Holiday houses in South Windsor

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Top-rated holiday rentals in South Windsor

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Top Guest favourite
The spacious balcony features sun loungers and a table setting, offering panoramic views of the beach and marina. A peaceful coastal landscape is visible, with trees framing the scene and boats anchored in the serene waters.
Apartment in Clontarf
4.99 out of 5 average rating, 176 reviews

Harbour Hideaway

Beach front Luxury escape for 2 only. No parties allowed, it is on the lower level of our house, which overlooks Sydney Harbour, It has its own private entrance and is totally separate, it has direct access to the beach in Clontarf, there are 62 steps up to the apartment. We are on the Spit bridge to Manly walk which is stunning. Seaforth Village and Manly are close. Sandy bar cafe at the Marina and Bosk in Park, also a wide variety of first-class dining and shopping options are close by

Guest favourite
An intimate sleeping area features a spacious bed with soft linens, flanked by matching bedside lamps. Wooden beams and rustic decor create a warm ambiance, while a patterned rug adds character. Natural light filters in through a window, enhancing the cozy atmosphere.
Cabin in Bilpin
4.93 out of 5 average rating, 587 reviews

Bilpin Guest House “Cozy Cabin”

Our cosy self-contained cabin is ideal for travelers and couples looking for a short getaway. We are right in the heart of Bilpin . World heritage listed Blue Mountains. The Hive Berambing is a fabulous cafe for Breakfast & Lunch, you can buy Bilpin Bush Honey and local produce. Walking distance to apple picking, The Grumpy Bakery, fine dining at Lochiel House. There is a spa waiting for you when you get back after a long day of Mountain activities and a cosy warm fire. We also offer massage.

Top Guest favourite
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 362 reviews

MontPierre Rustic Cottage-Mountain Hideaway

An Intimate & Rustic, Self-Contained Hilltop Hideaway located on Darug Country, Blue Mountains Designed for relaxation & privacy throughout your stay. The comfortable & cosy accomodation is tailored to romantic, relaxing escapes or a peaceful getaway for two close friends to enjoy a quiet catch up Enjoy the eclectic rustic interiors & indoor fireplace. Private & leafy guest courtyard with firepit, vintage outdoor bath tub, and wood-fired pizza oven for an authentic rustic mountain stay.

Top Guest favourite
Tiny home in Yellow Rock
4.97 out of 5 average rating, 152 reviews

Tiny Bush Escape Blue Mountains

Private Adults-Only Tiny Home | Bush Escape | 1.5hrs from Sydney Looking to truly unwind? This peaceful retreat is tucked away among the trees in the lower Blue Mountains – the perfect spot to slow down, reconnect with nature, and exhale.   Experience the “tiny home” lifestyle in what was once a 40ft shipping container. This beautiful tiny home has been thoughtfully transformed into a luxurious escape for couples, solo travellers, or close friends looking to recharge in privacy and comfort

Guest favourite
A country cabin is positioned amid a grassy landscape, surrounded by trees. The exterior features large windows and a wooden porch with seating. Cows graze peacefully in front of the cabin, and a clear blue sky serves as a backdrop.
Place to stay in Kurrajong
4.71 out of 5 average rating, 196 reviews

Kurrajong Country Cabin Seperate from main home

Need a country escape??? Need a place to relax and unwind? No phone, no tv ,no distractions, just sit back and enjoy listening to nature! Our country cabin is located on acerage in the little suburb of Kurrajong a 4 minute drive to kurrajong village. It is seperate from the main house, it does not have kitchen facilities, however we offer a selection of teas, coffee, toaster and kettle. There is a list of local cafes , convenience store, local restaurants a 4 min drive from our Cabin.

Top Guest favourite
A tiny home is viewed from the outside, showcasing large windows that provide a glimpse of the interior space. Natural wood accents and a small deck area enhance the inviting atmosphere, while surrounding greenery complements the structure.
Tiny home in Wheeny Creek
4.96 out of 5 average rating, 100 reviews

Tiny Love Getaways

Welcome to Tinylove Getaways our tinyhome is located in the beautiful Colo River Valley. With Spa bath , firepit area , in a private bush setting its perfect for a couple looking to relax and unwind. With friendly farm animals including our 4 mini donkeys who love to pop in and greet our guests. Fully self contained with all you need and only 20 mins drive to closest shops and restaurants. Great for a winter escape or a Summer getaway with the colo river only a short distance away.

