 average rating, 281 reviews

Home in Port Dalhousie

Nautica Beach House on Lake Ontario

License 23 110691 STR. Enjoy extraordinary sunsets and views of Lake Ontario and the Toronto Skyline while sitting in comfortable Muskoka chairs around a fire pit, enjoying a cup of coffee or a glass of wine. My home offers high-speed internet, multiple Smart HD TVs, indoor fireplace, 2 outdoor fire pits, and a large backyard with stairs leading to a Private Beach. Just a short walk to Lakeside Beach, downtown Port Dalhousie, and a short drive to Niagara wineries!

4.92 out of 5 average rating, 117 reviews

A cozy outdoor seating area features comfortable gray wicker furniture arranged around a wooden deck, with decorative flower boxes enhancing the backdrop. Surrounding greenery provides a serene atmosphere, complemented by clear blue skies and a nearby heating element for cooler evenings.

Apartment in The Beaches

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

4.93 out of 5 average rating, 299 reviews

A bright living area features large glass windows offering expansive views of the lake. Natural light fills the space, complemented by a light-colored couch and modern coffee table. The adjacent patio doors lead to an outdoor deck, enhancing the connection to nature.

Home in Lincoln

Amazing Lake-Front Retreat!

HIGHLIGHTS: - Priceless lake views that changes every day - Amazing wineries, Niagara attractions nearby - Hot tub - Lake access - Kayaks to explore the lake - Deck with BBQ - Putting green - Luxury boat rental to cruise the lake - Smart TVs (Netflix included) - Ping pong, air hockey - Clean linens, towels + surfaces disinfected to ensure guests have a clean and comfortable stay ** Please review the "Other details to note" section prior to booking **

Bungalow in Hamilton Beach

A spacious swimming pool is surrounded by a solid stone deck. The water glimmers under sunlight, reflecting the clear sky above. Lounge chairs are positioned nearby, with a shaded area visible in the background. The setting invites relaxation and leisure.

4.94 out of 5 average rating, 157 reviews

Lakefront. Pool. Beach. Fire-pit.

A PERFECT COMBINATION OF LOCATION, LUXURY AND LIFESTYLE. This unique, self contained Studio is only steps from the beach and the beach trail. Enjoy unforgettable beach sunrises. This exclusive beach-sand-bar community is centrally located between Toronto and Niagara. It's a hop, skip & a jump to world renowned restaurants, art crawls, fashion, theatre, culture & more. ADULTS ONLY (21>). Long weekends have a 3 night min.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oakville vacation rentals

Laptop-friendly workspace

Stay near Oakville's top sights

St. Louis Bar & Grill71 locals recommend

Oakville Place22 locals recommend

Whole Foods Market4 locals recommend

Fortinos35 locals recommend

Metro3 locals recommend

Cineplex Cinemas Winston Churchill9 locals recommend

Oakville apartment rentals

A spacious living area features light wood flooring and large windows that allow natural light to fill the room. A comfortable sofa is positioned near a sleek entertainment unit, while a dining table with chairs is visible in the background.

4.79 out of 5 average rating, 61 reviews

2-Bedroom Apartment in Downtown Toronto!

Apartment in Streetsville

A spacious bed is positioned against a neutral wall, complemented by two dark blue pillows and a soft gray blanket. A neatly folded towel set is placed at the foot of the bed, while a small nightstand stands beside it, adding functionality to the room.

4.68 out of 5 average rating, 19 reviews

Fully Furnished 2 Bedroom Apartment

4.78 out of 5 average rating, 114 reviews

A modern living room features a sleek brown sofa with tufted design, positioned against a light-colored wall. A glass side table is located next to the sofa, and a soft green area rug complements the decor. Natural light softly illuminates the space.

Apartment in Dixie

1 Bedroom Apartment with spacious living room

4.82 out of 5 average rating, 202 reviews

A cozy corner is featured, showcasing a patterned sofa with two gray cushions beside a glass table. A flat-screen television is positioned in front of the seating area. A framed artwork of tulips adds a touch of decor to the wall, enhancing the neutral tones of the room.

Apartment in Caledon

Basement for Rent Bolton South Hill

4.94 out of 5 average rating, 157 reviews

A cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.

Apartment in Midtown

Cute Private Apartment near University of Toronto

4.95 out of 5 average rating, 65 reviews

The spacious open-concept living and dining area features a sectional sofa with decorative pillows, a dining table with chairs, and a wall-mounted television. Light-colored walls and warm flooring create a welcoming environment, while artwork adorns the walls, enhancing the contemporary design.

Apartment in Mississauga

Spacious, Private & Secure 1 Bdrm Apt near Airport

4.85 out of 5 average rating, 137 reviews

A modern living area features a comfortable gray sofa with a patterned accent cushion. A round dining table with matching chairs is positioned opposite the sofa. Light streams through two windows, complemented by soft green walls and a flat-screen TV mounted on the wall.

Apartment in Leslieville

Stylish 2BR Suite in Leslieville with Parking!

Apartment in Davisville Village

An open living space is visible, featuring a large leather sofa and a glass coffee table. A modern kitchen equipped with high-end appliances is adjacent, complemented by a round dining table with four stylish chairs. Natural light brightens the area.

4.95 out of 5 average rating, 136 reviews

Midtown modern 1 bedroom suite

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Other great vacation rentals in Oakville

An open kitchen and living area is presented, featuring sleek, modern cabinetry and appliances. A dining table with seating for four is visible, alongside a black leather couch. Natural light filters through large windows, highlighting the warm wooden flooring and decorative green plants.

5 out of 5 average rating, 6 reviews

The Snug 1+1 Suite w/ Free Parking

Home in Churchill Meadows

The exterior view features a modern two-story house with a stone facade and a welcoming front porch. A neatly landscaped yard with shrubs and a tree provides a touch of greenery. The double garage doors are prominently displayed, complementing the home's elegant design.

4.9 out of 5 average rating, 41 reviews

Holiday retreat in Toronto

4.75 out of 5 average rating, 4 reviews

The kitchen features modern cabinetry and a sleek countertop made of speckled granite. Stainless steel appliances include a refrigerator, oven, and dishwasher. A coffee maker is positioned for easy access, and natural light filters through the window above the sink.

Home in Brampton

My Charming Getaway

The spacious living area features large windows offering city views, complemented by a modern sofa and a dining table for four. A decorative floating planter hangs above, while a concrete accent wall adds texture. A partition leads to the cozy bedroom, visible in the background.

4.83 out of 5 average rating, 42 reviews

Jungle Made of Concrete: Free Parking & City View

A modern living area features a cozy gray sofa adorned with soft cushions and a textured throw. A sleek entertainment center holds a 55" smart TV. Large windows provide panoramic views of the city, while light streams in, creating a bright atmosphere.

5 out of 5 average rating, 13 reviews

Bright & Stylish Suite | Prime Location + Parking

4.95 out of 5 average rating, 58 reviews

A modern kitchen features sleek white cabinetry and a dark granite countertop. Stainless steel appliances, including an oven and refrigerator, are visible. A small dining area is included, with a blue chair positioned beside a circular glass table. Warm lighting enhances the clean design.

Apartment in Hamilton

Brand New Luxury 2BR apartment in Hamilton

4.95 out of 5 average rating, 22 reviews

A modern bathroom features a spacious walk-in shower enclosed by glass panels, complemented by white marble walls. A double vanity with sleek dark cabinetry and a large mirror provides ample storage and surface space. Soft lighting enhances the clean and fresh appearance.

Townhouse in Mimico

Modern Toronto Townhome by the Lake - Free Parking