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

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.

Bayside getaway, Impressive 1 bedroom apartment!
Comfortable apartment in Bayside Highett, a 2 min walk to train/bus stops, restaurants, bars & shops, 3 mins to major shopping centre, 10 mins to the beach & 30 mins to the city, conveniently positioned to explore Melbourne! Perfectly setup for couples & solo adventurers. As this is a whole apartment you have a fully equipped kitchen, private courtyard, laundry facilities and Netflix to be able to enjoy your stay. 24 hour check in with a key safe. Garage parking for small to medium sized car.

Beachside retreat
This 3-bedroom family home is perfectly located in the bayside suburb of Aspendale, Melbourne. Short walk to Aspendale Beach, and Mordialloc Pier, you will enjoy the ocean and the white sands of the bay and the local shopping district. As it is a quiet neighborhood, we have a no-party policy. Three bedroom, 2 queen & 1 trundle Off-road carport Free Wifi, Netflix, Microwave, Fridge, Stove and oven, Dishwasher Cookware and Dinnerware Pillows, Quilts, blankets Modern Laundry Private backyard

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.

Bayside Bungalow
Backing onto the Victoria Golf Club, this stand alone bungalow is highly accessible to Victoria, Royal Melbourne, Sandringham and Cheltenham Golf clubs. It's a 10 minute walk to Cheltenham train station, close to shopping strips and a 5 minute drive to Southland Shopping Centre. It's modern, private, with Japanese screens allowing for natural light and block out blinds for full privacy. It is comfortable in a beautiful backyard setting with, its own access and a 3-minute drive to the beach.

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.

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

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

Black Rock Beach Escape - Pool, Beach, & Village!
A treasure in a fantastic location with great facilities - close to everything! This is an open plan unit with a seperate bathroom and a fully appointed kitchen that faces the pool and outdoor area. Seperated from the main house with private access and just 300m from the lovely Black Rock beach and 500m to black rock village restaurants, bars, and cafes. The coastal bike path provides over 30km's of safe cycling, and beautiful walks along the coastline tracks.

Spacious and cozy 3 bedroom home
Welcome to our spacious and cozy family home with WiFi. Easy access to transportation and neighbourhood. There are many fantastic cafes, restaurants, fast food, bakeries around. Plus! There are many supermarkets and shopping centres like DFO, Costco, Westfield Southland are all within a few minutes drive away. The nearest beach is about a 4-minute drive. Ideal for holidays, business trips, and families for long and short term temporary stays.

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.
Popular amenities for Cheltenham family-friendly rentals
Family-friendly home rentals with a hot tub

Wild Orchid Olinda ~ Luxurious Private Cottage

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

Tranquil Estate | Pool, Hot Tub & Gardens

Stylish Central Terrace with Natural Wood Fire

Olinda Woods Retreat

GreyGum Getaway fully renovated home in the forest

Villa with Lush Gardens, Spa & Fireplace

Merri Loft
Family- and pet-friendly home rentals

St Kilda/Elwood water views - Woy Woy Two

The Chambers - South Yarra Luxury and Location

Modern Studio with a View in Selby-Belgrave

King bed,Ideal for long /short term stays Richmond

Tanglewood Cottage Wonga Park

Quiet Designer Home steps from High St & Hawksburn

Newly Renovated 2 Bedrooms Bentleigh Retreat

"Yering Park Cottage"
Family-friendly home rentals with a pool

Port Melbourne Perfect 2 Bed

Stylish Stay - 2 kms to Westfield Shoppingtown
///ARCHITECTURAL HOME / BEACH /CBD / CAFE PRECINCT

Port Melbourne Beachsider Princes Pier

Tranquil retreat and apartment in Mount Eliza.

Luxury Accommodation with rooftop Pool.

Loggia in Leafy Camberwell, Australia

Tammex Luxury Properties - Melbourne Square
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $183 AUD | $174 AUD | $183 AUD | $157 AUD | $151 AUD | $149 AUD | $162 AUD | $156 AUD | $165 AUD | $167 AUD | $175 AUD | $242 AUD |
| 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 Cheltenham

Total holiday rentals
Explore 70 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 1,350 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Cheltenham holiday rentals include Wi-Fi access

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

4.8 Average rating
Cheltenham stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Family-friendly rentals Victoria
- Family-friendly rentals Australia
- 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
- Torquay Beach
- Geelong Waterfront
- Melbourne City Centre
- Royal Botanic Gardens Victoria
- AAMI Park
- Flemington Racecourse
- Mount Martha Beach North
- West Richmond Station
- Somers Beach





