
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.

Space design luxury. Zinc house - urban oasis
Private and spacious ultra modern 2 Storey townhouse, minutes walk from the Windsor restaurants and cafes in Chapel Street. Relax on the big red couches surrounded by the art and music. Fully equipped kitchen. Classic Victorian dining table. Bedrooms boasting space, big comfy mattresses, quality linen, and fluffy doonas. Private courtyard. Easy parking. Easy access. Perfect living. Your host is the owner. Whether for pleasure, business or visiting friends the ultimate Windsor abode.

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)

"Yering Park Cottage"
"Yering Park Cottage" is set in a private garden setting on 1/2 acre of landscaped gardens with beautiful rural and mountain views at the gateway to the Yarra Valley, only minutes from Coombe-The Melba Estate, Stones, Meletos, Yering Station, wineries and other attractions such as world class golf courses, restaurants, Healesville Sanctuary and township. Fully renovated offering excellent accommodation for up to 6 guests, large living/kitchen/dining area, separate toilet and laundry

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.

The Chambers - South Yarra Luxury and Location
The Chambers has everything you'll need for a luxurious Melbourne getaway. Up to 9 guests may revel in the spacious comfort and convenience of the 3 bedrooms and 3 bathrooms. We are located less than a hundred meters from the best cafes, restaurants, art galleries and shopping of Chapel St and Toorak Rd. Prahran Market, Artists Lane, Como House & Garden, and Royal Botanic Gardens are nearby attractions. Furthermore, South Yarra Station and numerous trams are less than a 5 min walk.

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.

Inviting light filled home with cozy fireplace
Welcome to Casa on Clyde, our beautiful 1870's period home in the heart of St Kilda. Enjoy the light filled spaces, sitting in front of the cosy fireplace or star gazing via the skylights whilst lying in bed. Walking distance to cafes, restaurants, theatres, nightlife, Sunday markets, beaches and all the other eclectic attractions St Kilda is famous for. Trams are located at the end of the street for easy access into any other pocket of Melbourne.

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.

Position Perfect! In the heart of Sherbrooke
Less than an hours drive from Melbourne CBD, situated in heart of Sherbrooke, this Eco accommodation is perfect for your next weekend or mid week get away. We are located just a short stroll to Burnham Beeches, Alfred Nicolas Gardens, Poets Lane, Woods Cafe, Marybrook Manor and Sherbrooke Falls. Perfect for two couples, this immaculate light and spacious fully self contained recently renovated 2 bedroom home.

No.63 on Brunswick St Fitzroy
The city is on your doorstep. Steps away from Gertrude St, a 10 minute walk from Smith St and a 15 minute walk to the MCG. Located above a design studio the space is curated for an exceptional stay. A modern take on heritage interiors. The large living & dining has a kitchen with cooking facilities. Large comfortable bedrooms face towards the rear of the property A courtyard has dining furniture
Popular amenities for house rentals in Oakleigh
House rentals with a pool

4 Bedroom Home in the foot of Yarra Ranges

Lumiere - Gas Heated Pool & Stroll to Beach

4 Bedroom Home with Pool Aircon WIFI

Location, BBQ, roomy and privacy

Yarra Valley Serenity House in Golf Country Club

Tanglewood

Molly’s Modernist Bayside Beach House

Luxury Seaside Estate with Pool & Garden Oasis
Weekly house rentals

Melbourne - Elegant Victorian Terrace - Parking

The Black Cockatoo

Bushland Getaway

Murrumbeena delight.

Close glenhuntly train station one bedroom unit

House of Windsor

Gerty Longroom: Rooftop onsen & fresh produce

Private cottage in 1/2acre forest Dandenong Ranges
Private house rentals

Delux 4 Bedroom 3.5 Bathroom Camberwell Townhouse

Prahran Perfection

Glen Waverley 4BRM house in Court near Jells Park

Material Girl: Artist-curated terrace off High St

Elegant Caulfield North Family Home

The Beach House: Waterfront with Boat Mooring

May & June SALE! 3 Bedrooms+ Parking Amazing Price

Tido Art Haven @ Mt Waverley Ⅱ
When is the best time to visit Oakleigh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 SGD | $160 SGD | $153 SGD | $199 SGD | $177 SGD | $171 SGD | $108 SGD | $113 SGD | $133 SGD | $151 SGD | $172 SGD | $167 SGD |
| 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 $25 SGD 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 & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oakleigh holiday rentals include wifi 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
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- Brunswick Street
- Phillip Island
- Melbourne Central
- Crown Melbourne
- Melbourne Convention and Exhibition Centre
- Marvel Stadium
- St Kilda beach
- Rod Laver Arena
- Sorrento Beach
- Peninsula Hot Springs
- Melbourne Cricket Ground
- Queen Victoria Market
- Smiths Beach
- Sorrento Back Beach
- Puffing Billy Railway
- Geelong Waterfront
- Melbourne City Centre
- Royal Botanic Gardens Victoria
- AAMI Park
- Flemington Racecourse
- Mount Martha Beach North
- West Side Place
- West Richmond Station
- Palais Theatre





