Vacation rentals with a pool in Wellington

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wellington

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

The exterior of the cottage is highlighted by a shaded veranda covered in lush vines. A small pool sits beside the structure, surrounded by greenery. A wooden table and chairs are positioned nearby, inviting guests to relax in the tranquil outdoor setting.

Cottage in Wellington

4.96 out of 5 average rating, 130 reviews

Olifantskop Cottage - Cosy Farm Stay

Enjoy the best of the Cape Winelands in this cosy 2 bedroom (4 people) farm cottage. Situated between two big dams, the cottage offers beautiful views stretching as far as Table Mountain on a sunny day. We allow catch-and-release Bass fishing and you are welcome to take a stroll around the farm to see the cows and many calves that roams next to the dams. The farm is 75 km from Cape Town International Airport and 6 km outside Wellington - the closest town. We'd love to host you on our farm!

Guest favorite

A sunlit outdoor space features a rustic wooden picnic table set against a backdrop of expansive ocean views. The scene is complemented by plants in terracotta pots and distant mountain silhouettes under a partly cloudy sky.

Villa in Simon's Town

4.89 out of 5 average rating, 213 reviews

Cape Point Mountain Getaway - Villa

A magnificent historical home surrounded by fynbos, overlooking False Bay with stunning sea views and an imposing mountain backdrop. The villa is located in a nature conservancy. It is completely off the grid: solar energy, water from a mountain stream. This place is for people who want beauty and tranquillity and a getaway experience in a 100% environmentally friendly place right on the urban edge - 8kms from Simonstown. Fully equipped open plan kitchen, exquisite bedrooms and awesome decks.

Guest favorite

The front exterior of Obiekwa Country House is showcased, featuring a white facade with a sloping metal roof. A covered patio is visible, surrounded by lush greenery, including a neatly trimmed hedge, with mountain views in the background.

Guesthouse in Riebeek-Kasteel

4.85 out of 5 average rating, 139 reviews

Obiekwa Country House

Obiekwa Country House is located in the picturesque, quaint village of Riebeek Kasteel; with its wine estates and gourmet restaurants. It is set in a quiet cul-de-sac and overlooking an adjoining vineyard. Although it is set in peaceful, rural surroundings, It is a fifteen minute walk to the village square. NO LOADSHEDDING A solar energy system is in place. Please note that advertised prices are for 2 persons sharing a bedroom. If 2 guests would like 2 bedrooms, please book for 3 people.

Guest favorite

The private roof-deck features a refreshing plunge pool, with light blue water contrasting against the wooden decking. Expansive views of the surrounding city and hills, including Table Mountain, are visible in the background, providing a scenic backdrop for relaxation.

Loft

4.86 out of 5 average rating, 514 reviews

Chic Penthouse with Private Pool & Breathtaking Views

This light, airy penthouse apartment offers breathtaking views of the city, ocean, Signal Hill, Lions Head and Table Mountain. The private roof-deck offers sensational 360° views, a braai/barbecue and a plunge pool to cool off in and enjoy the wonderful views. The apartment is in a truly wonderful and centrally located City Bowl neighbourhood - Vredehoek. The area is safe, clean, and beautifully situated on the slopes of the famous Table Mountain. It's the perfect base for exploring the city.

Top guest favorite

A spacious bedroom features large glass windows offering panoramic views of the ocean and surrounding greenery. A comfortable chair sits beside the bed, which is adorned with decorative pillows. Natural light fills the room, highlighting the inviting decor and tranquil atmosphere.

Apartment in Clifton

4.98 out of 5 average rating, 348 reviews

Magnificent Clifton Retreat with Unparalleled Ocean Views

A perfect haven for couples or individuals seeking a holiday that will be truly memorable. Ezulwini is set in central Clifton, an exclusive area 5 minutes from Town and the V&A Waterfront. The apartment offers unrivalled sea and beach views. The interior is flooded with natural light, beautifully curated in a rich beachside palette of sandy hues with a touch of something nautical. Safety wise, the apartment is a lock up and go and there is battery Back with solar to deal with load shedding.

Guest favorite

The outdoor area features a wooden deck surrounding a pool, with tropical plants providing natural privacy. A portion of the house, with large windows, is visible, blending indoor and outdoor areas. A small seating arrangement can be seen under the trees, offering shaded relaxation.

