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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 favourite
A charming white cottage is set against a clear blue sky, surrounded by greenery. Wooden windows and a pergola enhance the rustic design. A fence encloses the property, providing an inviting space for outdoor enjoyment.
Cottage in Wellington
4.96 out of 5 average rating, 135 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 favourite
A spacious bedroom features a large bed with soft linens and light blue accents. The room is complemented by built-in cabinetry and a stylish red desk. Natural light filters through two windows, and a decorative chandelier enhances the ceiling's wood texture.
Home in Franschhoek
4.95 out of 5 average rating, 100 reviews

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Lovely 180m2 Villa set in the middle of a vineyard, is elegantly decorated with 2 bedrooms with full bathrooms en-suite. We have an automatic 60kva generator and water supply. The Villa is fully equipped SMEG appliances in the kitchen and laundry, 3 TV’s, Netflix, Apple TV, sound system, Nespresso facilities, air-conditioning etc. The rooms lead onto their own private gardens with sun loungers and private pool. Enjoy a swim, game of tennis, walks in the olives, vineyards and rose garden.

Top guest favourite
A serene outdoor area features a swimming pool surrounded by a stone patio. Comfortable seating and a dining table are visible on the shaded terrace, complemented by lush greenery and distant mountains. The building showcases a light-colored facade with large glass doors that enhance the connection with nature.
Home in Franschhoek
4.99 out of 5 average rating, 183 reviews

Mongoose Manor by Steadfast Collection

This is the most perfect ever listing. Privacy, location, quality. FULLY SOLAR POWERED. Completed by a top designer, breathtaking views of the mountains and wine valley, next to Le Lude champagne estate and restaurant, on an equestrian estate. And under 10 minutes walk to the centre of town, 5 minutes to Le Lude or Haute Cabriere estates, the monument, museum etc. There is even a friendly water mongoose named Tilly who will come to visit! NO CHILDREN of any age allowed, including infants.  

Top guest favourite
A private pool reflects the clear sky, surrounded by a wooden deck and lush greenery. The two-story building is partially visible, featuring large windows that allow natural light. Outdoor seating is arranged under the shade of trees, creating a serene environment.
Guest suite in Courtrai
4.94 out of 5 average rating, 174 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 favourite
A secluded cottage features a stone base with white columns and a dark metal roof. Vines grow over the front porch, which includes two chairs and small tables. Lush green grass surrounds the entrance, enhancing the natural surroundings of vineyards and mountains.
Cottage in Wellington
4.97 out of 5 average rating, 209 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.

Top guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 108 reviews

Heidi's Barn, Franschhoek

Situated on a small holding 5km outside Franschhoek, opposite the exquisite La Motte Wine Estate, Heidi’s Barn offers the perfect self-catering base from which to explore the Winelands. A fire pit, outdoor dining area and a large swimming pool (shared with one other cottage) are perfect for summertime relaxation while an indoor wood-burning fireplace and wooden floors throughout make for a cosy winter escape. The barn runs on mains power with solar back up for load shedding.

Guest favourite
A grassy area is populated with trees and a variety of plants, showcasing a peaceful rural landscape. In the foreground, a dog is seen exploring, while a flock of sheep grazes peacefully in a fenced section. The backdrop features majestic mountains under a clear blue sky.
Home in Western Cape
4.88 out of 5 average rating, 293 reviews

Tranquil poolhouse in the Winelands

Relax, sip on local wines, and take in the spectacular mountain views from the poolside deck. Neighbor to award winning wine farms, situated in the pristine Banhoek Valley. 8 minutes drive to central Stellenbosch, 25 minutes to Franschhoek. Complimentary Tokara wine on arrival with cheese, local nuts and fruits. Basic breakfast supplies provided: coffee, milk, eggs, bread, yogurt, muesli, rusks, orange juice. Bathroom: Soap, shower gel, shampoo, body lotion provided.

Guest favourite
The spacious bedroom features a thatched roof with wooden beams, a large bed dressed in crisp linen, and a decorative throw. Natural light floods the room through large windows, illuminating a small desk and seating area. A cozy rug enhances the warm atmosphere.
Condo in Paarl
4.86 out of 5 average rating, 215 reviews

Shades of Africa - The Studio

Shades of Africa Guesthouse Paarl is a tranquil Cape Dutch styled house set amongst lush gardens offering a private studio apartment with views of surrounding mountains and famous Paarl Rock. Positioned on the Bergrivier within walking distance from the Paarl arboretum and central Paarl the 3rd oldest city in South Africa. Paarl is rich in culture and heritage offering a large variety of culinary experiences and wine farms to choose from.

Guest favourite
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, 104 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 favourite
The spacious living area features a circular couch with neutral cushions, positioned next to large sliding glass doors that offer views of the surrounding mountains. A wooden coffee table with a decorative bowl and magazines is seen in the foreground, enhancing the relaxed ambiance.
Apartment in Tamboerskloof
4.99 out of 5 average rating, 289 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.

Guest favourite
The beautifully structured building features two attached suites with large windows and sliding doors. Each suite is highlighted by an outdoor balcony, providing views of the surrounding landscape. Steps lead to the entrance, complemented by natural stone walls and a terraced garden.
Loft in Franschhoek
4.91 out of 5 average rating, 266 reviews

La Roche Estate Pinot Noir Suite 1.

Nestled in the tranquil Robertsvlei valley in Franschhoek lies our luxury vineyard suites with picturesque views of La Roche Estate, Robertsvlei road. 5km away from the centre of Franschhoek and surrounded by many mountain biking/ hiking trails, as well as wine farms . Each suite has their own private wood fired hot tub, fireplace and a welcome basket with bubbly for you to enjoy in this tranquil setting.

Top guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch
4.97 out of 5 average rating, 431 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.

Popular amenities for Wellington rentals with a pool

Quick stats about vacation rentals with a pool in Wellington

  • Total rentals

    80 properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi