Vacation rentals in Cheltenham

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Top-rated vacation rentals in Cheltenham

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
Guesthouse in Sandringham
4.98 out of 5 average rating, 177 reviews

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.

Top guest favourite
A spacious bed is situated beside a stylish nightstand, featuring a decorative lamp and a vase of fresh orange roses. A soft throw is draped over the bed, complementing the light-colored bedding and brightening the serene bedroom atmosphere.
Apartment in Highett
4.92 out of 5 average rating, 142 reviews

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.

Superhost
A cozy interior features a spacious bed dressed in neutral tones, positioned next to a window displaying natural light. An adjoining kitchenette, equipped with modern appliances, is complemented by wooden accents. A comfortable seating area adds to the inviting atmosphere, accentuated by warm wooden flooring and soft lighting.
Guesthouse in Cheltenham
4.88 out of 5 average rating, 24 reviews

The Sanctuary Healing Retreat

Experience a luxury tranquil oasis designed for rejuvenation amidst nature. Unwind in top of the range Clearlight Sauna, refresh with an alfresco shower, and indulge in an open-air bath with magnesium and essential oils. Low EMF/TOX building biology build. Luxury Creswick bed. Alpaca doona and blanket. No smoking/vaping on property. Bus that goes to train station and Southland shopping centre or a 15 minute walk. 800m from IGA/chemist/post office. 7 minutes drive to Sandringham Beach.

Top guest favourite
A warmly decorated living space features a mix of vintage furnishings, including a green armchair and a vibrant dining table. Bright wall art adds character, while rich wooden accents and original floorboards create a cozy ambiance. Natural light streams in through the adjoining corridor.
Condo in Beaumaris
5 out of 5 average rating, 102 reviews

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.

Guest favourite
A modern bungalow is depicted with large sliding doors that open to a spacious outdoor area. A wooden dining table surrounded by chairs is visible on the patio, while the lush green lawn enhances the serene setting. Natural foliage lines the perimeter, providing privacy.
Guesthouse in Cheltenham
4.88 out of 5 average rating, 457 reviews

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.

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
4.97 out of 5 average rating, 157 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 modern living space is featured, showcasing a neutral-toned sofa and a coffee table adorned with decor. A dining area with a wooden table and upholstered chairs is visible, while a well-equipped kitchen with light cabinetry and appliances is in the background. Sheer curtains allow soft light to fill the room.
Home in Highett
4.92 out of 5 average rating, 13 reviews

Bayside Retreat: Beach & Dining

Enjoy a newly renovated home just 5 minutes from Melbourne’s best beaches—Black Rock, Sandringham & Beaumaris. This stylish, spacious house features brand-new amenities, and a large, fenced garden. Also close to golf courses, train station, restaurants, cafes, supermarkets, Westfield Southland Shopping Centre, and a renowned bakery at the end of the street - it offers the perfect mix of comfort, style & convenience for your Bayside getaway. Open to longer term bookings!

Home in Cheltenham
4.5 out of 5 average rating, 14 reviews

Cozy unit close to golf & shops

Golf, Beach, Eat, & Shop. Freshly renovated, this property offers it all — wake up to birdsong and leafy views from Cheltenham Reserve, then stroll to bustling Charman Road for coffee, shopping, bit of golf, and great local eats, or leave the car and take train into the city for a night out. Or simply relax in the private courtyard. You can do it all here. 2 bedrooms, child friendly, secluded and private, perfect for couples, small families, work or golfing getaways!

Superhost
A well-appointed bedroom contains a spacious bed with decorative pillows and a cozy throw. Nightstands with lamps are located on either side. A small desk and chair are visible in the background, accompanied by framed wall art. Natural light enters through a window with minimal coverings.
Apartment in Sandringham
4.84 out of 5 average rating, 109 reviews

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

Top guest favourite
A calm outdoor area features a sparkling pool bordered by large tiles. A spacious lounge area is shaded by an umbrella, with cushioned seating and potted plants providing a relaxing atmosphere. The backdrop includes a modern structure with sliding doors that offer access to the interior.
Guesthouse in Black Rock
4.96 out of 5 average rating, 178 reviews

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.

Top guest favourite
The Barn presents a modern white exterior with a spacious roof, complemented by large feature doors. Gentle hills and muted clouds form the backdrop, enhancing the rural landscape. Surrounding greenery and pathways add to the welcoming ambiance of the property.
Barn in Epping
4.98 out of 5 average rating, 270 reviews

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.

Top guest favourite
The outdoor pool area showcases a spacious, inviting swimming pool surrounded by hardwood decking. Two loungers with striped cushions are positioned under an umbrella for shade, while lush greenery borders the space, providing privacy and a serene atmosphere.
Home in Sandringham
5 out of 5 average rating, 18 reviews

Molly’s Modernist Bayside Beach House

Single level brick 1970's house with a fabulous swimming pool. 3 bedrooms, 2 bathrooms, outdoor dining, 2 living rooms, separate dining and spacious kitchen. Featuring beautiful archways, quarry tiles, Japanese square bath and solid Modernist charm. The home is 400m to the beach, 1km to local village and train station. **Please note - you need at least 1 air bnb reference from past stays for your booking to be accepted**

Popular amenities for Cheltenham vacation rentals

When is the best time to visit Cheltenham?

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Frequently Asked Questions

  • How much does it cost to stay in serviced apartment rentals in Cheltenham?

    Experience the best of Cheltenham with our serviced apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Cheltenham?

    Yes! Work meets play with ease at over 30 house rentals in Cheltenham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Cheltenham?

    Four-legged friends are welcome in Cheltenham. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there Cheltenham vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Cheltenham, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Cheltenham have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheltenham have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do serviced apartment rentals in Cheltenham have wifi?

    Absolutely! We offer over 10 serviced apartment rentals with wifi in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Cheltenham have free parking?

    Absolutely! We offer over 30 apartment rentals with free parking in Cheltenham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Cheltenham?

    Cheltenham has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Cheltenham?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with a kitchen, over 40 homes with air conditioning, over 30 homes with wifi, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Cheltenham

  • Total vacation rentals

    Explore 150 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    130 of Cheltenham vacation 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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