Holiday houses in Woollahra

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Top-rated holiday rentals in Woollahra

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

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Top Guest favourite
A bright master suite features a spacious bed with a light green throw. Large glass doors open to a balcony, providing extensive views of the surrounding area. The room includes a comfortable seating arrangement with stylish chairs, a desk, and a floor mirror.
Apartment in Randwick
5 out of 5 average rating, 215 reviews

A stylish and well located 2-level loft apartment

Located in a cul-de-sac, this apartment is at the front of the property and enjoys extensive views from both balconies. Private stairs from street level take you to a bright open-plan living and dining area with a fully equipped kitchen. The area opens to a large balcony with a gas barbecue. Another staircase takes you to an equally bright airy master suite. The modern bathroom has a shower, large spa bath and double sinks. There is a television on each level and a Sonos sound system throughout.

Top Guest favourite
Condo in Mosman
4.98 out of 5 average rating, 190 reviews

Absolute Harbourfront Apartment with Fabulous Panoramic Views

Magnificent piece of paradise at the waters' edge. Heart stopping views from every room (Guest 2017) Bright & sunny, idyllic waterfront sanctuary Separate home office All linens and unit professionally cleaned Alfresco balcony perfect for drinks/meals BBQ dining, sun lounges, harbour pool Onsite parking: max. car height 1.7 metres Bus & ferry close Fireworks often seen, spectacular on New Year's Eve & Australia Day Peaceful by day, stunning by night Come and chill out – you won't want to leave!

Guest favourite
An architecturally unique home features a striking angular design with large glass windows that reflect warm light. The exterior combines metal and textured surfaces, framed by a quiet street and greenery, showcasing a modern, inviting entrance.
Tiny home in Centennial Park
4.86 out of 5 average rating, 132 reviews

Centennial Park Ultra Stylish Close to Beach/City

ULTRA STYLISH Home NOW WITH AIR-CONDITIONER Free-standing STATE OF THE ART located in quiet safe leafy cul de sac ARCHITECTURALLY UNIQUE North facing Cool, airy, light-filled, separate living + sleeping + Indoor/outdoor space Perfect for FILM peeps: FOX studios, 30 min walk/10 min cycle thru park 1 min WALK- CENTENNIAL/QUEENS PARKS, 8 min drive-Bronte beach, 10 min walk-Bondi Junction/trains 10 min to city On street parking available & free Designed for working, relaxing + attractions

Guest favourite
A modern living area features a large, light-colored sectional sofa paired with two comfortable armchairs. A round mirror reflects natural light from a wall of windows providing ocean views. A coffee table made of marble adds elegance, surrounded by greenery and decorative accents.
Apartment in Vaucluse
4.97 out of 5 average rating, 122 reviews

Stunning 1bdr w/ Amazing View

Bright and airy one bedroom apartment nestled on top of Diamond Bay Cliffs with breathtaking ocean views. The stunning view overlooking the cliffs and the soothing sound of waves, provide an incredible connection to the ocean from awe inspiring sunrises to frolicking whales throughout the day. Relax with a wine or coffee in this beautifully styled home surrounded in comfort and serenity. Take a dip in the pool overlooking the ocean or take a walk along the cliff walkway. Free street parking

Guest favourite
A bright living space features a comfortable grey sofa adorned with orange and grey cushions. A wooden dining table with chairs is nearby, accompanied by a small television and a decorative rug. Large windows allow natural light to fill the room.
Condo in Double Bay
4.86 out of 5 average rating, 191 reviews

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!

Guest favourite
The living space is illuminated by natural light streaming through large windows. A cozy couch sits beside a wooden coffee table, while a smart TV is mounted on a white console. The bedroom area features a queen size bed, with leafy views visible beyond sheer curtains.
Apartment in Waverley
4.98 out of 5 average rating, 122 reviews

Designer Coastal Apartment

This designer apartment is newly renovated and positioned on the top floor facing N/E nestled amongst the tree tops with ocean glimpses on the horizon. A quiet and private location with free street parking and only a 10 minute walk to the beach. Enjoy Charing Cross with its boutique shops, cafes, restaurants, pubs and public transport. Bondi junction Westfield and train station is an easy 20 minute walk. Busses are available from nearby streets. *Not suitable for children and infants.