Guest suite in Paarl

4.94 out of 5 average rating, 164 reviews

Aloe Suite surrounded by mountains

The Aloe Suite is nestled in the leafy neighbourhood of Courtrai in Southern Paarl. The double story space includes a kitchen, lounge and dining area on the lower level.Upstairs you’ll find a bedroom, en suite bathroom and a balcony overlooking the pool. Guests have a private entrance,patio and barbeque area and shared use of the pool . There is parking on the premises, TV (with netflix ) and Wi-Fi. Laundry can be arranged at a fee. Bed for a minor /child can be arranged on request too

Top guest favorite

Cottage in Wellington

4.97 out of 5 average rating, 203 reviews

Vineyard Cottage at Bosman Wines

Secluded cottage surrounded by vineyards and mountains with romantic, farm-style décor, open-plan kitchen, vineyard-covered front and back porch overlooking the beautiful Wellington wine valley. Fresh white linen bedding, private bathroom and a room with a view of the vineyards and the nursery vines. Small splash pool (cold water) in the backyard, private garage for parking, wine cellar on the farm, we include a complimentary wine tasting. Home to world renowned mountain bike trails.

Superhost

The cottage is situated on a hillside, showcasing an open design with large glass doors leading to a spacious balcony. Surrounding greenery and a stone staircase enhance the natural setting, while the unique architecture blends with the landscape.

Guest suite in Paarl

4.85 out of 5 average rating, 126 reviews

Vooruitsig Cottage In Paarl

This unique place has a style all its own. Located in the heart of Paarl, on the Paarl Mountain. The cottage has everything you need to enjoy a holiday in the beautiful Winelands with your family or friends. The endless view of the Drakenstein Mountains spread out in front of you with the ever changing colours and shades is mesmerising. The pool in front of the cottage allows for a cool down when needed. The cottage itself is very unique, warm and friendly with mix of old and new.

Guest favorite

A modern double shipping container home is situated by a calm dam, showcasing large glass windows that reveal the interior. A wooden deck leads to the water, with a small boat ramp visible. Surroundings include dry, rocky terrain and distant mountains.

Home in Wolseley

4.93 out of 5 average rating, 100 reviews

Trendy private container home! Riverstone House.

Super trendy, double shipping container conversion. Modern, eco& stylish. Perfectly positioned on the dam for afternoon swims &amazing sunset views! Featuring SMEG gas stove, brass fixtures, and Victorian claw foot bath. 2 bedrooms, both ensuite. One with private outside shower. Enjoy a deep shaded patio with built in Bbq, inside and outside dining and lounge. Super cosy for winter with a wood burning closed combustion stove.

Top guest favorite

The spacious bedroom features a large bed dressed in neutral linens and a textured blanket. Floor-to-ceiling glass doors open to a private terrace with city views and potted plants. A cozy armchair is positioned near the windows, inviting relaxation.

Apartment in Tamboerskloof

4.99 out of 5 average rating, 268 reviews

Hillside Penthouse with Spectacular Table Mountain Views

Gaze out on Cape Town from this exclusive retreat high above the city. This quiet cocoon is a place to relax, featuring contemporary furnishings, sliding floor-to-ceiling windows, terrace walkouts, panoramic views of Table Mountain, and a private splash pool. You have an expansive space over two levels to enjoy. Experience the urban buzz or the peace of the great outdoors, both just minutes from the apartment.

Top guest favorite

Farm stay in Stellenbosch

4.97 out of 5 average rating, 394 reviews

Romantic cottage with a pool AND an open air tub!

RiverStone Cottage lies at the foot of the majestic Simonsberg mountain with panoramic views in all directions. Whether you are relaxing under vast oaks or at the plunge pool and watching the sunset turn the mountains pink or are an early bird and watching the sun rise behind cheeky, pointed Botmanskop, there are moments aplenty to ooh and aah at the majesty that surrounds this very special place.

Top guest favorite

Cottage in Franschhoek

4.93 out of 5 average rating, 275 reviews

Kingston Cottage

Kingston Cottage is a self-catering cottage situated 5 km from Franschhoek, neighbouring the beautiful La Motte Wine Farm and close to well-known destinations such Moreson, The Franschhoek Beer Co. and Maison. The property is a smallholding with a main house and additional cottage. It is home to three horses and our much-loved cat after whom Kingston cottage is named.