House holiday rentals in Cheltenham

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Top-rated house rentals in Cheltenham

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Guest favourite
A spacious living area features a modern fireplace at the center, surrounded by seating options including a gray sofa and a yellow armchair. Large windows allow natural light to brighten the room, with indoor plants and a patterned rug enhancing the inviting ambiance.
Home in Belgrave
4.97 out of 5 average rating, 189 reviews

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.

Top guest favourite
A small outdoor seating area is presented with a round, mosaic-top table surrounded by two black metal chairs. The entrance is framed by a brick wall and lush greenery, with colorful flowers adding a vibrant touch near the entrance door.
Home in Aspendale
4.93 out of 5 average rating, 126 reviews

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

Top guest favourite
Home in Prahran
4.97 out of 5 average rating, 125 reviews

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.

Top guest favourite
A bright living space features a light-toned sofa adorned with cushions, complemented by a round ottoman in soft pink. A wooden TV unit holds a flat-screen television, while large windows allow natural light to fill the room, creating an inviting atmosphere.
Home in Mentone
4.97 out of 5 average rating, 76 reviews

Cosy Seaside Retreat - Charming Unit by the Beach

Discover a charming retreat just 2km from Mentone's pristine beaches. This cosy 2-storey unit boasts a fully equipped kitchen, offering a perfect blend of comfort and convenience. Immerse yourself in a relaxing getaway, surrounded by the best south-east Melbourne has to offer! Local shops, restaurants and public transportation within walking distance and a mere 35 minutes from the Melbourne CBD. This location is a great central base for anyone wanting to explore the south-east of Victoria.

Top guest favourite
An open plan living area features a spacious grey sofa adorned with colorful cushions. A striking staircase leads to the upper level, while large glass panels offer views of a lush indoor garden. Artistic wall decor and a patterned rug add character to the space.
Home in Richmond
4.96 out of 5 average rating, 102 reviews

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)

Guest favourite
A spacious living area features two comfortable leather recliners and a cozy sofa, arranged around a modern coffee table. A large wall-mounted television is positioned across from the seating, and natural light is invited through large windows, brightening the room.
Home in Highett
4.97 out of 5 average rating, 38 reviews

Highett Charm - Spacious modern 3 bedroom Unit

This 3 bedroom unit is spacious enough for a family or cosy enough for a couple. It is a short walk to the center of Highett and train station. Southland Shopping Centre is only a 3min drive away for all of your shopping needs. A spacious undercover outdoor space offers guests the opportunity to cook up a storm on the BBQ provided. Ducted heating and reverse cycle cooling for your comfort. Smart TV's are installed in all rooms. 1 undercover and one additional car space is available.

Top guest favourite
A cozy seating area features soft, circular floor cushions surrounded by natural wood accents. A modern wood stove provides warmth, while large windows allow ample natural light. A piece of artwork hangs on the wall, and a potted plant adds a touch of greenery.
Home in South Melbourne
4.98 out of 5 average rating, 160 reviews

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.

Guest favourite
A contemporary two-story house is showcased with a modern façade. Large windows allow natural light to fill the interior, and a balcony extends from the upper level. A double garage is visible on the right side, with landscaping that includes small shrubs and plants.
Home in Mentone
4.88 out of 5 average rating, 130 reviews

‘The bayside’ 6BR Beautifully brand new house

This luxury house was built in 2023 with 6 bedrooms, 4 bathrooms, spacious kitchen, private backyard and double garage. All appliances are brand new. It contains central air-condition heating & cooling. Baby friendly with chair, cot and change table. Enjoy your second home away from home. 1 minute walk to Thrift Park Shopping Centre (Woolworths, Pharmacy, Café, Restaurants, etc) 2 minutes drive to train station 3 minutes to beach STRICTLY NO PARTIES NO PETS ALLOWED NO SMOKING INDOORS

Guest favourite
The living room features a large chaise couch adorned with cushions, positioned near a fireplace. A flat-screen TV is mounted above the fireplace. Two coffee tables sit in front of the couch, complemented by a decorative plant. Natural light filters through sheer curtains.
Home in Beaumaris
4.9 out of 5 average rating, 42 reviews

Large Bayside Home

Nestled in the heart of Beaumaris, this spacious 3-bedroom, 2-bathroom home is ideal for both short and long-term stays. Situated on a peaceful street with off-street parking, discounts of 10% are available for stays of 1 month or more. Conveniently close to shops, cafes, and bus stops, the home is just a short walk from Beaumaris Secondary College. It’s also within the coveted Mentone Girls’ Secondary College zone, top-rated primary schools, and only minutes from the bay.

Top guest favourite
Home in Mordialloc
4.95 out of 5 average rating, 21 reviews

Mordi Beach House Getaway

Enjoy the crisp sea breeze and sunshine in our bright, contemporary beach house. It’s your perfect blend of relaxation and style. • Open-plan living • Spacious bedrooms with plush bedding • Outdoor living&BBQ equipment • Fully equipped kitchen • Onsite restaurant Whether you’re here for a romantic escape, a family holiday, or a weekend with friends, our beach house offers the perfect mix of relaxation and indulgence. Enjoy morning walks by the creek and sea.

Top guest favourite
An outdoor area is visible, featuring a charming archway and a brick pathway. The bright facade of the house is adorned with large windows, allowing natural light to illuminate the space. Potted plants and flowers add vibrancy, while a chicken strolls leisurely.
Home in Belgrave
4.96 out of 5 average rating, 134 reviews

The Gables 2

The Gables is a gracious old house on three beautiful acres in Belgrave, close to wedding venues, national park, Trees adventure and Puffing Billy. We do not allow events at all, but we have many brides who stay with their bridesmaids on the eve of their wedding and have beautiful pre-wedding photos taken here. We are limited in parking to only 5 cars. There is a bathroom for each double room. Please be aware that we live on the property in the cottage next door.

Top guest favourite
A bright bedroom is presented with a spacious bed covered in a soft, neutral-colored blanket. Two bedside lamps illuminate the space, and wall-mounted artwork complements the natural light from the large window. Built-in wardrobes and a shelf with books enhance the room's functionality.
Home in Elsternwick
4.99 out of 5 average rating, 119 reviews

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.

Popular amenities for house rentals in Cheltenham

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Quick stats about house rentals in Cheltenham

  • Total holiday rentals

    Explore 60 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 610 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Cheltenham holiday rentals include wifi 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!

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