Holiday rentals in Oakville

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Top-rated holiday rentals in Oakville

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

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Superhost

Home in Hamilton

4.79 out of 5 average rating, 101 reviews

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

Guest favourite

Flat in Downtown Toronto

4.96 out of 5 average rating, 23 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

Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 125 reviews

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.

Guest favourite

Guest house in Hamilton Beach

4.84 out of 5 average rating, 199 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

Guest favourite

Home in Hamilton Beach

4.92 out of 5 average rating, 192 reviews

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!

Superhost

Cottage in Port Dalhousie

4.89 out of 5 average rating, 45 reviews

Beach Cottage

Relax with the whole family at this fully renovated beach cottage. 10 minute walk to public beach, downtown restaurants, ice cream, lakeside park and carousel. Beautiful neighborhood to walk and play in. Short walk to henley island and grandstand. Equipped with all your outdoor dining and entertainment needs. Excellent choice for cozy winter getaways as well! Snuggle up by the fire, take the dog out for a nice hike at the local dog park, ice fish or skate on the Martindale pond minutes away!

Guest favourite

Guest suite in Burlington

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.

Superhost

Home in Hamilton Beach

4.95 out of 5 average rating, 76 reviews

Lakeside Manor | The Ultimate Lakeside Oasis

Welcome to The Lakeside Manor. Truly relax in extravagance, steps from the beach. Enjoy a comfortable California king bed, two queen beds, and plush couch. Experience our overstocked kitchen, large 4 piece bathroom, private balcony with mountain views while overlooking our massive private 16,000sq ft back yard oasis. Enjoy our private parking areas and convenient location close to everything you need! Top restaurants, trails, activities, beach, golf, go cart and more. Great fit for all!

Superhost

Home in St. Catharines

4.8 out of 5 average rating, 54 reviews

Cottage on the water | Hot Tub

Vale Haus A newly renovated home located right across the Twelve Mile Creek. Enjoy your morning coffee with a stunning view from the front or rear decks. Features include a 6 person hot tub, two entertainment room with large smart TVs. Perfect for friends and family 3 BR, and optional pull out sofa for an extra guest. 15 minute drive to Clifton hill and 2 minutes to downtown St. Catharine’s Perfect for a friends getaway with lots of winery’s near by. License Number: 23 103075 STR

Guest favourite

Home in Port Dalhousie

4.95 out of 5 average rating, 268 reviews

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!

Superhost

Holiday home in Hamilton

4.85 out of 5 average rating, 115 reviews

Oasis By The Water, Breathtaking Sunsets and Views

Paradise is Calling you to this Exquisite Getaway! With Breathtaking Indoor And Outdoor Entertainment Areas and Stone Interlock Patio Overlooking Jaw Dropping Views Of Lake Ontario. Catch Incredible Sunrises And Sunsets. Sit By The Cozy Fire With Family And Friends, And Make Memories That Last A Lifetime. High End Finishes With Turkish Stone Throughout and a Gorgeous Custom Kitchen With High End Appliances. 4 Bedrooms Allows For a Variety Of Sleeping Arrangements.

Guest favourite

Flat in The Beaches

5 out of 5 average rating, 25 reviews

Beaches Beauty - Top of the Hill

Perched atop the Beaches tallest hill, this newly renovated, stylish home offers some of the best views the area has to offer. Bathed in natural light, there is plenty of space inside and out, to unwind and relax in your private space. Feel like going out? Have fun with the whole family (including your fur babies!) experiencing all the Beach and trendy Kingston Road Village have to offer in this centrally located gem. We would love to have you as our guest!