Waterfront holiday rentals in Oakville

Guesthouse on Lake Ontario Niagara

Unwind at our cozy guest house. Enjoy the direct waterfront views from the living room, bedroom and private Muskoka chairs. We are located along the shore of Lake Ontario amongst the fruit belt of the Niagara region. vineyards, peach, nectarine and plum trees. Shops, Restaurants, and Award Winning Wineries. FREE TESLA charger 🔌 on-site. Free bottle of wine Direct Lakefront OPEN TIMESLOTS JANUARY 14-17 MARCH 1-31 APRIL 1-30, 2026 MAY 1-31, 2026 JUNE 1-30, 2026 JULY 1-30, 2026 AUGUST 1-31, 2026

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)

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!

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.

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.

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.

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.

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.

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.

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.

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 as well as a fully-equipped kitchen and dining area.

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.