
House holiday rentals in Oakleigh
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Top-rated house rentals in Oakleigh
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Jacky Winter Gardens - Modern, Artistic Cabin Close to Creek
Recharge by the open fireplace of this beautiful cabin, sequestered in the Dandenong Ranges. Rustic on the outside, modern on the inside, this serene space inspires relaxation in proximity to wild nature, far from the stresses of daily life. Designed by interior architects Hearth Studio, Jacky Winter Gardens brings together the calming waters of Clematis Creek, the rich soil of the gardens, the pure air of the Dandenong Ranges and every modern convenience you can imagine to give you a wholly satisfying holiday experience. Our mission is to offer private and secluded luxury accommodation for visitors to the hills, including singles, couples and small groups, as well as showcase the work of our artists and incorporate it into the day-to-day life of the house. Through our monthly artist-in-residence program we also support other commercial artists working in any discipline. We’ve feathered our nest with work from some of The Jacky Winter Group’s world-renowned stable of artists. From custom-made glasswork and wallpaper, to games and framed prints, you’ll become acquainted with new artists, or perhaps be reunited with some you already know. The beautiful Clematis Creek meanders along the bottom of the gardens, and its cheerful burbling is the aural backdrop to your stay. If you want to get closer to the water there is easy and safe access down to the creekbank, which makes it the ideal spot for meditation or private reflection. Located just 45-minutes from Melbourne by car, and situated within walking distance to the town centre with its wonderful Cameo Cinemas, Jacky Winter Gardens straddles the two worlds of nature and civilisation, achieving a perfect holiday balance for solo travellers, couples and small groups. You can find more information and photos of the property online at our dedicated property site which isn't difficult to find ;) During their stay, guests have private and exclusive access to the entire house, gardens, and studio. None, but available on phone, email, and in person (when possible) to answer any questions! The house is a luxury creative retreat set amidst a half-acre of stunning flora, a creek, and natural bushland. The wild yet tranquil beauty of the Dandenong Ranges has attracted artists to the area for more than a century. Jacky Winter Gardens is situated in Belgrave, Victoria, a short walk from the train station and centre of town. Full directions will be provided upon booking. Car – Belgrave is a 45-minute drive from Melbourne. Train – From Flinders Street Station, catch the Belgrave train to Belgrave Station (it takes just over an hour). Jacky Winter Gardens is a ten-minute walk along a paved walkway from the train station. Jacky Winter Gardens is the perfect retreat for solo travellers or couples, but we are able to accommodate up to five guests: two in the master bedroom, two in the living room on the double-bed fold-out sofa, and one in the studio on a single sofa bed. Jacky Winter Gardens is now dog and child friendly. We also accept single night bookings when available. ***Please message us if you wish to bring your pet or want to stay for a single night before booking*** Each additional guest (beyond the first two) will incur a tariff of 25.00 per night. Unfortunately, due to site limitations, there is no wheelchair access at this time. Due to our location in a high fire risk area, we also have detailed Fire Safety policies which are outlined on our website, which once again is not hard to find.

Maple Cottage - Charming Home With Fireplace
Welcome to our sweet home nestled amongst the quiet leafy streets of Blackburn. A charming and inviting space to unwind with a warm cuppa or a glass of something special. Enjoy its character and spend your days relaxing by the fire or overlooking the garden, or visit Blackburn Lake, the local cafes, or the Yarra Valley wine region. And you’re only a short train ride away from Melbourne city! And once you finish your adventures, Maple Cottage is the perfect cosy place you’ll love to come home to.

Entire house + parking near MCG, city, everything
Homely, peaceful, private, spacious Victorian heritage cottage with your own secluded garden and carport, in a quiet neighbourhood conveniently close to everything Melbourne has to offer. Simply walk or tram/train/uber in minutes to the city centre, MCG, live music venues, theatres, galleries, gardens, parks and bayside beaches. Perfect work-from-home hub, and base for drives to regional and coastal Victoria. For an inner city Melbourne stay that is not an apartment or hotel look no further.

Quiet Designer Home steps from High St & Hawksburn
Woodfull House is a an immaculate, luxury three bedroom house located in peaceful street and ideally situated on the green fringe between the happening Prahran/South Yarra precinct and Toorak/Armadale. Enjoy morning coffee in the private designer garden, cook in the fully equipped kitchen, and relax by the fireplace after exploring Melbourne. Unlike some inner-city stays, natural light fills every room. Generous living spaces and outdoor garden — ideal for families, friends or longer stays.

