
Holiday rentals with a pool in Southern Highlands
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southern Highlands
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Nostalgia Retreat- Panoramic Views
Take in the extraordinary views from our comfortable one bedroom cabin adjoining the stunning Kangaroo Valley Golf Course. Nostalgia Retreat has a new queen size bed with quality bed linen ,wall mounted TV and claw foot bath.There is a separate shower, Air conditioning ,Foxtel and parking for two cars wifi Swimming pool ,tennis courts and restaurant are available for guests enjoyment . Kangaroos and wombats are on your doorstep . 5 Mins drive from KV village,cafes ,shops and historic bridge.

"Seacliff" - Cliff Top Beach House
"Seacliff Otford" is just 60mins from Sydney CBD yet feels a million miles away. The house is on 2 acres, perched on the top of a hill, enjoying panoramic ocean views. Living areas face north enjoying all year sun . The lounge includes a log fire. There is a separate TV room, 4 double bedrooms, 2 bathrooms. The property includes a heated swimming pool (in summer) with large deck, lawned areas and a tennis court. STRICTLY 8 PEOPLE MAXIMUM, NO PARTIES, BUCKS WEEKENDS OR FUNCTIONS.

The Treehouse Kangaroo Valley on Kangaroo River
The Treehouse offers picturesque Glamping perched over Kangaroo River in the Heart of Kangaroo Valley. It has a beautiful large stone outdoor bath to soak in set amongst the canopy of the gum trees. The Treehouse Kangaroo Valley sleeps up to 4 adults(2 couples) or really close friends & is an ADULTS ONLY retreat. We offer great value as we use Airbnb Smart Market Pricing. PETS: considered on application only. Enquire PRIOR TO BOOKING for our T and C to see if your pet qualifies.

Little Alby - Luxe Tiny Home
Little Alby is our luxe Tiny Home located in Callala Beach, the heart of Jervis Bay. Privately nestled amongst a stunning bush outlook and only steps to the beach. Watch the stars twinkle through the above bed skylight and let the sound of the waves lul you into a deep sleep. Our guests will indulge in luxurious linens and products from an array of premium brands including a special collaboration with Lurline Co, ensuring an exceptional and aesthetic experience.

Wake up to the ocean at LegaSea
LegaSea is a self contained Guest House overlooking the historic Shellharbour boat harbour and coastline. Guests will feel as though they are levitating directly over the glistening waters of the calm harbour and can observe the activity of the nearby village from a comfortable, luxurious space. Village cafes and amenities are a short stroll away, and the beach or famous cowries surf break is at your doorstep. Find us on Instagram @Legasea_shellharbour

Breathe again, Cabin cuteness, entire cottage
This is a little piece of heaven, a moment for some tranquillity nestled within the Kangaroo Valley Golf Retreat located on the Golf Course. A short stroll to the pool. Volleyball. court all walking distance. 2 new tennis courts Walking distance to volleyball court, Giant chess set Badminton court & Swimming pool. Dive in. Quality inclusions. We are 4km from town. Single nite stays permitted.

ARUNA Estate off-grid cabins
ARUNA Cabins provide the ultimate off-grid experience. Nestled amongst the Australian Scribbly Gums, it offers a bush view, down to the River. If you want to get as far as possible from the bustling world, the ARUNA cabin is for you. Custom built for their bush location, our cabins provide a stylish and snug escape. They are completely off grid so you can ensure your total freedom from the everyday.

Exclusive Mt Hay Retreat, Berry
Multi Award winning, family owned and operated Mt Hay Retreat is unique, private and ultra exclusive. A boutique escape that is simply second to none. With only a handful of individual residences, each luxury suite is filled with natural light and has been designed as your own private escape. Please note that we are unable to welcome guests aged under 18 years or pets of any kind.

New Mercer cottage at Silvermist
Mercer Cottage at Silvermist — a light-filled, contemporary retreat with vaulted ceilings, designer touches, and sweeping mountain views. Relax on the sun deck, dine outdoors, take a dip in your private plunge pool, and unwind by the fire pit. Perfectly located between Berry’s boutique cafés and the golden sands of Seven Mile & Gerroa Beaches.

The Annexe at Beatrice Park, Bowral
Welcome to The Annexe at Beatrice Park Perfect for Couples or Solo Travelers Nestled within the heritage-listed gardens of Beatrice Park, The Annexe offers a private retreat ideal for a weekend escape or an extended stay. Whether you're here for leisure or business, you’ll find The Annexe a tranquil and comfortable home away from home.

Martha's Villa - panoramic, peaceful location
Please note, as Martha’s is advertised across multiple platforms and is able to be booked directly by searching for Martha’s Kangaroo Valley, your booking is not confirmed until you receive a booking confirmation from Airbnb. Treat yourself to an unforgettable, ambient escape with breathtaking views at all times of the day.

Spacious Unit on Horse Property
Self-contained,attached,modern,spacious, 1 bedroom unit with kitchen on picturesque horse property. Dam, chicken coop, vegetable garden, use of inground pool and BBQ.10min to historic Berrima, 15 to Bowral & Mittagong. Close to Vineyards and Horse Trials. 2hrs to Canberra, 1.5hrs to Sydney Airport. 1.15hrs to SIEC.
Popular amenities for Southern Highlands rentals with a pool
House rentals with a pool

SeeView on Minerva

Rea Rea Lodge | Couples Pavilion Retreat Option

BEACH-FRONT! Luxury House with Pool & SPA

Sutton House Southern Highlands

Entire Detached Property with Pool

Cuttaway Cottage

BEACH OASIS family home with pool at the Beach

Wollemi House - in forest and waterways with pool
Condo rentals with a pool

The Pacific View Studio Penthouse Suite

Absolute Beach front accommodation.

Golf View Villa Bowral

"Orana" to The 'Gong

Stylish 1 brm apartment central location

Coastal Rainforest Retreat
Other holiday rentals with a pool

Husky Getaway - Villa with Heated Plunge Pool

That Beach Shack - Tranquil Pool & Beach Getaway

3 BR Newly Renovated Private Farmhouse

Farm stay at Melaleuca cottage

Allambie Gums... a resting place

Contemporary country 89 acre farm home with pool

The Farmhouse Pool Studio , The Barn Stormhill

Sails On Wentworth: your luxury seaside escape.
Destinations to explore
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- Rentals with a fire pit Southern Highlands
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- Wollongong Beach
- Werri Beach
- Bulli Beach
- Coledale Beach
- Austinmer Beach
- Windang Beach
- South Beach
- Wombarra Beach
- Warilla Beach
- Minnamurra Beach
- Bombo Beach
- Jamberoo Action Park
- Towradgi Beach
- Sea Cliff Bridge
- Bowral Golf Club
- Jones Beach
- Corrimal Beach
- Sharkies Beach
- Red Sands beach
- Easts Beach
- Kendalls Beach
- Nowra Aquatic Park
- Kiama Surf Beach
- Goulburn Golf Club




