Vacation rentals in Oakleigh

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Top-rated vacation rentals in Oakleigh

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Top guest favourite
Guest suite in Belgrave
4.92 out of 5 average rating, 431 reviews

Take in Valley Views from a Comfortable Guest Suite

Relax in comfort in this elegant, well-situated 1930’s home. Pour a glass of wine, light a fire, and enjoy the fresh air and surrounding forest setting from total privacy in the cosy living room before retiring to the spacious bedroom. Bottom floor of old hills house. Entire ground floor Available when needed. The home is located near Belgrave Township, close to the Puffing Billy railway and just a short drive from the gorgeous towns of Sassafras, Olinda, and Mt. Dandenong. A lovely English-style tavern with live music sits at the end of our quiet street. Killlik Rum distillery is also at the end of the street for food and cocktails. Parking out front on road (cul de sac) Bus stop on corner to access hills towns Belgrave station 10 minutes walk Steps up to the house. Two cats live on property (Buddy & Braveheart) but probably wont impact on guests unless they are cat lovers!

Guest favourite
A welcoming dining area features a light-colored table surrounded by white chairs. A grey sofa extends along one side, complemented by decorative cushions. Natural light filters through the large bay window adorned with balanced blinds, enhancing the cozy ambiance of this open space.
Apartment in Clayton
4.95 out of 5 average rating, 149 reviews

Conveniently located Cosy Apartment

A cosy self contained Unit with separate entrance in a quiet and safe location. Exempt from Vic Govt Tax. Short walk to Monash Medical/Children's Hospital, 2 km to Monash Campus & Heart Hospital. Double Beds in both rooms and BIR's & Ceiling Fans and it's own Central Heating to keep you warm in colder months. Easy access to public transport with bust top on top of the street and 10 mts walk to Huntingdale Station and 10 minutes drive to Chadstone Shopping centre. Unit is connected yet private.

Guest favourite
An open plan living space features wooden floors and high ceilings with exposed beams. A cozy fireplace stands beside a comfortable bed, and a hand crafted kitchen is visible in the background. Natural light filters through wooden blinds, illuminating the space.
Apartment in Armadale
4.92 out of 5 average rating, 333 reviews

Studio 1158

Loft apartment newly renovated tucked away behind High Street; renowned for designer brands, galleries and antique shops. The apartment is sleek, quiet, liveable and maintains total privacy. It is the ideal blend of design and comfort. Perched up looking over a lush garden, this open plan light filled space is equipped with a hand crafted kitchen, a cosy fireplace and a slick bathroom. Close to Lune (croissant), Victor Churchhill, Alberts Wine Bar, Leaf grocery store, and Moby for coffee.

Top guest favourite
A warmly decorated living space features a mix of vintage furnishings, including a green armchair and a vibrant dining table. Bright wall art adds character, while rich wooden accents and original floorboards create a cozy ambiance. Natural light streams in through the adjoining corridor.
Condo in Beaumaris
5 out of 5 average rating, 104 reviews

Bayside on Keys

Welcome to a private, fully self contained, spacious and light 2 bedroom apartment set in a quiet bayside shopping village. Guests have 2 cafes, 2 restaurants, a Foodworks supermarket and bottle shop, tennis courts and a bowling club just steps away. There's plenty of free unlimited all day parking nearby. too. Located an easy 25km drive to the CBD, a stone’s throw from the cliffs of Port Phillip Bay, 3kms to Royal Melbourne Golf Course and a short walk to Ricketts Point Marine Sanctuary.

Guest favourite
An expansive covered deck features a wooden floor, comfortable seating arrangement, and a dining area. A barbecue grill is located beside a large white fridge. Natural light filters through large windows, creating a bright and airy atmosphere, perfect for gatherings.
Apartment in Oakleigh East
4.88 out of 5 average rating, 279 reviews

Tranquil Javanese Studio and Pond!

No service/Cleaning Fees, EV Charger, Study the Antique Javanese Garden Wall or meditate by the calming fishpond. BBQ on the covered deck, also a perfect place for catching some morning rays, shared area. Settle back with a book from the well-stocked shelves. A fully self-contained Studio Apartment for two, set at the rear of a suburban block offering a comfortable, tranquil and memorable experience - you won't be disappointed! FREE Wi-Fi & off-street-Parking. LONG TERM Discounts apply.

Guest favourite
A small courtyard is illuminated with warm string lights, showcasing a wooden bench and a folding table with two chairs. Greenery surrounds the area, creating a relaxed atmosphere. The entrance features a dark gate, providing a sense of privacy.
Guesthouse in Bentleigh
4.93 out of 5 average rating, 126 reviews

Quiet, quaint and private guesthouse.

This recently renovated guesthouse is separate to the main house. • Entire guesthouse is yours • Pet friendly • Large open living area • Your own private entrance & driveway It’s private and very quiet, which makes it the perfect retreat for a family or a group of friends. Bedroom 1 has a queen bed, bedroom 2 a double bed and the living room has a large comfortable sofabed. The kitchen is fully equiped & the living room opens up to a large al fresco area - perfect for entertaining.

