45 Best Vacation Rentals in Woollahra - Holiday Lettings - Cabins

Close

View larger map

Also consider

Edgecliff
21 properties
Double Bay
7 properties
Watsons Bay
5 properties

Woollahra

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

48 Vacation rentals

6

Apartment rental in Woollahra

Greater Sydney / Woollahra

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
- Beautiful leafy suburb close to shops - Parking - WiFi - Strictly no children & no pets - Strictly no subletting without prior written approval from The Apartment Service. Large one bedroom apartment with courtyard. Minutes to Oxford St and Woollahra village lifesty …see more

from $99 / night

$689 / week

Book View

from $99 / night

12

Vacation apartment in Woollahra

Greater Sydney / Woollahra

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Located in chic Woollahra, this exquisite 100m2 executive apartment offers all the luxury and convenience of a hotel stay, with the warmth and character of a private home. 84 Queen St is an executive style rental that has an eclectic countryside feel and features …see more

from $314 / night

$2193 / week

Book View

from $314 / night

(2) Excellent 

22

Vacation home in Woollahra

Greater Sydney / Woollahra

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Car not necessary
Ideal for couples, business travelers, families (with kids & extended family) & within 10 mins walk to Bondi Junction Westfield Mall, Bondi Junction Station, Double Bay, Cooper Park Tennis. 10 mins drive to Bondi Beach, Watson's Bay, Paddington, Sydney CBD, Sydney Opera …see more

from $560 / night

$3654 - $7308 / week

Book View

from $560 / night

12

Vacation villa in Edgecliff

Woollahra / Edgecliff

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
Spectacular views from your lounge room and dining room windows will leave you feeling like you are sitting on top of the world in this fully furnished and well equipped one bedroom, contemporary apartment in stylish Paddington. Located in a tranquil setting, the buildi …see more

from $112 / night

$783 / week

Inquire View

from $112 / night

19

Vacation villa rental

Greater Sydney / Woollahra

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Be wowed by this newly renovated two bedroom apartment, located on the fringe of Paddington and Centennial Park and offering the most amazing sweeping sights over Sydney's famous sporting grounds and entertainment precinct. The views stretch forever and capture the full …see more

from $168 / night

$1175 / week

Inquire View

from $168 / night

18

Vacation villa in Double Bay

Woollahra / Double Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Suitable for children age 5+
Immerse yourself in the startling sights over our amazing harbour from every room in this one bedroom apartment in Darling Point. Whether you are in search of a restful retreat or visiting to reenergize, this home promises to be your perfect place to unwind and relax. P …see more

from $131 / night

$914 / week

Inquire View

from $131 / night

13

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Be captivated by this amazing Darling Point apartment with its fabulous views over Rushcutters Bay and out to the Sydney Harbour Bridge all from the entertainer's terrace. The property interiors have been designed for entertaining with great use of light space and stora …see more

from $187 / night

$1305 / week

Inquire View

from $187 / night

10

Double Bay Vacation villa rental

Woollahra / Double Bay

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
The grand entrance from beautiful Rosemont Ave is a proud prelude what lies within this remarkable 3 bedroom, 3 bathroom over size apartment. Bathed in plenty of sunlight and offering house-like proportions, this magnificent apartment is a rare find within the highly so …see more

from $209 / night

$1462 / week

Inquire View

from $209 / night

15

Home rental in Woollahra

Greater Sydney / Woollahra

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Suitable for children age 5+
Woollahra Terrace is brimming with beautiful features and key attributes but one look at its incredible views over Cooper Park is all you need to fall in love with the stunning property. Visible from the outdoor dining area, and the master balcony, the park is truly a s …see more

from $373 / night

$2610 / week

Inquire View

from $373 / night

19

Villa rental in Double Bay

Woollahra / Double Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
What a lifestyle! Be thrilled by all the wonderful inclusions available in this newly renovated, 2 bedroom apartment in Darling Point. North facing with idyllic views towards the boat-filled Bay and across the Harbour, this spacious apartment features a luxurious new ki …see more

