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

4.77 out of 5 average rating, 118 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, 46 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

Guest house 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

Guest favourite

Home in Hamilton Beach

4.91 out of 5 average rating, 208 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!

Top guest favourite

Guest suite in Burlington

4.94 out of 5 average rating, 132 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.

Guest favourite

Home in Niagara-on-the-Lake

4.95 out of 5 average rating, 263 reviews

Amazing Wine-Country Retreat w/ Lots of Amenities!

HIGHLIGHTS: -Country home in the midst of vineyards - Renovated and well-appointed house -Tons of great amenities - Hot tub, sauna - pool room, putting green, firepit, basketball, bikes -Stunning sunsets/sunrises - Close to great wineries and Niagara attractions, yet very private - Game room with ping pong/air hockey/smart TVs (Netflix included) - Luxury boat rental -CLEAN linens, towels. surfaces disinfected **Please review the "Other details to note" section prior to booking**

Top guest favourite

Home in The Beaches

4.99 out of 5 average rating, 143 reviews

Heated Pool-tub Open 365 Days

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, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

Guest favourite

Home in Hamilton Beach

4.85 out of 5 average rating, 105 reviews

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!

Top guest favourite

Home in Port Dalhousie

4.95 out of 5 average rating, 283 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!

Guest favourite

Flat in The Beaches

4.92 out of 5 average rating, 119 reviews

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

Top guest favourite

Bungalow in Hamilton Beach

4.94 out of 5 average rating, 158 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.