Sherlock's Home - Magical Richmond Warehouse
Sherlock’s Home, a one-of-a-kind 1850s Cordial Factory warehouse conversion in the best part of Richmond (as featured on Broadsheet). Architecturally-designed to maximise openness, our bespoke house is over 4 levels, with 2 bedrooms (Master with king bed & ensuite), 2 lounge areas, single garage, & shaded northern patio. Our exclusive Melbourne location is unbeatable: - 100m to Church St - 200m to Bridge Rd - 750m to Swan St - 1.9km to Sports Precinct (MCG, Rod Laver Arena, AAMI Park)

Arranmore - a charismatic Terrace House
+ 5-7 mins walk to trams & buses + Tram 48 to the city stops at the MCG + 10 min walk to Tram 16 to St Kilda Beach + 5 min walk to closest supermarket + 5 min walk to High Street filled with cafes, restaurants, grocers, bakeries, retail and bottle shops + Visit Lyon Housemuseum + Visit Yarra Bend, Melbourne's largest natural bushland reserve, Yarra River & Dights Falls + Visit Studley Park Boathouse for dining or boat hire + Local golf courses + Close to Fitzroy, Collingwood and Carlton

Beautifully curated 2 bedroom home
This 100 year old workers cottage is all about bespoke interiors The walls and shelves filled with gorgeous art work, the home has specially sourced vintage pieces scattered everywhere, the beds are filled with luxurious linens and the lounge has a 3 seater couch you may never want to get up from. Centrally located, across the road from the South Melbourne Markets, walking distance to the Albert Park Lake and a quick tram trip to the CBD. Please note- no TV, so bring devices if needed.

Edwardian charm, Resort living
Four Bedroom, huge living areas combine with superb landscaped garden including pool and putting green. Close to Brighton beaches, and easy walking to public transport and shops. A perfect location to explore Melbourne's famous sand belt golf courses .pet friendly, welcome hamper.everything supplied.10 minute walk to rail and tram, 20 minute trip to CBD melbourne. surrounded by parks and golf courses.unlimited internet and cable tv with surround sound .all rooms heating and aircon.

Yarra Valley Gateway Stay
On the doorstep to the Yarra Valley Wine region, this is a private home, vacated for your stay so you have the entire property to yourself. It is set on 1 acre in a quiet court and is popular with wedding & festival guests, family & pets stays, wine buffs and yarra valley explorers. Set atop a hill that offers the serenity of generous Yarra Valley views, the home is appointed to entertain. Pets are welcome including access to stables and electrobraid paddock.

Charming Victorian Getaway with Outside Images
This beautifully renovated Victorian terrace is bright clean and welcoming with all the modern comforts. It is in the heart of Elsternwick in a quiet tree lined street. Only a 1-2 minute walk to Cafe’s , restaurants and shops. Public Transport is very close with the tram about a 2 minute walk or the train an 8 minute walk. By train you will be in the city centre in 16 minutes. Two $12 Myki(public transport cards) are also provided for your use.

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.

Precinct Cottage (Olinda - Old Police station)
Stay in the heart of Olinda Village at the Old (heritage) Olinda Police Station. From the moment you step into the Cottage grounds you are surrounded by history and the sights and sounds of nature. All local attractions are only moments away. You can retreat to the cottage to enjoy the luxury accommodation and facilities, experience the local village or explore the great surroundings on your door step.
Popular amenities for Oakleigh house rentals
House rentals with a pool

4 Bedroom Home in the foot of Yarra Ranges

Toorak Luxury Living

4 Bedroom Home with Pool Aircon WIFI

Hanging Garden-Mountain Views Retreat

Family Cityside Beach House, Pool & Roof Terrace

Yarra Valley Serenity House in Golf Country Club

Tanglewood

Molly’s Modernist Bayside Beach House
Weekly house rentals

Bush House in the Dandenong Ranges

A Sylvia Home in Deepdene

Material Girl • Artist-curated terrace off High St

Murrumbeena delight.

Bentleigh Private 1BR 5min Train Cafes Quiet Cozy

Close glenhuntly train station one bedroom unit

Gerty Longroom: Rooftop onsen & fresh produce

Country Style 2 bedroom House - Off Street Parking
Private house rentals

Melbourne - Elegant Victorian Terrace - Parking

Glen Waverley 4BRM house in Court near Jells Park

Bushland Getaway

Glorius Aspendale beach house

Home of Susan Close

Yarra Valley -Yerindah luxe couples retreat.

Albert Park Loft & Luxury

George on George
When is the best time to visit Oakleigh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $201 NZD | $215 NZD | $206 NZD | $267 NZD | $238 NZD | $230 NZD | $145 NZD | $152 NZD | $179 NZD | $203 NZD | $232 NZD | $225 NZD |
| Avg. temp | 20°C | 20°C | 19°C | 15°C | 13°C | 11°C | 10°C | 11°C | 13°C | 14°C | 17°C | 18°C |
Quick stats about house rentals in Oakleigh

Total holiday rentals
Explore 20 holiday rentals in Oakleigh

Nightly prices starting at
Oakleigh holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 160 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Oakleigh holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oakleigh rentals

4.8 Average rating
Oakleigh stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Melbourne Holiday rentals
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- West Melbourne Holiday rentals
- Brunswick Street
- Phillip Island
- Melbourne Central
- Crown Melbourne
- Melbourne Convention and Exhibition Centre
- Marvel Stadium
- St Kilda beach
- Rod Laver Arena
- Peninsula Hot Springs
- Sorrento Beach
- Melbourne Cricket Ground
- Queen Victoria Market
- Smiths Beach
- Sorrento Back Beach
- Puffing Billy Railway
- Melbourne City Centre
- Geelong Waterfront
- Royal Botanic Gardens Victoria
- West Side Place
- AAMI Park
- Flemington Racecourse
- Melbourne Zoo
- Mount Martha Beach North
- Somers Beach