from $187 / night

$1305 / week

Inquire View

from $187 / night

19

Edgecliff Vacation villa rental

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This exceptional apartment is set within the original mansion of an historic converted harbour front estate, gracing the shores of picturesque Elizabeth Bay. Built c1880s and named 'Beau Regard'. Now known as "The Palms', an exclusive collection of 14 luxury apartments. …see more

from $288 / night

$2010 / week

Inquire View

from $288 / night

9

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
This fully equipped 2 bedroom apartment has been updated with new carpet and is freshly painted ready for you to move into this historical part of Paddington, this apartment has everything you need. It has a generous entertaining lounge area and the 2nd bedroom also has …see more

from $131 / night

$914 / week

Inquire View

from $131 / night

19

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
There is plenty to admire on all sides of this beautifully presented 2 bedroom penthouse, situated in the fashionable hub of Paddington. This well styled apartment is just as striking on the outside with a terrace that captures opposing Sydney landmarks from each angle …see more

from $243 / night

$1697 / week

Inquire View

from $243 / night

17

Vacation home rental

Greater Sydney / Woollahra

3 5 5 nights min

  • 3 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
Feel right at home in this fully furnished, architecturally designed three bedroom, two bathroom terrace that spans over three levels providing a vast space that is flooded with light from the many windows. The countless outdoor entertaining areas are a true feature of …see more

from $224 / night

$1566 / week

Inquire View

from $224 / night

14

Vacation villa in Woollahra

Greater Sydney / Woollahra

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Suitable for children age 5+
Enjoy the tranquil surrounds of this adorable one bedroom apartment in the exclusive enclave of Woollahra. You will love the beauty of the stunning liquid amber tree that frames this quaint intimate block typifying life in this ever so elegant address. Once inside, you …see more

from $112 / night

$783 / week

Inquire View

from $112 / night

19

Home rental in Watsons Bay

Woollahra / Watsons Bay

4 8 10 nights min

  • 4 bedrooms
  • Sleeps 8
  • 10 nights min
  • Child friendly
HOLIDAY PROPERTY: Celebrate in this property over the Christmas Holidays Immerse yourself in the Sydney Summer from this stunning four bedroom family home in exclusive Vaucluse, be greeted by a cool and calming ambiance which is created by the rich holiday feel and clea …see more

from $597 / night

$4176 / week

Inquire View

from $597 / night

19

Vacation home in Woollahra

Greater Sydney / Woollahra

4 8 10 nights min

  • 4 bedrooms
  • Sleeps 8
  • 10 nights min
  • Suitable for children age 5+
In an exclusive mews designed by architect Alexander Tzannes, this magnificent four-bedroom home is a short walk from Woollahra's Queen Street shopping village. The classic-contemporary house has a northerly aspect and parklands at the front and rear. Additional feature …see more

from $597 / night

$4176 / week

Inquire View

from $597 / night

9

Woollahra Vacation home rental

Greater Sydney / Woollahra

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
Unusually wide cottage 50 metres from Queen Street. Featuring an unusually wide 6.85 metre frontage, this classic turn of the century cottage has been completely transformed by a stunning renovation, creating a wonderfully spacious, tasteful two-storey home. Set in a qu …see more

from $187 / night

$1305 / week

Inquire View

from $187 / night

(1) Excellent 

19

Vacation villa in Woollahra

Greater Sydney / Woollahra

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Situated in the heart of trendy, cosmopolitan Bondi Junction, this brand-new open plan contemporary apartment is part of the newly developed Aqua twin towers and is bound to be one of the most sought after pads in the Eastern suburbs. The ultra-modern home is compact, f …see more

from $261 / night

$1827 / week

Inquire View

from $261 / night

(1) Excellent 

19

Vacation villa in Edgecliff

Woollahra / Edgecliff

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
Appreciate the very best of Sydney harbour life in this modern, one bedroom apartment which is ideally located opposite the crystal clear waters of Rushcutters Bay. This gorgeous apartment offers a true blend of sophisticated living with the relaxation and calmness affo …see more

