
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.

Tranquil hideaway - escape to the rainforest
Welcome to Steep Creek Retreat, a peaceful oasis. You'll be treated to a warm and comfortable 3 bedroom house nestled in the rainforest, with views of Belgrave Lake Park, trees and ferns, possums, birds and the most wonderful forest sights and sounds. Feed rainbow lorikeets on the verandah, sit by the fire, relax in the bath, scramble down to the park and Monbulk Creek walks, or stroll to Puffing Billy or Belgrave's bands, bars and night life. When you're here, it feels like another world.

Richmond Hill’s best ‘Home Hotel’ with City Views
Start the day in this architecturally designed haven with a cup of coffee on a peaceful deck under a shady tree. Cook on a Smeg gas stove in a stylish kitchen and freshen up in a crisp white bathroom. When the day is done, discover a living room and loft bedroom with a view of the city lights & stars above. The house is on the famous Richmond Hill & it's within walking distance to many restaurants, cafes, sporting venues inc. the MCG and Tennis Centre, parks and gardens, as well as the CBD.

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.

Sophisticated art deco in the heart of Toorak
Welcome to our stylish contemporary home located in the most exclusive and peaceful sanctuary within THE prestigious suburb Toorak in Melbourne, that you will have all to yourself. Strolling distance from both bustling central locations Toorak and Hawksburn Villages that are filled with fabulous local restaurants and chic boutiques. 5 mins walking distance from public transport and 5 mins driving distance from major highways, it is the most perfect getaway place for your visit in Melbourne.

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)

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.

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.

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

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.

Mountain Ash
Welcome to Mountain Ash! Wrapped with a bank of windows with forest views and elevated cathedral ceilings, a full sized kitchen and a real wood fire, this space is suited for couples and families alike. Settle in and enjoy a wine or hot chocolate by the fireplace, or lose yourself amongst the natural forest surrounds, with plenty of shops and hiking spots nearby.
Popular amenities for house rentals in Oakleigh
House rentals with a pool

4 Bedroom Home in the foot of Yarra Ranges

OG Camberwell 5-BR Escape Pool Alfresco Nights

Toorak Luxury Living

4 Bedroom Home with Pool Aircon WIFI

Yarra Valley Serenity House in Golf Country Club

Camellia Waterfall Mountain View Retreat

Tanglewood

Oliver's Cottage Yarra Valley | Spa and Sauna
Weekly house rentals

Melbourne - Elegant Victorian Terrace - Parking

The Black Cockatoo

Bushland Getaway

Material Girl • Artist-curated terrace off High St

Elegant Caulfield North Family Home

The Dunes I Step Onto Sand I CBD & Peninsula

Murrumbeena delight.

House of Windsor
Private house rentals

Delux 4 Bedroom 3.5 Bathroom Camberwell Townhouse

Glen Waverley 4BRM house in Court near Jells Park

Glorius Aspendale beach house

Sebastopol House - 2 Bedroom Pet Friendly Oasis

George on George

Rustic older home in a vibrant seaside village

Holly Hill Cottage

Luxury Mountain Retreat in the Dandenong Ranges
When is the best time to visit Oakleigh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $150 SGD | $160 SGD | $154 SGD | $200 SGD | $178 SGD | $172 SGD | $108 SGD | $113 SGD | $134 SGD | $151 SGD | $173 SGD | $168 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





