
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.

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!

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.

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.

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.

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

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.

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.

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.

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.

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.]

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

Cook's Cottage : Charming cottage in the village

X Lanzerac - Luxurious 4 bedroom house with solar

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Luxury 5 Bed House in the Heart of Franschhoek

Paloma Villa

The Crescent Hideaway

Rust du Stal
Apartment rentals with a pool

#505 Cartwright - Old World Charm

Peace and Serenity near the Beach at Blue Amanzi

A magical home on the Cape Town Waterfront Canals

Marble Harbour - 1315 - 16 On Bree

Over The Clouds - 3003 - 16 On Bree

Kalk Bay - SeaViews. Patio. Pool. Fireplace. Braai

Contemporary, Sea Point pad, w/ views & inverter

Perfect Views Of Table Mountain and Atlantic Ocean
Home rentals with a private pool

180• Sea Views from a Hillside Villa, Solar Power

Elegant guest wing with own private garden & pool.

Modern Contemporary Zen Tree House With Pool

Harbour Studio

Chic Penthouse with Private Pool & Breathtaking Views
Contemporary Farmhouse with Garden and Pool

Upper Constantia Guest House
Rooftop Pool | Views | 24h power
When is the best time to visit Wellington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
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!
Destinations to explore
- Cape Town Holiday rentals
- Plettenberg Bay Holiday rentals
- Langebaan Holiday rentals
- Hermanus Holiday rentals
- Stellenbosch Holiday rentals
- Knysna Holiday rentals
- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
- Mossel Bay Holiday rentals
- Betty's Bay Holiday rentals
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- Breerivier Holiday rentals
- Family-friendly rentals Wellington
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- Rentals with breakfast Wellington
- Rentals with a washing machine and dryer Wellington
- House rentals Wellington
- Rentals with a firepit Wellington
- Rentals with outdoor seating Wellington
- Rentals with pools Cape Winelands District Municipality
- Rentals with pools Western Cape
- Rentals with pools South Africa
- Cbd
- Atlantic Seaboard Community
- Cape Town Stadium
- Fish Hoek Beach
- Bloubergstrand Beach
- V & A Waterfront
- Muizenberg Beach
- Boulders Beach
- GrandWest Casino and Entertainment World
- Canal Walk Shopping Centre
- Green Point Park
- Clifton 4th
- St James Beach
- Hout Bay Beach
- Babylonstoren
- Stellenbosch University
- District Six Museum
- Noordhoek Beach
- Two Oceans Aquarium
- Jonkershoek Nature Reserve
- Mojo Market
- Newlands Forest
- Steenberg Tasting Room
- Waterkloof Wine Tasting Lounge




