Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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

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Guest favorite
The living area presents a spacious layout, featuring a white sofa and a glass coffee table. A large television is mounted on the wall. Decorative glass vases in teal shades are placed nearby. Natural light filters through the open space, creating a welcoming ambiance.
Condo in Oakville
4.91 out of 5 average rating, 102 reviews

LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!

NEW GORGEOUS LUXURY CONDO WHEELCHAIR ACCESIBLE. *** NEW BED in 2nd!*** PRIME BEDROOM has a queen size memory foam mattress & a desk. SECOND BEDROOM has a brand new bed with double mattress medium/firm and a working desk, now accessible to guests. 2 FULL BATHROOMS: The en-suite has has a step up shower and a Bidet. SECOND: Has a tub & shower, very spacious. *OPEN CONCEPT LIV. AREA. *OPEN BALCONY. TASTEFULLY FURNISHED, SOFT AND CLEAN COLORS HARDWOOD FLOORS THROUGHOUT EXTRA WIDE HALLS AND DOORS

Top guest favorite
The exterior of a two-level apartment is shown, featuring a wooden deck accessible by stairs. A light brick facade complements large windows, while potted flowers add color to the entrance. Surrounding greenery enhances the inviting atmosphere of the building.
Apartment in Mississauga
4.98 out of 5 average rating, 105 reviews

Cozy apartment with Free Parking !

Centrally located prime location near buss, highway, parks, shopping, groceries, restaurants and movie theater. Minutes from major highway QEW, 35 min drive to Toronto and Airport. It is spacious, 2 level split apartment. Washroom and bedroom on the upper level. TV & Kitchen on the lower level. Kitchen is equipped with fridge, pots, microwave, toaster, air fryer, utensils, coffee maker. Smart TV, Netflix, Wifi, Parking, Private lawndry are all included. Not permitted: pets, smoking, parties.

Top guest favorite
A contemporary kitchen is highlighted by sleek cabinetry and a spacious island with bar seating. Stainless steel appliances, including a refrigerator and oven, are visible. Soft lighting enhances the modern design, and a mirror reflects the lush greenery in the corner, adding depth to the space.
Apartment in Oakville
4.96 out of 5 average rating, 116 reviews

Condo Style Basement in Oakville (Walk Up)

Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers

Guest favorite
Home in Oakville
4.93 out of 5 average rating, 109 reviews

Sun-kissed 3BR family home in a quiet neighborhood

♡ The fastest internet w/ 1Gb download speed ♡ Fully Equipped Kitchen ♡ minutes drive to Sheridan college, Walmart, Oakville Place, lakeshore ♡ 7 min. drive to Trafalgar GO Station, 20 min. to Toronto premium outlets 25 min. to Pearson airport 30 min. to Toronto downtown ♡ Walking distance to convenient store, trails, food, bus stop, library. ♡ Free Parking ( 2 Spots) ♡ Automated Check in & Check Out ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ❤ Book today!

Guest favorite
A modern kitchen area features stainless steel appliances and dark wood cabinetry. An island with bar stools invites casual dining. Soft lighting is complemented by natural light streaming through a large window, with a view of greenery outside.
Condo in Oakville
4.91 out of 5 average rating, 23 reviews

1 BR Boutique Charm, Urban Calm!

Experience modern living in our boutique one-bedroom, private apartment in the heart of Oakville. This stylish 750-square-foot unit blends contemporary elegance with urban charm, offering a cozy retreat. Located in the vibrant Dundas/Trafalgar area, it includes underground parking, high-speed internet, and fully equipped kitchen and bathroom. Just steps from public transport, shops, and grocery stores, this ground-floor unit offers easy access from both inside the building and street level.

Guest favorite
A modern bedroom features a spacious bed with a grey quilt and coordinating pillows. A small nightstand is placed beside the bed. A white desk and ergonomic chair provide a work area, with natural light filtering through dual-layer window shades.
Home in Oakville
4.91 out of 5 average rating, 23 reviews

Spacious Private Suite | King Bed

Relax in a spacious, private suite in a newly built home. This modern retreat features a comfortable king bed, a walk-in closet, a private bathroom, and a office work area. A kitchenette is also available for your convenience of making light meals and drinks. Located in a great area, you'll be just minutes from shopping, dining, and grocery stores, making it easy to meet all your daily needs. Feel free to reach out with any questions about the suite or the neighbourhood—I’m happy to help!

Top guest favorite
A cozy living area features a light grey sofa and a plush dark blue chair, arranged around a small white TV stand facing a flat screen television. A decorative rug covers the floor, and a dining table with two chairs is positioned nearby, complemented by a vase of flowers.
Apartment in Oakville
4.99 out of 5 average rating, 139 reviews

Bright, Spacious, Quiet 2 bedroom - Licensed

Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

Top guest favorite
A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.
Home in Oakville
4.89 out of 5 average rating, 174 reviews

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ

Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

Top guest favorite
A private hot tub is situated on a rooftop terrace, surrounded by privacy screens. Soft lighting is positioned around the area, creating an inviting ambiance. Steam rises gently from the hot tub's surface, hinting at a warm and relaxing experience.
Home in Oakville
4.98 out of 5 average rating, 120 reviews

Modern Executive Townhome w/ Rooftop Hot Tub Oasis

Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Guest favorite
A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.
Home in West Oakville
4.9 out of 5 average rating, 115 reviews

Large Luxury Villa with Swim Spa! Near downtown!

Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

Superhost
A modern studio space is captured featuring a cozy bed adorned with white linen and decorative pillows. A sleek stainless steel refrigerator is positioned nearby, alongside a small wooden table with a potted plant. Natural light filters through a window, enhancing the inviting atmosphere.
Apartment in Oakville
4.79 out of 5 average rating, 139 reviews

Cozy Modern Studio in Oakville | Free Parking

Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails

Top guest favorite
Cabin in Aldershot Central
4.97 out of 5 average rating, 320 reviews

Animal Lovers Dream! Barn Loft in Burlington

Experience life on a tiny farm just outside the city! Stay in our charming and comfortable barn loft and wake up to the sounds of chickens, ducks, geese, pigs, goats and horses and our adorable Highland cows. Spend time watching or interacting with all the very friendly animals that surround the barn. You will meet all the animals as they all come up readily to anyone who visits the farm. Guests are welcome to participate in the morning feeding.

Popular amenities for Oakville vacation rentals

When is the best time to visit Oakville?

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Avg. priceG$17,316 GYDG$17,316 GYDG$17,942 GYDG$17,942 GYDG$19,402 GYDG$21,071 GYDG$21,488 GYDG$21,697 GYDG$19,611 GYDG$19,402 GYDG$19,402 GYDG$18,776 GYD
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Frequently Asked Questions

  • How is the weather in Oakville?

    Oakville experiences a humid continental climate. Summers are typically warm, with temperatures around 82°F (28°C). Winters can be cold, with temperatures often around 23°F (-5°C), and are perfect for winter activities like ice skating. Fall and spring are mild and invite outdoor exploration.

  • What are some of the best things to do in Oakville?

    Oakville is a treasure trove of activities. Explore the beautiful waterfront parks, wander through the Oakville Museum, or stroll through the Royal Botanical Gardens. Don't miss the opportunity to visit the Oakville Galleries for a taste of contemporary art.

  • What is the best time of year to visit Oakville?

    Summer, from June to August, attracts many visitors to Oakville with warm weather and outdoor activities. Popular local events include the Oakville Children's Festival in July and the Downtown Oakville Jazz Festival in August, which bring a festive atmosphere to the town.

  • What are the best places to stay in Oakville?

    You can find a range of accommodation options across Oakville. Downtown Oakville, with its historic charm, shops, and eateries is a popular choice. Bronte Village, known for its waterfront views and vibrant community, is another preferred area. Kerr Village is also appealing with its art galleries and a lively dining scene.

  • What are the best places to visit in Oakville?

    Some popular places in Oakville include the Oakville Lighthouse, Bronte Heritage Waterfront Park, and Gairloch Gardens. History enthusiasts often explore the Oakville Museum, while art lovers enjoy the Oakville Galleries.

  • What are some hiking trails in Oakville?

    For hiking enthusiasts, Oakville has scenic trails. The Waterfront Trail offers stunning lake views, while the Sixteen Mile Creek Trail provides diverse landscapes. The Lions Valley Park also has a network of trails through picturesque woodland.

  • What are some family activities to do in Oakville?

    Families in Oakville can enjoy a picnic at one of the many parks, explore the interactive exhibitions at the Oakville Museum, or take a walk along the Waterfront Trail. A visit to the Bronte Creek Provincial Park, with its outdoor pool and farm, is a popular option for families.

  • What are some of the best day trip ideas in Oakville?

    Consider a day trip to the charming town of Niagara-on-the-Lake, just 65 miles (105 km) away. You could also venture to Toronto, just 25 miles (40 km) away, for an urban adventure. Another popular option is a visit to the Royal Botanical Gardens in nearby Burlington.

  • Are there pet-friendly vacation rentals in Oakville?

    Four-legged friends are welcome in Oakville. Choose from more than 200 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oakville?

    Yes! Work meets play with ease at over 560 vacation rentals in Oakville featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Oakville vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Oakville, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly condo rentals in Oakville?

    Oakville has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Oakville have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Oakville have air conditioning?

    Absolutely! We offer over 50 condo rentals with air conditioning in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Oakville have wifi?

    Absolutely! We offer over 40 private suite rentals with wifi in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oakville have a gym?

    Absolutely! We offer over 50 apartment rentals with a gym in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in townhouse rentals in Oakville?

    Experience the best of Oakville with our townhouse rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Bungalow Rentals in Oakville?

    Enhance your stay in our Bungalow Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Oakville

  • Total vacation rentals

    Explore 870 vacation rentals in Oakville

  • Nightly prices starting at

    Oakville vacation rentals start at G$2,086 GYD per night before taxes and fees

  • Verified guest reviews

    Over 18,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    430 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 200 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    860 of Oakville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oakville rentals

  • 4.7 Average rating

    Oakville stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore