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Holiday 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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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, 144 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!

Top guest favourite
Large glass doors open to a serene view of a natural pond, framed by soft drapes. A cozy seating area is visible, with a plush sofa adorned with neutral cushions. Outside, a small bistro table and chairs are positioned on the lawn, enhancing the tranquil setting.
Farm stay in Worcester
4.98 out of 5 average rating, 122 reviews

Lily Pond

Lily Pond, is a luxurious guest house just an hour and a half from Cape Town. Lily Pond is set on a natural pond brimming with incredible bird life, creating a serene atmosphere unmatched anywhere else. With no other cottages in sight and located on a picturesque wine farm, it offers a rare blend of privacy and luxury. The indulgent outdoor bath overlooking the pond, combined with the beautiful walking trails, enhances the sense of peace and seclusion, making this retreat truly one of a kind.

Top guest favourite
Home in Franschhoek
4.99 out of 5 average rating, 198 reviews

Mongoose Manor by Steadfast Collection

With the trifecta of privacy, location (on an equestrian estate) and dynamic design, this home ticks all the boxes for an idyllic stay in the winelands. Not only does it feature interiors by a top designer and breathtaking mountain and valley views, but full solar power and a location mere minutes from the town centre (as well as museums, galleries and wine estates) make it both distinguished and convenient. There is even a friendly water mongoose named Tilly who might drop by to visit.  

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, 221 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.

Guest favourite
A bright seating area features large windows that allow natural light to fill the space. A brown leather couch and a matching armchair are positioned on a red patterned rug, complemented by decorative cushions with vibrant patterns.
Guest suite in Courtrai
4.95 out of 5 average rating, 111 reviews

Protea Suite - in the garden

The Protea Suite is nestled in the leafy neighbourhood of Courtrai in Southern Paarl. A spacious open plan area including a kitchenette ,lounge and king size bed. A clothes rack and hand basin are also in the open area. The bathroom consists of a shower and toilet. Guest have a private entrance and shared use of the swimming pool There is parking on premises, smart TV ,Wi-Fi and Netflix. Protea is close to restaurants, coffee shops ,Paarl Mall and numerous well known wine farms

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, 135 reviews

Heidi's Child, 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 charming private stoep features two rattan chairs positioned beside a small table, inviting relaxation. Natural light filters in from the adjacent large doors, leading into the cottage. Lush greenery and a low garden wall offer a serene view of the surroundings.
Guest house in Paarl
4.87 out of 5 average rating, 236 reviews

Pepperpot Cottage in Paarl

Tranquil and serene, Pepperpot Cottage is a hidden gem situated in the historical centre of Paarl. The tiny 22 square meters is stylish and quaint with its own entrance and off street parking for one vehicle. It is completely private and guests are welcome to come and go at leisure. It has all the luxuries to make your stay relaxing and memorable with a lush view from the stoep across the garden, farm style pond and vegetable patch of our work in progress garden.

Superhost
An inviting bedroom features a queen-size bed with decorative pillows and a textured green throw. Nightstands with lamps are positioned on either side, while the geometric-patterned wallpaper adds a stylish touch to the serene space.
Farm stay in Paarl
4.8 out of 5 average rating, 200 reviews

Orchard Corner Cottage

LOADSHEDDING - FREE UNIT (Inverter) Orchard Corner Cottage offers a self-catering stay on the working farm, Minie, in the Paarl district. It's the ideal accommodation for leisure, romantic and even business travellers looking for a serene, central base while exploring the numerous wine farms in the area or even when attending a wedding at the surrounding wedding venues. Come and escape the ordinary and enjoy the majestics that Orchard Corner Cottage offers.

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.
Apartment in Paarl
4.86 out of 5 average rating, 238 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 serene outdoor space features a sparkling pool surrounded by lush greenery. Sun loungers are positioned beside the water, while trees provide natural shade. The home is visible in the background, blending harmoniously with the tranquil garden setting.
Guest suite in Milnerton
4.98 out of 5 average rating, 104 reviews

Beautiful country house set in lush garden

This stylish home located near the Wellington town center, schools, Huguenot College and CPUT, is hosted by Antoinette. It's the ideal spot for professional long stays, parents of students, wedding guests or explorers of the winelands looking for accommodation in the beautiful country town of Wellington, South Africa. [This property do have a back-up power system, therefor guests won't experience any loadshedding.]

Top guest favourite
An expansive terrace features a private splash pool with a wooden deck, overlooking stunning views of the mountains and cityscape. Floor-to-ceiling sliding doors connect the terrace to the modern interior, allowing for seamless outdoor access from the en-suite bedroom area.
Flat in Tamboerskloof
4.99 out of 5 average rating, 304 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 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
4.98 out of 5 average rating, 469 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

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Avg. price$95 SGD$98 SGD$103 SGD$100 SGD$98 SGD$91 SGD$93 SGD$85 SGD$102 SGD$98 SGD$98 SGD$113 SGD
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Quick stats about holiday rentals with a pool in Wellington

  • Total holiday rentals

    Explore 80 holiday rentals in Wellington

  • Nightly prices starting at

    Wellington holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Wellington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellington rentals

  • 4.8 Average rating

    Wellington stays are highly rated by guests – averaging 4.8 out of 5!