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, 134 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

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 Courtrai

4.94 out of 5 average rating, 171 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, 208 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 favorite

A serene outdoor area features a swimming pool bordered by natural stone. Lush greenery includes several trees, providing shade and a natural backdrop. The distant mountains create a peaceful atmosphere, enhancing the connection with nature.

Cottage in Cape Winelands District Municipality

4.99 out of 5 average rating, 102 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 favorite

A serene pool area is surrounded by lush greenery and potted plants. The pool's tranquil water reflects the natural surroundings, while a covered outdoor space is visible in the background. The scene evokes a sense of relaxation and cohabitation with nature.

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 favorite

A serene swimming pool is surrounded by lush greenery, featuring a patio area with wooden lounge chairs. White columns create an elegant entrance to the pool area, which is framed by vibrant flora, providing a tranquil space for relaxation.

Condo in Paarl

4.86 out of 5 average rating, 213 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.

Top guest favorite

Apartment in Spanish Farms

4.99 out of 5 average rating, 165 reviews

Luxury apartment Kandinsky with panoramic views

High-quality luxury apartment for 2 people in Somerset West, prime location. 10 m long panoramic glass front overlooking mountains and sea. The apartment has a living area with kitchen, bathroom and one bedroom. A Nespresso machine, toaster, kettle, hair dryer, towels and linens are available. Extra long king size bed and TV. Pool and outdoor area are available for shared use and sauna and jacuzzi can also be offered by arrangement.

Guest favorite

Home in Wolseley

4.93 out of 5 average rating, 103 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, 285 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, 421 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

A well-lit sleeping area features a spacious bed with crisp linens and supportive pillows. Wooden bedside tables with lamps provide soft lighting. A wooden dining table with a vase of flowers serves as a focal point, complemented by muted wall decor displaying a neutral pattern.

Guest suite in Groenvlei

4.95 out of 5 average rating, 155 reviews

Sol Montis Guest Cottage

Newly built cottage at the foot of Paarl Rock Mountain with a private entrance and courtyard with braai facilities. Centrally located between Paarl Mediclinic, St Stephen’s Oncology Centre and Paarl Gymnasium. This flatlet has free WiFi, DSTV and a well-equipped kitchenette. Come and enjoy your stay in a clean, homely cottage in a quiet neighbourhood.

Top guest favorite

A modern guesthouse is mirrored in the serene water of a pond, surrounded by green lawns and trees. The structure features a spacious terrace with outdoor seating, inviting relaxation and views of the clear blue sky and distant mountains.

Vacation home in Wolseley

4.98 out of 5 average rating, 137 reviews

Orchard Stay

We offer country living at its best. A self-catering guesthouse nestled between pear orchards, Orchard Stay offers you space and freedom inside and out. Comfort is a priority in this two bedroom farm house with both rooms having en-suite bathrooms and wow factor views of the orchards and Mostertshoek Mountain.