from $138 / night

$966 / week

Inquire View

from $138 / night

(1) Excellent 

8

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Friendly, bright and airy this top floor apartment has sensational 270 degree views over Rushcutters Bay in one direction, the city in another and Paddington roof tops in a third direction. It is directly opposite a sunny, open park, only a 2 minute walk to the buzz of …see more

from $112 / night

$783 / week

Inquire View

from $112 / night

24

Vacation home with swimming pool in Double Bay

Woollahra / Double Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A magnificent view should be enjoyed from a comfortable chair in a beautiful room of a superb home and that is exactly how you will enjoy The Harbour View when staying in this opulent Point Piper home. Built circa 1920 with the curves, parquetry floors and high ceiling …see more

from $895 / night

$6264 - $14914 / week

Book View

from $895 / night

24

Vacation apartment rental

Woollahra / Double Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This world-class Point Piper apartment is positioned in Sydneys billionaires playground and Australias most exclusive location. Sure to live up to all expectations, The Sienna boasts some of Sydneys finest harbour views in a setting of sophistication and elegance. Peace …see more

from $3729 / night

$26099 / week

Book View

from $3729 / night

11

Vacation home in Watsons Bay

Woollahra / Watsons Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Come live in our character home, enviously positioned in a sensational address near Rose Bay's premier streets combined with a tranquil cottage like ambiance offers the perfect blend of location and lifestyle. With a short walk to shops and transportation our home is th …see more

from $173 / night

$1205 / week

Book View

from $173 / night

35

Watsons Bay Vacation home rental

Woollahra / Watsons Bay

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
The Space Retreat to this exclusive location and enjoy this 1920’s Historic Beach Bungalow, only a 25 minute drive from the inner city and with transport links close by for you to jump on for a Sydney adventure or corporate visit. With waterfront location & spectacular …see more

from $933 / night

$6525 / week

Book View

from $933 / night

9

Vacation home in Watsons Bay

Woollahra / Watsons Bay

4 7 5 nights min

  • 4 bedrooms
  • Sleeps 7
  • 5 nights min
  • Suitable for children age 5+
This well proportioned property has many delightful qualities that will ensure your stay both comfortable and memorable. Its stunning harbour views, convenient but quite location are all equally impressive as its open space and indoor/outdoor living. Property Features: …see more

from $448 / night

$3132 / week

Inquire View

from $448 / night

11

Vacation home rental

Greater Sydney / Woollahra

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Let the quiet elegance and maturity of a stylish residential house welcome you home with this luxurious four bedroom home located in the peaceful eastern suburb of Woollahra. Woollahra Manor offers you a luxury experience in one of Sydneys finest locations. Only steps a …see more

from $2663 / night

$18642 / week

Book View

from $2663 / night

9

Vacation villa in Edgecliff

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
PRIVATE ROOF TERRACE with HARBOUR VIEWS Get swept away by this ultra-stylish two bedroom penthouse in the high class setting of Rushcutters Bay. With mesmerising views over the spectacular assembly of sailing and cruising boats moored in the famous marina and out to our …see more

from $280 / night

$1958 / week

Inquire View

from $280 / night

19

Edgecliff Vacation villa rental

Woollahra / Edgecliff

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly
Experience the absolute best of our beautiful city from this fully air-conditioned charming two-bedroom apartment. Situated in a lovely tree-lined street in the enchanting suburb of Woollahra, with a calming ambiance and true sense of elegance, this is a space that you …see more

from $187 / night

$1305 / week

Inquire View

from $187 / night

11

Vacation apartment in Edgecliff

Woollahra / Edgecliff

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Welcome to this BKH designed apartment building in Darling Point. Situated on famed New Beach Road Darling Point, opposite Rushcutters Bay Park, the Cruising Yacht Club of Australia and looking out to the Sydney Harbour Bridge, the New Beach Residence is ideally locate …see more

