Vacation rentals with a pool in South Wairarapa District

A large outdoor pool is set within a spacious concrete area, bordered by a sleek stone edge. Lush greenery is visible in the background, offering expansive views of the surrounding rural landscape under a clear blue sky.

4.94 out of 5 average rating, 110 reviews

Martinborough rustic rural retreat.

Wanting a relaxing break away? Look no further than this rural retreat. Situated only 10 mins from Martinborough Square you will find a modern 4 bedroom house with expansive rural views. Have fun swimming in the large outdoor pool (Summer only) or relax in the comfortable outdoor furniture. Enjoy al fresco dining and savour a glass of wine watching the beautiful sunsets. Delight in gazing at the magnificent night sky from the large spa pool. Plenty to see and do with local wineries nearby.

4.98 out of 5 average rating, 562 reviews

A private outdoor area features a swimming pool surrounded by a tiled deck. Lounge chairs are positioned near the pool, and potted plants add greenery to the space. A safety fence encloses the area, offering a scenic view of the surrounding garden.

Yurt in Greytown

Greytown Yurts - Luxurious Glamping Experience

Greytown yurts is luxury accommodation with all the fun and appeal of glamping but with total comfort. There is a ducted heat pump to keep you comfortable all year round. The interior offers a luxurious and calming environment, with beautiful views across our garden. It has a very comfortable king size bed (183 * 203 cm), with superior linen, bedding, towels and robes. A one off cleaning fee and 20% service charge will be added to the price. You can also visit our Greytownyurts online.

5 out of 5 average rating, 232 reviews

A tranquil outdoor area features a clear swimming pool bordered by a concrete patio. Two individuals enjoy the sun, seated on comfortable bean bags near the pool's edge, surrounded by lush greenery and a neatly trimmed hedge in the background.

Barn in Waihakeke

The Good End of the Shed.

A world away from the world -Just 5 mins from Greytown. Situated on a small organic farm in a beautiful garden. Super comfy bed, stylish, mid century decor. Wake up to birdsong, star-gaze from the outside bath while listening to the call of the ruru. Loll by the pool or borrow the bikes to go exploring. Free breakfast of good coffee, homemade muesli & fruit, artisan bread and spreads. Free-range eggs & bacon available for you to cook for $20 pp. Drive on parking, heat pump, wifi & tv.

4.99 out of 5 average rating, 211 reviews

A swimming pool is situated beside a modern cottage, surrounded by the vineyard. The pool area features lounge chairs for relaxation, and a patio umbrella for shade. Lush greenery lines the perimeter, while clear blue skies create a peaceful outdoor setting.

Cottage in Dyerville

Hamden Estate Cottage

Enjoy a stay on our Martinborough vineyard. The cottage is nestled amongst the vines and offers a peaceful retreat from the city. We are 8 kilometres from the centre of Martinborough heading south on the way to Lake Ferry. You can enjoy a leisurely wine tasting at our cellar door with David who is always happy to talk wine. We will also transport you to Martinborough so that you can spend the day investigating local wineries or dine at one of the town's fine restaurants.

4.93 out of 5 average rating, 322 reviews

A spacious swimming pool is framed by wood decking, surrounded by a secure fence and sun loungers. Lush greenery and a large tree provide a serene backdrop, with the cottage visible in the distance under a partly cloudy sky.

Cottage in Upper Plain

Winter is here, enjoy country warmth and comfort.

Modern settler cottage on historic Wairarapa property. Sleeps up to 8 (2 queen double beds and 2 single beds and 2 double sofa beds across 4 spaces), DIY breakfast. Well-equipped kitchen. Continuous hot water. Unlimited Wifi, gas barbie, spa pool, brazier pit, swimming pool, Smart TV, boules, board games, small book/DVD collection. Wander the 40-acre estate - native and exotic trees, orchard, lawns and paddocks. 7 minutes to Masterton by car. Tesla Charging Station on site.

A tranquil saltwater swimming pool is surrounded by landscaped greenery. Two stylish loungers are positioned at the pool's edge, and a wooden deck extends alongside the water. A sunny sky with scattered clouds creates a serene atmosphere in this outdoor space.

4.96 out of 5 average rating, 242 reviews

Black Barn Modern: Luxe Martinborough Escape

Architecturally designed 'modern barn' in Pinot Grove, 900m from Martinborough town centre. Set in a quiet cul-de-sac, this bespoke four bedroom holiday home is a getaway for families, friends, wedding groups and couples. Complete with a chef's kitchen, underfloor heating, fireplace, full-house air conditioning, spa, outdoor living and BBQ. Soak in the spa on the deck or enjoy Pinot Grove's swimming pool. Can’t get the dates you want here? Try https://abnb.me/R9aMPRcSCvb.

Superhost

An aerial view showcases a large rectangular pool surrounded by lush greenery. Adjacent to the pool, an expansive tennis court can be seen, bordered by well-maintained grass. The property features a sleek building and a shaded outdoor seating area, emphasizing open space and natural surroundings.

4.88 out of 5 average rating, 152 reviews

27 Tuscan

Come and enjoy a relaxing stay at our beautiful new home situated at Pinot Grove Estate. Just 900m from the town center with wineries and fabulous restaurants, cafes and a cinema a short stroll away. Full access to a communal 20m heated pool, with separate toddlers pool (open from Labour Day till Easter) or a game of tennis at the all-weather tennis court. Keep the kids entertained with an enclosed trampoline. The large 70sqm deck provides fabulous indoor-outdoor flow.

A spacious outdoor area features a calm, clear pool lined with smooth gray tiles. Surrounded by lush greenery, the setting includes comfortable beanbag seating and a shaded area with a sleek structure. Cloudy skies provide a soft natural light over the scene.

4.96 out of 5 average rating, 118 reviews

Odyssey

Experience the Odyssey! Hot tub spa / Pool table / Beanbags / Cornhole & Outdoor games! This stylish place is perfect for group trips. Featuring four queen beds and ample room in the lounge and dining areas to chill out and socialise with friends. Our place is modern and well equipped with everything you might need to dine in, entertain or simply relax. Booking with us gives you access to shared facilities including, Swimming Pool, Tennis Court and Trampoline.

4.96 out of 5 average rating, 182 reviews

A private courtyard features a shaded seating area with a small table and chairs, surrounded by well-manicured plants and hedges. The swimming pool is visible nearby, complemented by a clear blue sky above and dappled sunlight filtering through the tree branches.

Apartment in Masterton

Fresh oasis near the heart of Masterton

This spacious self-contained apartment is central for Masterton and the Wairarapa region. Town is 800m away & within 20-45mins you can be at Mt Bruce, Castlepoint, Riversdale, or Greytown & Martinborough for vineyards & boutique shopping. Ideal for a couple; with the addition of a king single sofa-bed in the lounge. The bathroom is accessed via the bedroom. Convenient carparking is right on the street, with the option for off-street parking by request.

Guesthouse in Martinborough

A modern guest house is set against a clear blue sky, framed by lush greenery. The building features large glass doors leading to a welcoming interior. A neatly maintained lawn extends in the foreground, enhancing the outdoor setting.

4.98 out of 5 average rating, 146 reviews

Amberley Guest House

Enjoy the best of both worlds! Amberley Guest House is a modern two bedroom self contained retreat nestled on two acres on the edge of Martinborough The guest house has its own entry meaning you can be completely private and independent It offers a welcoming and comfortable lounge, dining and kitchen area with two bedrooms and a modern bathroom Sit back and relax on the large deck with comfy couches and enjoy the setting sun in peace and quiet

5 out of 5 average rating, 118 reviews

A heated pool is surrounded by a clean, tile deck and lush greenery, including trees and flowering shrubs. The pool area is fenced for privacy, with steps leading to the well-maintained grounds, creating an inviting outdoor space.

Guesthouse in Woodside

Cosy Cottage in Greytown

Escape to Pine Grove Cottage, a peaceful country retreat just 1.6km from Greytown village. Built-in 1865, this historic cottage offers a queen-sized bed, ensuite, living area, private patio, heat pump/air con, wifi, and a kitchenette (no cooking facilities). Enjoy cruiser bikes and a heated pool (Nov - April). Attached to the main house but with private access. Discover Greytown's charm and the beauty of Wairarapa. Book now for a serene getaway!