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Holiday rentals with a pool in Wellington

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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
An inviting outdoor living area features comfortable seating and a table, overlooking a private pool. Sun loungers line the deck beside the pool, with the ocean visible in the background. A large awning provides shaded areas, enhancing the space’s relaxation potential.
Home in Camps Bay
4.87 out of 5 average rating, 151 reviews

Glen Beach Bungalow Main House

Soak up sea breezes and uninterrupted views on the expansive wooden pool deck attached to this immaculate modern beach house. Relax on the sun loungers to the sound of the waves. Indoors, stretch out in the open-plan living spaces of two lounge areas - open planned to the kitchen and dining room areas. The Main House level of the beach house is equipped with 4 bedrooms and 4 bathrooms. Three bedrooms are on the ocean level and the 4th master bedroom is downstairs. (The Upper Penthouse level is completely separate to the Main House Level) This Beach Villa - this property is situated directly on Glen Beach. (The small enclave nestled between Camps Bay and Clifton Beaches) Paradise at its best. The open plan kitchen, lounge and dining room open out onto a large decked pool area. Your beach gate leads right onto the beach. Uninterrupted sea views. Glen Beach is uniquely situated with only 15 beach homes. We are within walking distance to the local restaurant strip. The Main House section has 4 bedrooms and can sleep 8. Should your party be larger, the upper penthouse can be combined to allow for a maximum of 12 guests. The Main House is completely private, with it's own private pool. The upper penthouse has it's own pool and balconies. The Beach Gate is communal. Sean, Mary-Louise or another member of our family will be there to check you in and make sure that you are comfortable. We are contactable at all times, should there be any questions needing answers to. The home is situated in the famous international landmark that is Camps Bay. The locale’s crystal clear oceans and soft white beaches—which are within walking distance—draw tourists. Indulge at one of the acclaimed restaurants on the strip. If you want to relax and soak up the sun, walking within the Camps Bay area is easy. Should you wish to explore all Cape Towns other beautiful spots, we recommend to hire a car. This is also extremely easy and can be done at the airport, or once you are at the villa. Cape Town also has a reliable bus system call the Myciti bus. Wifi Bath towels Beach Towels Hairdryers - all included. Please note that a breakage deposit of R20 000.00 will need to be signed on arrival. Please make sure that you have a Master or Visa Credit Card available for this. No Debit Cards accepted. Please note that this villa is for Accommodation only and we do not allow Function Venues. Certain times of the year have a minimum stay attached - please inquire and we will be able to advise.

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, 148 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
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, 132 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.

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
4.93 out of 5 average rating, 197 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 serene outdoor area is showcased with a rim flow pool surrounded by manicured grass and blooming lavender. A large umbrella provides shade over two loungers, while rolling hills and vineyards create a scenic backdrop under a clear blue sky.
Cottage in Franschhoek
4.87 out of 5 average rating, 300 reviews

Blueberry Hill Cottages - Lavender - Franschhoek

Lavender Cottage is a modern three bedroom self catering cottage with three bedrooms, main ensuite and the other two bedrooms share a full bathroom. There is a fully equipped kitchen with cooker, microwave and Nespresso coffee maker. The cottage has its own private terrace overlooking the large rim flow pool. The pool is situated on it's own large terrace and is shared with Olive cottage. We are ideal for guests who enjoy wine tours, the outdoors, hiking and biking plus horse riding.

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, 225 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, 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 wooden cabin is nestled among lush greenery and tall trees, showcasing a welcoming exterior with a covered deck. Large windows reflect the surrounding natural landscape, with the sun casting a warm light on the structure. The adjacent mountains provide a scenic backdrop.
Home in Hout Bay
4.85 out of 5 average rating, 399 reviews

Blackwood Log Cabin

A tranquil and private mountain retreat where water, forest and mountains will re-awaken the soul. Set high on the mountain slopes of Constantia Nek, Blackwood Log Cabin has panoramic views across the lush valley to the mountains beyond. The 2 bedroomed house sleeps 4 with 2 bathrooms. Power outages are being experienced by SA - the oven/stove is gas, the hot water is gas, the internet is solar driven and we have 2 battery lights for guests use.

Guest favourite
A sun-drenched outdoor terrace features a spacious sunbed under a large umbrella. Lush green plants provide a touch of nature, while the sweeping ocean view creates a tranquil setting. Seashell decor adorns the nearby railing, enhancing the coastal ambiance.
Home in Misty Cliffs
4.88 out of 5 average rating, 113 reviews

Shangri La in Misty Cliffs

Shanglira is set on 3 levels with 4 bedrooms and 4 bathrooms ! The fourth bedroom and bathroom being a separate flatlet ! Pool decks , sunsets , barbecues etc are what you want here! Fully equipped kitchen with coffee machines washing machine tumble dryer dishwasher ! Bathrooms all have shower gels etc for you also free unlimited purified water! Pl remember we have doggie beds as well xx NO pets live on the property! But yours are welcome

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 Wellington
4.98 out of 5 average rating, 105 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
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, 476 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 favourite
Home in Franschhoek
4.96 out of 5 average rating, 147 reviews

Newly renovated, dreamy 3 bedroom house with Solar

Enjoy a beautiful artistic home full of character and carefully curated interiors. Don’t worry about loadshedding with the solar and inverter system. All rooms have en-suite bathrooms. The main bedroom has a super king bed, the second room has a queen bed and the third room has a 3/4 bed as well as a bunk bed (2 singles) We really love catering to easy-going guests.

Popular amenities for Wellington rentals with a pool

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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 £7 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!