
Family-friendly holiday rentals in Oakleigh
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Top-rated family-friendly 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.

Vintage Caravan, Rainforest & Lyrebirds
Our 1959-vintage caravan is just 12ft long, best for a couple or two friends. At a pinch, two children could sleep in the king single bed; see the photos and description further down. Wake up to the sounds of Lyrebirds, enjoy a private walk in our rainforest gully and stroll around the garden, one of the best private gardens in the Dandenongs. Offering a minimum one-night stay for a quick getaway, or stay longer & enjoy the peace, sit by the fire - made from a beer keg, and roast marshmallows.

Delightful self contained cottage
The cottage is self contained and is a well designed space that accommodates a queen sized bed, bathroom and a separate study and is set in an enchanting cottage garden. The well equipped kitchen is in a separate space though part of the cottage and is accessed by its own door from the decking, so you don't have far to go. In the morning lorikeets and other wild birds come to feed and you will be awoken to the romantic sound of birdsong. During spring and summer the garden is at its loveliest.

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.

Loggia in Leafy Camberwell, Australia
The Loggia is a standalone bungalow with Queen-sized bedroom; en-suite bathroom; combined kitchen/living room, large flat-screen TV. Private access via driveway. Walking distance to Train / Tram. - Approximately 30 mins to MCG / CBD via Train. - About an hour via Tram as stops every few blocks. Safe parking on quiet leafy street. Great Cafes/Restaurants within easy walking distance. Booking includes provision of initial breakfast supplies, shampoo/conditioner; hairdryer; iron/board, etc.

Private check in, studio+ensuite. Walk to train
Private entrance - come and go as you please! Elsternwick location: - 🏬 600m walk: Gardenvale 🚂 Station, cafes, stores, laundromat - 🚂 18 min to Flinders St Station - 🚌 30 min to Monash University - 🚘 Car Rental (5 min walk) - 🏖 2.5km to Elwood Beach, 3 rail stops to Brighton Beach Amenities: 🛌 1 xQueen sized bed 🛀 Private bathroom with rain-shower 💻 Desk & unlimited Wifi 🏊 Access to heated pool in summer. ☕️ Kettle, mugs, coffee & tea making facilities, (no kitchen nor laundry)

Studio 1156
This apartment has been recently renovated in 2021. Located on high street, renowned for fashion, galleries and antique shops and public transport. The apartment is sleek, liveable and maintains total privacy. It is the ideal blend of design and comfort. Perched up looking over high street and the village, this open-plan light filled space is equipped with a hand crafted kitchen, a cosy fireplace and a walk in shower bathroom. Triple glazed windows, sound proof from high street traffic.

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.

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.

House of Friends in Kangaroo Ground
This private country retreat residence on a shared 25 acre hobby farm located within the Dress circle of Kangaroo Ground. Beautiful city views suround the home, kangaroos pay a visit most early mornings. Our paddocks are homes to horses, our roads welcome bike riders. The Beautiful Fondatas restaurant is only 2kms away, only 40 minutes from Melbourne CBD at the gateway to the Yarra Valley & it’s magnificent wineries, this farm home offers something for everyone. @casa.diamici on insta

Urban Retreat Spacious & Secluded Parklands Oasis
Located just metres from Darebin Parklands, this immaculately presented spacious unit is within walking distance of the Ivanhoe shopping strip. Darebin and Ivanhoe Stations are just a couple of minutes walk away making trips to the city and beyond a breeze. Our property has a newly renovated kitchen/ dining/ living space and bathroom/ laundry and is fully furnished with everything you need for a comfortable stay. The bedroom opens to a sunroom overlooking the beautiful parklands.

One Bedroom Premium Apartment
One Bedroom Premium Apartments include: - One spacious bedroom with King/Queen sized bed - Bathroom with shower & hairdryer - Fully equipped kitchen facilities - Open plan living and dining with 50” Crystal LED UHD 4K Smart TV - Private Laundry equipped with iron & ironing board - Private balcony with outdoor furniture - Individually controlled ducted heating and air conditioning - Bluetooth clock/radio - Direct dial telephone - Complimentary high speed Wifi Internet
Popular amenities for Oakleigh family-friendly rentals
Family-friendly home rentals with a hot tub

Beach Living - “A bit of Mykonos near Mordialloc!”

Luxury Home with a spectacular view

The Luxe Loft - Melbourne Square

Olinda Woods Retreat

Mountain View Spa Cottage

Left Yarra Valley Barrel Sauna & Spa - Urban List

Spacious and cozy 3 bedroom home

Neat&Clean 1BR Apt w/Pool, Gym, CarPark, Free Tram
Family- and pet-friendly home rentals

Quiet, quaint and private guesthouse.

Modern Studio with a View in Selby-Belgrave

Inner City Cottage - Stylish - Amazing Location

20% Off: Spacious & Cozy Holiday tiny house

Henry Sugar Accommodation

King bed,Ideal for long /short term stays Richmond

Quiet Designer Home steps from High St & Hawksburn

Art Deco Gem Entire 2BR Quiet⭐Wifi⭐Netflix⭐Parking
Family-friendly home rentals with a pool

Close to Melbourne CBD, Studio with pool & parking

Stylish Apartment, Resort Facilities and Location!

Delux 2B with Balcony/Pool/Sauna/Gym walk to Crown

St Kilda stunner - rooftop infinity pool + parking

Black Rock Beach Escape - Pool, Beach, & Village!

Modern Clean 1 BR near Monash (2)

Cityscape Haven 2B2B with Stunning City Views

Modern 2BR Resort-style living
When is the best time to visit Oakleigh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $218 SGD | $192 SGD | $222 SGD | $205 SGD | $183 SGD | $206 SGD | $208 SGD | $202 SGD | $209 SGD | $229 SGD | $228 SGD | $273 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 holiday rentals that are family-friendly in Oakleigh

Total holiday rentals
Explore 20 holiday rentals in Oakleigh

Nightly prices starting at
Oakleigh holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 430 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

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

4.7 Average rating
Oakleigh stays receive an average rating of 4.7 out of 5 from guests
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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
- University of Melbourne
- Peninsula Hot Springs
- Melbourne Cricket Ground
- Queen Victoria Market
- Sorrento Back Beach
- Redwood Forest
- Puffing Billy Railway
- Geelong Waterfront
- AAMI Park
- Royal Botanic Gardens Victoria
- Mount Martha Beach North
- Flemington Racecourse
- West Richmond Station
- Palais Theatre
- Point Nepean National Park




