Holiday rentals in Woollahra

King or 2 single beds-own bathroom- Bondi Junction

The perfect private hotel-style room conveniently located in the heart of Bondi Junction. Recently renovated, our cosy guest room has a private entrance, bathroom, small kitchenette and a share outdoor space. Set up as 1 king or 2 single beds and has access to free parking and laundry. Located on the fringe of Woollahra, 2mins to Bondi Junction station with easy access everywhere, 1min to Westfields, 10mins to the city, 30mins to the airport and a short bus ride or 20min walk to Bondi Beach.

Little Edie charming architect designed cottage

A gorgeous, free-standing two level stables converted into a chic, fully self contained cottage in the heart of Paddington's leafy streets, Little Edie is an architecturally designed jewel box for grown ups providing the perfect place to rest and relax during your next visit to Sydney. Centrally located, it is two blocks from Oxford Street's boutiques, bars, restaurants, public transport and just a few minutes from the city, sports stadiums and glorious beaches. We love giving local tips too!

Whimsical Woollahra short/long term

Elegant garden apartment in a coveted Victorian boutique block. Boasting high ceilings and spacious rooms flowing out to two outdoor entertaining areas. The grand study/office room has a day bed for an extra guest. Two generous living spaces. Ideal for the discerning guest. Plus Laundry Room. Walk to the vibrant cafes, restaurants and boutique shops of Queen Street. Nearby to Centennial Park as well as Bondi Junction. Your ideal Woollahra pad. "Sydney's hidden White Lotus" Guest comment!

Woollahra Home with Idyllic Secret Garden

Sunshine flows into all parts of this beautiful 4 bedroom Woollahra terrace. A unique, private and very comfortable home with high ceilings and French doors which open onto an idyllic north garden stretching the full length of the property offering endless space to entertain or relax. Adjacent to Cooper Park’s beautiful walking tracks and 500m to Westfield and Bondi Junction transport network this home is perfectly positioned to explore Sydney. Queen street shops and Bondi Beach are close by.

Stylish Art Deco apartment

Double Bay is a stylish harbourside enclave on the foreshore of Sydney Harbour. The apartment is located in a charming and very well kept art deco building. Marmle entry, wooden panels all this is part of the typical charm of the building. Our apartment is very well kept and has everything you need for a comfortable stay. As we love to sleep well while we are away from home we invested in a first quality bed, mattress and a very quiet sleeping bed room :)! Love a good bed and quietness!

3 Bd home with pool and fireplace heart of Bondi

@fernplaces Unbeatable location with a 2 minute walk to Bondi Junction shopping centre + transport. Charming Spanish style home, multiple living spaces, stacking doors connect to courtyard + pool. Amazingly stocked fireplace in living and bedroom as well as airconditioning. - 3 Bedrooms (King, Double and King Single) - Heated Pool - 2 Fireplaces - Informal dining + living areas flow, entertaining + pool - Euro gas appliances, open-plan kitchen - Daikin split system airconditioning

Luxurious & Huge Warehouse Conversion

HUGE Luxury 4 bedroom warehouse conversion where every bedroom enjoys the comfort of a King bed & it’s own private full size bathroom to ensure the comfort of all guests during their stay. Unique in designed, this home offers near 7m ceilings, an abundance of natural light and immense privacy in lush surrounds right in the centre of it all. Paddington is home to Sydney’s finest restaurants, designers, bars & cafes & sits between Sydney CBD & a variety of Sydney’s best beaches.

The Art Flat, Woollahra

The Art Flat, Woollahra is the perfect bolt hole to explore Sydney's Eastern Suburbs. Found at the rear of a gracious Victorian residence - 'Edgemont’ - it is a charming two bedroom apartment with garden views. A joy to stay at with modern amenities. It is a 10-15m walk to Westfield Bondi Junction, Edgecliff station, Paddington & Double Bay. There is unmetered parking on Wallaroy Rd. There are 2 sets of exterior stairs from street level down to the flat.

Spicer House - Woollahra Village

NEW to the Cobbold & Co luxe house portfolio. Please read our other reviews and know we are so excited to welcome Spicer House to the delightful Woollahra Village. Nestled in a peaceful pocket just moments from Woollahra Village, this architecturally designed terrace offers a chic and luxurious escape. Impeccably styled by a renowned fashion designer, the home is a sanctuary of comfort and elegance, perfect for couples or friends seeking a memorable getaway.

3BR Woollahra Family Stay with Parking

This is a QUIET RESIDENTIAL PROPERTY. PARTIES, EVENTS, AND EXCESSIVE NOISE ARE STRICTLY NOT PERMITTED. Escape to a charming Woollahra terrace just moments from Centennial Park. This light-filled home welcomes up to 7 guests across 3 bedrooms, including a private attic retreat, plus a sofa for an extra guest. Enjoy relaxed living and dining areas, a leafy courtyard perfect for morning coffee or evening wine, and secure parking for 1 car. An ideal Sydney base.

Paddington Parkside

Super quiet, ultra convenient, walk to everywhere location, this apartment provides the ultimate Paddington pad handy to Oxford St shops & restaurants, Centennial Park, historic pubs, the SCG, Allianz Stadium & a 30 min easy walk to the CBD. Tucked away to the rear of the building with a northerly aspect, it is very quiet, private and bathed in natural light. It features modern, recently renovated interiors and is dressed in fresh neutral décor.

Old Money Luxury in Double Bay + Parking

✨10% off 7+ nights 🔥20% off 28+ nights ✨Free private Parking A sun-filled 2-bedroom apartment in a grand heritage building, blending classic charm with modern comforts. Features include a fully equipped kitchen, modern bathroom, separate toilet, laundry, balcony, and unique Asian-inspired interiors. Located near Redleaf Beach, scenic bay walks, boutiques, and top dining—perfect for a relaxed, stylish stay.