from $1865 / night

$13050 / week

Book View

from $1865 / night

24

Edgecliff Vacation home rental

Woollahra / Edgecliff

4 8 90 nights min

  • 4 bedrooms
  • Sleeps 8
  • 90 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to Mona Vista, Darling Point. This stunning luxury home in Sydney premier location is truly an oasis in the city. Guests will enjoy a unique lifestyle experience that includes spectacular views which pans across Rushcutters Bay, to Sydney Harbour, to the city sk …see more

from $2237 / night

$15659 - $18642 / week

Book View

from $2237 / night

19

Vacation home in Woollahra

Greater Sydney / Woollahra

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Capturing the essence of contemporary elegance, the stylish architect-designed reinvention of this classic terrace has created a unique and incredibly light home on one of Woollahra's signature streets. Crafted with a focus on seamless indoor/outdoor living, bespoke top …see more

from $220 / night

$1540 / week

Inquire View

from $220 / night

15

Vacation home with swimming pool in Watsons Bay

Woollahra / Watsons Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Located in the heart of Watsons Bay and walking distance to the famed Doyles Restaurant, this 3 bedroom, 2 bathroom luxurious home offers you the same view but is close enough for you to order take away. Bathed in sunlight right up until sunset this home not only offers …see more

from $1305 / night

$9135 - $15659 / week

Book View

from $1305 / night

12

Vacation villa in Bellevue Hill

Woollahra / Bellevue Hill

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from $150 / night

$1044 / week

Book View

from $150 / night

16

Vacation home rental

Woollahra / Edgecliff

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Return to the halcyon days of Gatsby at the magnificent Orme Estate Darling Point. This superb 1920's home has been lovingly looked after so it's original features including 10 foot high, ornate plaster ceilings, manicured front and back lawns and gardens and large r …see more

from $3729 / night

$26099 - $36538 / week

Book View

from $3729 / night

20

Vacation apartment in Edgecliff

Woollahra / Edgecliff

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Darling Chic is a superb 2x bedroom 1 bathroom holiday apartment overlooking Sydney Harbour from the top floor of a small block of only 6 apartments and the recent luxurious renovation of modernity pays respect to the apartments 1920s origin. Retaining many of the origi …see more

from $440 / night

$3080 - $5220 / week

Book View

from $440 / night

19

Woollahra Vacation home rental

Greater Sydney / Woollahra

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Child friendly
A showcase of grand scale luxury, this circa 1910 residence 'Lactura' presents stately accommodation of timeless class and impressive all weather outdoor entertaining settings. It's a dual level federation, free standing classic family home with soaring period ceilings, …see more

from $1119 / night

$7830 / week

Inquire View

from $1119 / night

20

Vacation home rental

Woollahra / Edgecliff

2 3 90 nights min

  • 2 bedrooms
  • Sleeps 3
  • 90 nights min
  • Child friendly
  • Air conditioning
Set on a high hill overlooking Rushcutters Bay, Sydney Harbour, and beyond, the Darling Point Pad features extraordinary interiors and sensational viewing decks overlooking a large private garden. This two bedroom apartment has the ambiance and romance of a villa on the …see more

from $1492 / night

$10440 - $15659 / week

Book View

from $1492 / night

22

Vacation apartment in Edgecliff

Woollahra / Edgecliff

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Darling Devine is a beautiful 2x bedroom 1 bathroom holiday apartment overlooking Sydney Harbour from the top floor of a small block of only 6 apartments and the recent luxurious renovation of modernity pays respect to the apartments 1920s origin. Retaining many of the …see more

from $478 / night

$3341 - $5220 / week

Book View

from $478 / night

24

Woollahra Vacation home rental

Greater Sydney / Woollahra

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
TheWoollahra Maison is a stunning Family home in the heart of the Woollahra Village in Sydney's Eastern Suburbs. This sophisticated retreat features three bedrooms in the Main house and a fourth bedroom with ensuite on the other side of the lawn courtyard - perfectly su …see more

from $2237 / night

$15659 / week

Book View

from $2237 / night

1