Top guest favourite
A spacious living area features a modern leather sectional sofa facing a circular coffee table. Natural light floods in through a skylight above, with views of the adjoining dining space and kitchen. A sliding glass door opens to a wooden deck, enhancing the open layout.
Home in Oakleigh
4.92 out of 5 average rating, 38 reviews

Brilliant Bungalow Home at Oakleigh and Chadstone

Step into a piece of history in this stunning 3-bedroom Oakleigh home. With its Art Deco charm and spacious layout, it's perfect for families looking to create a cozy and stylish living space. Enjoy the reading lounge, high-ceilinged living area, and modern kitchen. Plus, you're just steps away from Oakleigh's vibrant cafes, Chadstone shopping, and easy access to public transport. This home offers endless possibilities for customization and a truly unforgettable living experience.

Superhost
A modern living area is centered around a light grey sofa, adorned with decorative cushions featuring plant motifs. In the background, a dining table is visible, accompanied by stylish chairs. Large windows allow natural light to fill the space, enhancing the sense of openness.
Townhouse in Glen Waverley
4.88 out of 5 average rating, 252 reviews

Entire two bedrooms townhouse in Glen Waverley

Central location in glen Waverley and close with everything. A few minutes away from Brandon Park, The Glen shopping centre, Glen Waverley train station, Direct bus to Monash Uni, Monash hospital. Two Master bedrooms with own bathrooms, toilet and fully facility. Nice, quiet and comfortable. Laptop friendly workplace. Heating and cooling reverse cycle split aircon in own room. Bathroom essentials, towels, body wash, shampoo, hair dryer and much more.

Top guest favourite
The Barn presents a modern white exterior with a spacious roof, complemented by large feature doors. Gentle hills and muted clouds form the backdrop, enhancing the rural landscape. Surrounding greenery and pathways add to the welcoming ambiance of the property.
Barn in Yering
4.98 out of 5 average rating, 273 reviews

The Barn Yarra Valley

Offering panoramic views of the Yarra Valley countryside, The Barn is set on 10 acres and surrounded by the ever changing mountain landscape. This is your place to relax and unwind in the heart of the Yarra Valley. The Barn is locally known as the ideal bridal preparation space for your wedding morning and accommodation. A perfect mix of large yet homely open plan living suitable for the getting ready venue before your Yarra Valley wedding.

Superhost
A modern living area features a light gray sofa complemented by decorative cushions. A wooden coffee table sits at the center on a textured rug, while a cozy armchair is positioned beside a large window draped with sheer curtains, allowing natural light to fill the space.
Townhouse in Hughesdale
4.78 out of 5 average rating, 76 reviews

Chadstone Townhome Perfect for Family

A modern and private luxury house, perfect for a family or business traveller. Set up as a comfortable living environment with all the amenities you need for a relaxing stay here. Within the quiet and friendly neighbourhood of Hughesdale, you will have the biggest shopping centre in the Southern Hemisphere, Chadstone, located conveniently nearby. You can also reach a train station (Hughesdale) and bars/restaurants within a 5 min walk.

Guest favourite
A charming cottage is framed by vibrant autumn foliage and lush greenery. The gravel pathway leads to the inviting entrance, accented by a stone feature. The peaceful surroundings highlight the natural beauty of the property in the Dandenong Ranges.
Cottage in Sassafras
4.95 out of 5 average rating, 101 reviews

Dingleigh of Sassafras - Reader's Cottage

A forest hideaway in the Dandenong Ranges. Nestled between ferns and maples, Dingleigh of Sassafras is one of the original cottages on the property, lovingly restored and updated. Walking proximity to Sassafras, local shops, famous gardens & the national park. Dingleigh and its gardens offer an ideal location for wedding preparations and small wedding ceremonies. Photo shoots and video locations are also available upon request.

Top guest favourite
A modern living area is highlighted by a spacious, light-colored sofa and a round black coffee table. A large television is positioned on a wooden media console. Natural light fills the room through expansive glass doors that open to the outdoor space, creating a welcoming ambiance.
Home in Bentleigh East
4.9 out of 5 average rating, 99 reviews

Modern townhouse

Welcome to our newly renovated townhouse in Bentleigh East. Sleeps up to 5 guests with 2 bedrooms and a study configured as an extra bedroom. Modern interior, fully equipped kitchen, and stylish living area. Nestled in a vibrant neighborhood, just moments away from the renowned Chadstone Shopping Centre, a shopper's paradise, where you can indulge in a world of retail therapy, restaurants and entertainment options.

Popular amenities for Oakleigh vacation rentals

When is the best time to visit Oakleigh?

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Avg. price$190 CAD$175 CAD$193 CAD$151 CAD$111 CAD$130 CAD$115 CAD$99 CAD$100 CAD$115 CAD$121 CAD$158 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Oakleigh?

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

  • How much does it cost to stay in house rentals in Oakleigh?

    Experience the best of Oakleigh with our house 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.

  • Are there pet-friendly vacation rentals in Oakleigh?

    Four-legged friends are welcome in Oakleigh. Choose from more than 20 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 30 vacation rentals in Oakleigh featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Oakleigh have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Oakleigh. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oakleigh have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Oakleigh. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oakleigh have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Oakleigh. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakleigh have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Oakleigh. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Oakleigh

  • Total vacation rentals

    Explore 60 vacation rentals in Oakleigh

  • Nightly prices starting at

    Oakleigh vacation rentals start at $27 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Oakleigh vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakleigh rentals

  • 4.6 Average rating

    Oakleigh stays receive an average rating of 4.6 out of 5 from guests

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