
Holiday rentals with a pool in Wellington
Find and book unique homes with a pool on Airbnb
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 $18 NZD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Wellington holiday rentals include Wi-Fi 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!
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!

Obiekwa Country House
Obiekwa Country House is located in the picturesque, quaint village of Riebeek Kasteel; with its wine estates and gourmet restaurants. It is set in a quiet cul-de-sac and overlooking an adjoining vineyard. Although it is set in peaceful, rural surroundings, It is a fifteen minute walk to the village square. NO LOADSHEDDING A solar energy system is in place. Please note that advertised prices are for 2 persons sharing a bedroom. If 2 guests would like 2 bedrooms, please book for 3 people.

Nooks Pied-a-Terre | Architecturally Stunning Home
Our stunning home is a 5 min walk into the village and its award winning restaurants, shops and galleries. Black Elephant, Chamonix, Dieu Donne winery's and the famous Winetram are just a short walk away. Nooks is sumptuous, private, cosy, relaxing, full of original art, high ceilings, log fires, beautiful generous spaces and mountain views. Nooks comes alive at night and is great for couples, solo adventurers, who want to be near the soul of this beautiful village. We take up to 4 adults max.

Seaside Mountain Retreat in Misty Cliffs w/ Sauna
Seaside mountain retreat in exclusive Misty Cliffs nature reserve with endless views, pool and large fynbos garden with private path down to the beach. This architect designed wooden bungalow is perfect for exploring Cape Point and the Southern Peninsula or just switching off and relaxing in the verdant immersion of a conservation village. Featuring 2 large en-suite bedrooms as well as a cosy loft and additional bunkbeds for the kids. The house is just 45 minutes from Cape Town city centre.

Admire Sea Views from a Stunning Apartment by Clifton Beach
A perfect haven for couples or individuals seeking a holiday that will be truly memorable. Ezulwini is set in central Clifton, an exclusive area 5 minutes from Town and the V&A Waterfront. The apartment offers unrivalled sea and beach views. The interior is flooded with natural light, beautifully curated in a rich beachside palette of sandy hues with a touch of something nautical. Safety wise, the apartment is a lock up and go and there is battery Back with solar to deal with load shedding.

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.

Vineyard Cottage at Bosman Wines
A serene, beautifully styled cottage with layered textures, soft neutral tones, and thoughtful finishes throughout. It features a cosy lounge, a well-appointed kitchen, and a dreamy en-suite bedroom designed for restful comfort. Set on the 8th generation Bosman Family Vineyards, the cottage offers sweeping vineyard views and an authentic sense of countryside living. A scenic 10-minute walk leads to the cellar, where a complimentary tasting awaits.

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.

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.]

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.

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.

Denneboom Stable Cottage
The cottage offers the charm of reed ceilings and wooden shutters, and an authentic farm atmosphere with private swimming pool. The cottage is situated in a private game reserve and surrounded by Eland, Zebra, Wildebeest & Springbok. This cottage is equipped with solar panels, an inverter and batteries to assist with power during loadshedding.
Popular amenities for Wellington rentals with a pool
House rentals with a pool

De Villiers House

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Blackwood Log Cabin

Magnificent views / luxurious setting- Sérendipité

Bantry Bay Home with Atlantic Ocean Views

Mountain House

Bellevlei Estate | Protea Cottage

Exclusive Tree House Hideaway
Condo rentals with a pool

Stylish 1Bed - Large Balcony/Seaview & Heated Pool

On the Rocks in Bantry Bay
Terrace Suite - own pool, jacuzzi bath, fireplace

Mountain View Penthouse | Secure 2BR, Views & Pool

Amazing Ocean & Mountain Views From Trendy Condo

Modern Ocean View Retreat in Camps Bay

Parker’s Park Lagoon

Modern luxurious sea view apartment
Home rentals with a private pool

Camps Bay Family Beach home with great views.

180• Sea Views from a Hillside Villa, Solar Power

Modern Contemporary Zen Tree House With Pool

Chic Penthouse with Private Pool & Breathtaking Views

Glen Beach Penthouse A on Glen Beach in Camps Bay

Spacious Home - Mountain Views,Pool,Firepit & BBQ

Constantia Klein 4 Bedroom Villa on the Vineyards
Contemporary Farmhouse with Garden and Pool
When is the best time to visit Wellington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 NZD | $161 NZD | $157 NZD | $139 NZD | $136 NZD | $127 NZD | $129 NZD | $118 NZD | $141 NZD | $136 NZD | $136 NZD | $157 NZD |
| 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 |
Destinations to explore
- Cape Town Holiday rentals
- Overstrand Local Municipality Holiday rentals
- Stellenbosch Holiday rentals
- Saldanha Bay Local Municipality Holiday rentals
- Greater Plettenberg Bay Holiday rentals
- Franschhoek Holiday rentals
- Langebaan Holiday rentals
- Plettenberg Bay Holiday rentals
- George Holiday rentals
- Hermanus Holiday rentals
- Knysna Holiday rentals
- Drakenstein Holiday rentals
- Apartment rentals Wellington
- Rentals with a patio Wellington
- Family-friendly rentals Wellington
- House rentals Wellington
- Rentals with outdoor seating Wellington
- Rentals with breakfast Wellington
- Rentals with a fireplace Wellington
- Rentals with a washing machine and dryer Wellington
- Guesthouse rentals Wellington
- Rentals with a fire pit Wellington
- Rentals with pools Cape Winelands District Municipality
- Rentals with pools Western Cape
- Rentals with pools South Africa
- Fish Hoek Beach
- GrandWest Casino and Entertainment World
- V & A Waterfront
- Boulders Beach
- Cape Town International Convention Centre
- Green Point Park
- Glencairn Beach
- Bloubergstrand Beach
- Cbd
- Cape Town Stadium
- Muizenberg Beach
- Stellenbosch University
- Clifton 4th
- Hout Bay Beach
- St James Beach
- Babylonstoren
- Canal Walk Shopping Centre
- Atlantic Seaboard Community
- Noordhoek Beach
- District Six Museum
- Jonkershoek Nature Reserve
- Glen Beach
- Cavalli Estate
- Tyger Waterfront Apartments Deck





