Discover Your Perfect Woollahra Vacation Homes

Why Choose Rent By Owner for your Woollahra Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Woollahra Vacation Rentals

Where are the best neighborhoods to stay in Woollahra?

When exploring Woollahra, Sydney, New South Wales, you’ll discover a charming neighborhood known for its elegant streets and historic charm. Staying in this area offers easy access to boutique shops, fine dining, and beautiful parks, making it an ideal choice for a relaxing getaway. Whether you're seeking a cozy retreat or a spacious home away from home, Woollahra provides a variety of vacation rentals that blend comfort with convenience. This neighborhood's inviting atmosphere ensures a memorable stay, all while being close to the vibrant attractions of Sydney’s eastern suburbs.

Bondi Junction

This vibrant area offers excellent connectivity to the city and surrounds, making it a convenient choice for travelers seeking accessibility to Sydney’s beaches and shopping precincts. Staying here provides easy access to the region's diverse attractions.

View 60+ Rentals in Bondi Junction

Double Bay

Known for its upscale ambiance and waterfront views, this neighborhood is ideal for those wanting a luxurious experience while exploring the region’s chic boutiques and fine dining options. It’s a sophisticated base for your stay in Sydney.

View 28+ Rentals in Double Bay

Paddington

Famous for its historic terraced houses and vibrant fashion scene, this district offers a charming atmosphere with easy access to boutique shopping and cultural spots. It’s a perfect location for an authentic Sydney experience.

View 110+ Rentals in Paddington

Edgecliff

This tranquil neighborhood provides a peaceful retreat with excellent transport links to the city center, making it a practical yet comfortable choice for your stay. Here, convenience meets relaxed living.

View 4750+ Rentals in Edgecliff

Bellevue Hill

Set in an affluent part of the region, this area offers scenic vistas and elegant residences, perfect for travelers seeking a refined atmosphere while still being close to Sydney’s key attractions. It’s a distinguished address for your visit.

View 49+ Rentals in Bellevue Hill

Centennial Park

Surrounded by lush greenery and open space, this neighborhood is ideal for outdoor enthusiasts wanting a relaxing environment near iconic parklands. It provides a peaceful setting within easy reach of the city’s highlights.

View 4500+ Rentals in Centennial Park

Best Times to Visit Woollahra

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you experience this destination's unique charm at its best, whether you're seeking pleasant weather or local events, making it essential to plan your stay accordingly with your preferred vacation rentals here.

Peak Season Highlights

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Spring (September to November)

During the spring, the area comes alive with vibrant greenery and mild weather, making it an ideal time to explore and enjoy the local ambiance through your vacation rental.

Average Temperature Daytime: around 20°C - Nighttime: about 12°C
summer
Summer (December to February)

The summer months bring warmer temperatures and longer daylight hours, perfect for enjoying outdoor activities from your holiday accommodation in this destination.

Average Temperature Daytime: approximately 25-27°C - Nighttime: around 17°C

Off-Season Highlights

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Autumn (March to May)

In autumn, the weather cools slightly, creating a peaceful atmosphere that allows you to experience the region's charm through your vacation rental at a more relaxed pace.

Average Temperature Daytime: about 18°C - Nighttime: roughly 11°C
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Winter (June to August)

Winters are cooler and quieter, offering a tranquil setting to enjoy the local culture and scenic surroundings from your vacation rental during this off-peak period.

Average Temperature Daytime: around 14°C - Nighttime: close to 8°C

Weekly Weather Forecast for Woollahra

How to Book Your Woollahra Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Woollahra

More Top-Rated Vacation Rentals in Woollahra Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor entertaining area perfect for relaxing or hosting gatherings amidst lush surroundings.
  • Benefit from well-maintained gardens and landscaped yards that enhance your outdoor experience in the region.
  • Take advantage of outdoor dining spaces equipped with BBQ grills, ideal for alfresco meals.
  • Make use of dedicated patios or verandas to unwind while soaking up the charming atmosphere of the area.
  • Find accommodations with outdoor seating areas designed for enjoying the local climate and scenery.
  • Explore nearby parks or green spaces that are accessible directly from your rental, offering additional outdoor activities.
  • Relax in private courtyards or backyard retreats that provide a tranquil setting within the region’s peaceful neighborhoods.

Top Attractions Around Woollahra

What attractions are nearby?

In this charming area, you can explore beautiful parks, enjoy boutique shopping experiences, and dine at exceptional local cafes, all just moments away from your chosen vacation rentals in Woollahra, Sydney.

