Vacation rentals with a pool in South Wairarapa District

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Top-rated rentals with a pool in South Wairarapa District

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Top guest favorite

The Villa is situated amidst expansive vineyard rows, showcasing a modern design that blends with the landscape. Generous decks extend from the structure, offering outdoor seating and views of the surrounding greenery. The backdrop features rolling hills under a clear blue sky.

Home in Martinborough

4.98 out of 5 average rating, 40 reviews

Southdown Villa

Welcome to our Villa in the vines just 5 minutes drive from Martinborough. We recently completed development of the Villa capturing spectacular views in all directions and creating a stylish space that provides rest, relaxation, and wonderful alfresco dining. The Villa is comprised of two parts - a three bedroom main house, and a separate two bedroom cottage. While we live in the Cottage, we make available to guests our three bedroom House, along with access to all exterior Villa amenities.

Guest favorite

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.

Home in Martinborough

4.94 out of 5 average rating, 113 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.

Top guest favorite

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

4.98 out of 5 average rating, 571 reviews

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.

Top guest favorite

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

5 out of 5 average rating, 238 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 220 reviews

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.

Superhost

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

4.92 out of 5 average rating, 327 reviews

Spring is here.

Modern settler cottage on historic Wairarapa property. Hosted by Brigid and Richard. Sleeps up to 8, DIY breakfast. Well-equipped kitchen. Continuous hot water. Unlimited Wifi, gas barbie, spa pool, brazier pit, trampoline, 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. EV charger on site. Quiet cottage in garden setting.

Top guest favorite

A clear blue heated pool is surrounded by a paved deck area, featuring multiple sun loungers for relaxation. Nearby, a dining table and grill area are visible, set against a backdrop of lush greenery and fencing, creating a private outdoor space.

Guest suite in Greytown

4.97 out of 5 average rating, 104 reviews

Apt Le Petit. Ideal for a quiet getaway.

Very private and petit but centrally located with a 2 minute walk to the Greytown shops. Ideal for dining out or that morning brunch, with all restaurants and cafes within strolling distance. Perfect location for wedding 'bus pick ups' Although attached to the main house, you have your own separate entry to the apartment which is situated in lovely garden surrounds. There is plenty of off street parking and if you’re feeling energetic there are 2 bikes available.

Guest favorite

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.

Home in Martinborough

4.95 out of 5 average rating, 133 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, and Tennis Court.

Top guest favorite

A cozy lounge area is presented with a mix of seating options, including a grey sofa, a vibrant red couch, and a leather chair. Decorative wall art adds color, while natural light filters in through the windows, creating a bright and inviting ambiance.

Apartment in Masterton

4.96 out of 5 average rating, 194 reviews

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.

Guest favorite

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.

Guesthouse in Martinborough

4.98 out of 5 average rating, 149 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

Top guest favorite

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

5 out of 5 average rating, 119 reviews

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!

Top guest favorite

A spacious room features a large glass sliding door that opens to a private pool area. Sun loungers are set near the inviting blue pool, accompanied by umbrellas for shade. A Nespresso coffee machine is visible on a white side table, with neutral-colored decor creating a serene atmosphere.

Guesthouse in Greytown

4.96 out of 5 average rating, 23 reviews

Greytown Urban Retreat

Welcome to "Greytown Urban Retreat' our little peace of centrally located paradise. You will love our peaceful oasis, surrounded by lush greenery just 5 minutes walk to the stylish, boutique village of Greytown. Perfect for Summer and Winter - modern, new & double glazed. Pool, outdoor loungers, pickle ball and a fan for the summer and Spa, heater, books, board games for winter. Plus…’Cherry on the top’ - Outdoor Fire for all seasons!