Top Guest favourite
A modern kitchen is complemented by green cabinetry and a large white island that includes two wooden stools. Natural light fills the space through sliding glass doors that open to a serene outdoor area featuring lounge seating among greenery.
Townhouse in Bondi Junction
4.78 out of 5 average rating, 243 reviews

Art-Filled Designer Terrace in Chic Woollahra

This unique Heritage-Listed Terrace in the Heart of Woollahra, has a style all of its own. Experience the charm of a heritage-listed terrace house in Woollahra, perfectly situated just moments from Centennial Park and a short trip to the beach. This spacious and stylish two-bedroom home offers a unique blend of comfort, character, and history. Please note: while the house is exceptionally comfortable and full of character, it may not be the best fit for families with young children.

Top Guest favourite
Apartment in Darling Point
4.95 out of 5 average rating, 177 reviews

Luxury Apartment - Harbour and City Skyline Views

Elanora - A Gracious Apartment A historic building but completely reconfigured and renovated. One of only 4 apartments in the building. 130 m² / 1400ft² A large, open timber deck looks out over Rushcutters Bay and through yachts and out to the northern end of theHarbour Bridge. Two generous bedrooms and bathrooms and an open plan living, dining and kitchen space. We are close to beautiful Rushcutters Bay Park and the CYCA. Timber floors throughout, aircondtioning, Foxtel and Netflix.

Top Guest favourite
Guesthouse in St Ives
4.99 out of 5 average rating, 140 reviews

Luxury Garden Cottage Retreat - Romantic & Restful

Arriving through antique gates, wander down wisteria covered walkway to your home away from home. Outdoor tiled undercover area with dining/living space, lit in evenings with silk lanterns invite you outside for a special occasion. Light-filled cottage, open plan living/dining area. Bedroom boasts plush queen bed for a blissful nights' sleep. Bathroom invites indulgence with a rainforest shower. Fully equipped kitchen with washing machine. Thoughtful touches throughout.

Superhost
Guest suite in Paddington
4.8 out of 5 average rating, 535 reviews

BRAND NEW Ultimate Paddington Pad

Set off iconic and heritage listed Paddington Street, the loft is a light and airy self contained studio above the garage (double bed with bathroom) overlooking a lush garden. Accommodation is one block from bus (10mins Bondi Beach, 10 mins CBD), Sydney's best restaurants, Queen Street, Five Ways, Westfield, Sydney Harbour. The space is modern, well designed and perfect for a weeks stay to explore the spectacular harbour city. Walking distance from major attractions.

Guest favourite
An open-plan living and dining area is illuminated by natural light, featuring a modern couch and a round dining table with four chairs. A sleek kitchen is visible in the background. A private balcony with greenery is accessible through sliding glass doors.
Condo in Paddington
4.96 out of 5 average rating, 134 reviews

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.

Top Guest favourite
Apartment in Paddington
4.94 out of 5 average rating, 175 reviews

Spacious 1 Bedroom apartment

Central fully furnished 1 bedroom apartment (ground floor), fully equipped kitchen and own courtyard in a terrace house. We live upstairs. Private secure entrance. Check in 2pm -6pm! Located in the prestigious Queen St. 20 minutes from the CBD and 20 minutes from Bondi Beach. Great buses. 1-2 people. No children (0-12). Wifi Smart TV Please read The Space and Guest Access.

Popular amenities for Woollahra holiday rentals

When is the best time to visit Woollahra?

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Avg. price$309 NZD$238 NZD$257 NZD$220 NZD$199 NZD$198 NZD$201 NZD$213 NZD$214 NZD$245 NZD$257 NZD$326 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Woollahra?

    Woollahra has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Woollahra with our serviced apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Woollahra?

    Four-legged friends are welcome in Woollahra. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Woollahra?

    Yes! Work meets play with ease at over 110 vacation rentals in Woollahra featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Woollahra vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Woollahra, available on Airbnb. Make a splash and soak up the sun in style!

  • Do hotel rentals in Woollahra have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Woollahra. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Woollahra have a kitchen?

    Absolutely! We offer over 10 townhouse rentals with a kitchen in Woollahra. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Woollahra have wifi?

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

  • Do house rentals in Woollahra have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Woollahra. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Townhouse Rentals in Woollahra?

    Enhance your stay in our Townhouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Woollahra

  • Total holiday rentals

    Explore 360 holiday rentals in Woollahra

  • Nightly prices starting at

    Woollahra holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Woollahra holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woollahra rentals

  • 4.7 Average rating

    Woollahra stays receive an average rating of 4.7 out of 5 from guests