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Family Activities

  • Woollahra Park: Enjoy a family picnic or a relaxing stroll through this picturesque park, perfect for unwinding in the heart of the region.
  • Bondi to Coogee Coastal Walk: Experience breathtaking coastal views on this popular walk, great for families who want to explore the area's natural beauty together.
  • Paddington Markets: Discover unique local crafts and enjoy lively street performances, making it an engaging outing for visitors with children.
  • Australian Museum's Family Exhibits: Spend an educational and fun day exploring Australia's rich history and diverse wildlife in nearby Sydney, offering entertainment suitable for all ages.
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Adult Activities

  • Wine Tasting Tours: Enjoy a sophisticated wine tasting experience at local cellar doors that offer a taste of New South Wales' renowned wine culture right here in the area.
  • Art Gallery Visits: Explore contemporary and traditional Australian art at nearby galleries, perfect for immersing yourself in the region’s vibrant creative scene.
  • Culinary Experiences: Indulge in fine dining establishments and boutique cafes that serve locally sourced ingredients, showcasing the region’s culinary excellence.
  • Historical Walking Tours: Take guided walks through charming streets lined with heritage architecture to discover the area's rich history and architectural beauty.

Other Places to Stay in Woollahra

Akira Boutique
Akira Boutique Vacation Rentals
Queen Street
Queen Street Vacation Rentals
More Places to Stay Near Woollahra

Woollahra Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cafés and Boutiques: Take advantage of the charming local cafés and boutique shops to experience the area's unique atmosphere and support small businesses during your stay.
  • Visit Nearby Parks and Gardens: Make time to relax in the lush parks and gardens, which are perfect for picnics, leisurely walks, and enjoying outdoor tranquility.
  • Discover Cultural Spots and Art Galleries: Immerse yourself in the region’s vibrant arts scene by visiting nearby galleries and cultural landmarks that showcase the area's creative spirit.
  • Plan Your Transportation Options: Consider using public transport or walking to efficiently explore here and make the most of your visit without the hassle of parking.

Transportation Options

  • Sydney Trains: This regional rail network offers convenient access to Woollahra and surrounding areas, making it easy to explore the region without a car.
  • Bus Services: Local bus routes connect the neighborhood to central Sydney and nearby suburbs, providing flexible and affordable transportation options.
  • Taxi and Rideshare Services: Taxis and rideshare providers like Uber operate extensively here, offering a quick and comfortable way to travel within and beyond the area.
  • Walking and Biking: The area's walkable streets and bike-friendly paths allow for enjoyable exploration of Woollahra’s charming neighborhood at your own pace.

Local Customs Options

  • Respect for Local Art and Heritage: You’ll find that appreciating the region’s art galleries and historic architecture is a valued custom here, reflecting a deep respect for the area's cultural heritage.
  • Engaging in Outdoor Social Activities: Participating in alfresco dining and outdoor community events is common, allowing you to immerse yourself in the relaxed lifestyle of this destination.
  • Politeness and Courteous Greetings: Maintaining friendly interactions and greeting neighbors with a warm smile aligns with the courteous manners embraced within the local community.
  • Supporting Local Businesses: Showing support by shopping at local boutiques and dining at neighborhood cafes helps sustain the vibrant small-business scene in this area.

Frequently Asked Questions About Woollahra?

1. What are the top vacation rentals in Woollahra?

There are a lot of options in Woollahra. If you plan on staying in the Woollahra area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Woollahra:

2. Which vacation homes in Woollahra are best for families?

If you are looking for a family-friendly vacation home in Woollahra, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Woollahra:

3. How many Rentbyowner vacation rentals are available in Woollahra?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 63 in the Woollahra area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Woollahra. 

4. What is the cancellation policy for vacation rentals in Woollahra, Sydney?

Cancellation policies vary by listing, so it is important to review the specific terms on the property’s page. Typically, flexible options are available, but some may have non-refundable deposits. For detailed information, contact the property owner directly.

5. How do I book a vacation rental in this area securely?

Booking is straightforward and secure through the platform, which ensures your personal and payment information is protected. Ensure you complete all required steps and communicate with the host if needed before confirming your reservation.

6. Are there any house rules or guest limitations I should be aware of?

Yes, each property has its own house rules and occupancy limits. These will be listed on the individual property page. It’s advisable to read these carefully and contact the host if you have specific questions about your stay.

7. What amenities are typically included in vacation rentals here?

Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and laundry, along with additional features depending on the listing. Details are provided on each property’s page, so review them to find a rental that suits your needs.

8. How can I get assistance if I encounter issues during my stay?

Support is available through the booking platform's customer service. You can contact the host directly for immediate concerns related to the property, and the platform can assist with broader issues before and during your visit.