
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.

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!

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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
House rentals with a pool

Sage Cottage

Blackwood Log Cabin

Newly renovated, dreamy 3 bedroom house with Solar

Tockie's: An idyllic & historic 2-bedroom cottage

Luxury 5 Bed House in the Heart of Franschhoek

Nooks Pied-a-Terre | Architecturally Stunning Home

Akademie House - your home from home

Mountain House
Condo rentals with a pool

African Chic with Incredible Views & Pool Deck

3 Bed Penthouse / No Loadshedding / Infinity Pool

Contemporary, Sea Point pad, w/ views & inverter

Sea-facing Apartment With Amazing Views

Mountain View Penthouse

Sailor’s Away - 3004 - 16 On Bree

J Spot • Safe & Convenient • Backup Power

Canal and palm views apartment
Home rentals with a private pool

180• Sea Views from a Hillside Villa, Solar Power

Glen Beach Bungalow Penthouse

Watch the Sunrise in a Home with a Mountain View

Modern Contemporary Zen Tree With Sparkling Pool

Chic Penthouse with Private Pool & Breathtaking Views

Majestic Mountain Views from the Patio of a Designer Studio
Terrace Suite - own pool, jacuzzi bath, fireplace

Upper Constantia Guest House
Quick stats about holiday rentals with a pool in Wellington
Total rentals
80 properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
70 properties include access to Wi-Fi
Destinations to explore
- Cape Town Holiday rentals
- Plettenberg Bay Holiday rentals
- Hermanus Holiday rentals
- Langebaan Holiday rentals
- Stellenbosch Holiday rentals
- Knysna Holiday rentals
- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
- Mossel Bay Holiday rentals
- Betty's Bay Holiday rentals
- George Holiday rentals
- Breerivier Holiday rentals
- Apartment rentals Wellington
- Guesthouse rentals Wellington
- Family-friendly rentals Wellington
- Rentals with a patio Wellington
- House rentals Wellington
- Rentals with breakfast Wellington
- Rentals with a washing machine and dryer Wellington
- Rentals with a fire pit Wellington
- Rentals with a fireplace Wellington
- Rentals with outdoor seating Wellington
- Rentals with pools Cape Winelands District Municipality
- Rentals with pools Western Cape
- Rentals with pools South Africa
- Glencairn Beach
- Fish Hoek Beach
- Muizenberg Beach
- Big Bay Beach
- Boulders Beach
- Clifton 4th
- GrandWest Casino and Entertainment World
- Hout Bay Beach
- Woodbridge Island Beach
- Green Point Park
- Sandy Bay, Cape Town
- St James Beach
- Babylonstoren
- District Six Museum
- Greenmarket Square
- Mojo Market
- Two Oceans Aquarium
- Durbanville Golf Club
- Waterkloof Wine Tasting Lounge
- Noordhoek Beach
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Steenberg Tasting Room
- Idiom Restaurant & Idiom Wine Tasting Centre