Top Guest favourite
A covered outdoor area features two wicker chairs set on a wood deck, inviting relaxation. A view into the interior reveals a spacious dining table surrounded by modern chairs, illuminated by soft overhead lighting.
Guest suite in Wahroonga
4.98 out of 5 average rating, 165 reviews

Rainforest Tri-level Townhouse.

Enjoy a peaceful stay in this updated tri-level townhouse, among leafy, tree-lined streets. With its own separate access, off-street parking, and ample safe street parking available, this home offers privacy and convenience. Perfectly located just off the M1 motorway, it’s an ideal stopover along the M1, while also being close to the SAN Hospital, major schools and shopping. Nearby parks, an oval, and bush walks add to the tranquil setting, an ideal base for short or longer stays.

Top Guest favourite
Guesthouse in St Ives
4.99 out of 5 average rating, 123 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.

Top Guest favourite
The studio features a spacious layout with exposed brick walls and wooden accents. A queen bed is centered in the room, accompanied by a cozy sitting area with two chairs. A dining table with two chairs and a well-equipped kitchen are visible in the background.
Guesthouse in Springwood
4.97 out of 5 average rating, 325 reviews

The Bower garden studio retreat

The Bower - garden studio retreat Spacious studio nestled in a large garden which gives onto a lovely natural bush hillside. The Bower is at the end of a cul-de-sac, with no passing traffic, making it quiet and peaceful - perfect for a relaxing break, a romantic weekend or as a base to explore the Blue Mountains. It is an easy 10 mins walk to Springwood township with its many cafes and restaurants and if you are driving, just a few minutes from the highway.

Guest favourite
A heated plunge pool is surrounded by natural bushland, offering sweeping views of the sparkling Hawkesbury River. The outdoor deck features a wooden railing and is bordered by lush greenery, creating a private retreat within the serene landscape.
Home in Patonga
4.93 out of 5 average rating, 135 reviews

Stunning Views, Privacy, Heated Pool & Sauna

Escape to Patonga House, a breathtaking sanctuary nestled on 10 acres of pristine bushland. Perched on a hillside adjacent to National Park, this stunning estate offers eagle-eye views over Patonga and the Hawkesbury River, plus includes a heated plunge pool and a panoramic outdoor sauna. The estate has unparalleled privacy yet is just 2 minutes from Patonga Beach & the iconic Boathouse Hotel. Also nearby, Pearl Beach, another coastal paradise.

Top Guest favourite
The bedroom features a spacious bed with crisp white linens and a green throw blanket draped across the top. Flanking the bed are two bedside tables with lamps. Above the bed, three framed botanical prints are displayed on the wall.
Apartment in Rouse Hill
4.97 out of 5 average rating, 114 reviews

Sylish one bedroom unit overlooking piazza

Modern and stylish one-bedroom apartment @Rouse Hill Town Centre, just steps from the metro which will take you directly to Sydney’s CBD in about 40min. Featuring an open-concept layout, sleek finishes, and natural light throughout, this urban retreat offers both comfort and convenience. Perfectly located with cafés, shops, library and cinemas at your doorstep. Also enjoy the use of a pool, gym and tennis courts a short stroll away.

Top Guest favourite
An outdoor dining area features a wooden table surrounded by six chairs, illuminated by softly glowing candles. A bench with colorful cushions adds comfort. The surrounding deck showcases wooden flooring, and views of lush hills are visible in the twilight sky.
Home in Gunderman
4.96 out of 5 average rating, 103 reviews

Waterfront Treehouse on the Hawkesbury River

Surrounded by national parkland on the Hawkesbury River, the Treehouse is an architecturally designed red-cedar cottage set high on the riverbank with a private jetty and spectacular water views. The two queen beds are furnished with luxurious cotton and Belgian linen. The main bedroom is on a mezzanine level and overlooks the living area which has a slow-combustion fire. Perfect in summer or winter. (Sunday check-out is 5pm.)

Popular amenities for South Windsor holiday rentals