Waterfront holiday rentals in Oakville

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Top-rated waterfront rentals in Oakville

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Top guest favourite
A modern living area is highlighted by large windows allowing natural light. A sleek black sectional couch faces a glass coffee table, while a light-colored armchair adds comfort. A wall-mounted TV is positioned for viewing, contributing to a relaxed atmosphere.
Apartment in Entertainment District
4.96 out of 5 average rating, 156 reviews

Spacious 1 Bed + Den + Downtown + Free Parking

Spacious 1 bed+den modern condo located in the heart of downtown. Steps from the lake, parks, recreation centers. Short walk to CN Tower, Union Station, Rogers Center, Convention Center. → FAST WIFI Perfect for WFH, video calls, & streaming → Approx size 620ft² / 57m² → Dedicated Working space → 60" QLED TV → *NEW 2024* Fully equipped kitchen w/ set of cookware → Walking distance to dining & night life option → Minutes away from grocery, liquor stores, & city transit network (94 Transit Score)

Top guest favourite
A spacious living area features a modern leather sofa complemented by a stylish coffee table. A workspace with a desk and chair is present, with natural light streaming in from the window. Decorative elements include wall art and a serene color scheme.
Flat in Hamilton
4.97 out of 5 average rating, 193 reviews

Harbour House

A spacious 2 bedroom apartment in one of Hamilton's best and safest neighbourhoods - The West Harbour. You'll be steps to the Waterfront and Bayfront Park with easy access to nature trails, amazing restaurants, trendy James Street North, and only 5 minutes away from the downtown core. A perfect launch pad for exploration, or to enjoy beautiful Hamilton. Our house is the mid point of Toronto, Niagara Falls and Wine Country, and minutes walk to the GO Train Station. Getting around will be easy!

Top guest favourite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guest house in Lincoln
4.98 out of 5 average rating, 271 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JANUARY 13-FEBRUARY 5 FEBRUARY 8-28 MARCH 1-31 APRIL 1-30 MAY 1-31 Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: Lake & orchards.

Top guest favourite
A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.
Guest suite in Toronto
4.94 out of 5 average rating, 213 reviews

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Top guest favourite
The entrance of the container home is visible, featuring a wooden deck surrounded by trees. A wooden chair and small table offer a cozy seating area. The deck is enclosed by a glass railing, providing an unobstructed view of the natural surroundings.
Farm stay in Lincoln
4.94 out of 5 average rating, 188 reviews

Inn The Orchard, Valley View, Modern Container

Enjoy the sounds of nature when you stay in this unique place. Our newly renovated "Valley View, Container Home" in beautiful Niagara at Inn The Orchard, has been designed with all luxuries of home but created guaranteeing a relaxing atmosphere and simplicity that you'll never forget. We love creating spaces allowing you to escape the city and be surrounded by nature while remaining in the heart of Niagara's Wine Country! Enjoy this unique spot surrounded by fruit orchards on the valley edge.

Top guest favourite
A living area is featured with a pair of black leather sofas, complemented by decorative cushions. A glass coffee table sits at the center, topped with a small vase of flowers. Soft lighting is provided by two table lamps on either side, and a wall-mounted TV is visible.
Guest suite in Burlington
4.94 out of 5 average rating, 156 reviews

Burlington core.Walk to 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.

Top guest favourite
Farm stay in Lincoln
4.99 out of 5 average rating, 136 reviews

Lake View Farm House | Hot Tub | Sauna | Fire Pit

Welcome to our stunning modern farmhouse loft, nestled on a 10-acre farm with breathtaking lake views. This farm stay retreat offers a perfect blend of rustic charm & organic luxury. Our home has an open-concept living space with vaulted ceilings & an abundance of natural light. It also has a hot tub, sauna, deck, patio furniture, gas BBQ, and a lakefront bonfire pit. The farm soil is currently regenerating & we are between crops. Book your escape now & experience the our lakefront farm.

Top guest favourite
A spacious living room is depicted, featuring a light-colored sofa with decorative cushions and a woven throw. A coffee table with a marble-like surface sits in front, alongside a side table supporting a modern lamp. Soft lighting enhances the welcoming ambiance.
Guest suite in Brampton
4.94 out of 5 average rating, 126 reviews

Lake Guest Suit> 15 mins YYZ>private whole place

You will enjoy this newly renovated private space! Located on the edge of beautiful Professor's Lake, a walk-out basement apartment with a separate entrance, spacious living room, bright bedroom, jet shower bathroom, comfortable king-size bed and new kitchen. Everything separated from upstairs. Private access to the lakeside path from the backyard. Enjoy your morning breeze from the lake when you walk around the lake. A lot of natural beauties, birds, fishes, turtles and great lake views.

Superhost
An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.
Tiny home in Acton
4.84 out of 5 average rating, 122 reviews

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private and quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. This trailer is perfect for 2 to 4 adults looking to relax and enjoy the scenery or explore the lake on kayak or fishing in the lake or enjoy some outdoor movies or campfire or under the stars.

Guest favourite
An inviting entrance is framed by two large trees and a wooden structure. A set of steps leads to a wooden deck, adorned with a potted plant. Natural stone borders the area, enhancing the connection to the surrounding greenery.
Barn in Lincoln
4.9 out of 5 average rating, 153 reviews

Contemporary Vineyard Barn on the Water + Hot tub

Relax in Niagara’s wine country and enjoy the tranquility of being in a nature's paradise on the water. A mix of modern architecture and old-world charm makes this stunning century old barn, perched over 16th Mile Creek, an inspired vacation destination and offsite work location. Set amongst vineyards and orchards on an estate minutes from wineries, restaurants and downtown St Catharines, just off the QEW, our industrial chic wine country retreat sleeps 2 adults and 1 child.

Guest favourite
A modern living space features a dark gray sofa adorned with two textured pillows. Above the sofa, a large black and white cityscape photograph complements the stylish decor. A light fixture with a circular design illuminates the area, creating a welcoming ambiance.
Apartment in Fort York
4.88 out of 5 average rating, 171 reviews

Lakeside Downtown Condo for upto 4 ppl

Enjoy a stylish experience at this centrally located place. My ONE BEDROOM PLUS DEN condo comfortably sleeps 4 people and overlooks the lake and is within walking distance to most Toronto attractions ( Budweiser Stage, BMO field, Exhibition Place, Billy Bishop Airport, CN tower, Ontario Place, countless bars, restaurants and venues. During your Stay you will have access to the state of the art facilities such as gym, sauna, pool, roof-top terrace, paid parking on site.

Guest favourite
The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.
Villa in Aldershot Central
4.96 out of 5 average rating, 164 reviews

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

Popular amenities for waterfront rentals in Oakville

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Quick stats about waterfront rentals in Oakville

  • Total holiday rentals

    Explore 10 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 410 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Oakville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.8 Average rating

    Oakville stays are highly rated by guests – averaging 4.8 out of 5!

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