
Vacation rentals with a pool in Wellington
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Wellington

Total vacation rentals
Explore 80 vacation rentals in Wellington

Nightly prices starting at
Wellington vacation rentals start at G$4,185 GYD per night before taxes and fees

Verified guest reviews
Over 2,110 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Wellington vacation 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.

Off Grid Getaway with Breathtaking Mountain Views
Greet the day with breakfast before marvelous mountains and countryside views from the sunny balcony. From its vaulted, wood-beam ceilings and country-chic decoration, to its brick-fronted fireplace, this placid hideaway glows with idyllic charm. Set on 2 hectares of beautiful gardens, with fruit trees, vineyards & surrounded by mountains. Sip a glass of chilled wine and enjoy the beautiful sunsets from the large balcony with one of the best views! Cool off in the dipping pool and relax in the tree shaded pool area or on those wet winter days curl up next to the indoor fireplace. Property is gated, guest have there own access and free to roam the property. We like to give guest there own space, however either myself or a staff member are always available and happy to help. Nestled between towering mountainscapes and enduring vineyards, this property is situated in Franschhoek, a town known for its world-class dining, wine tasting, and natural beauty. Visit the Huguenot Memorial Museum to learn about local history. Uber is recently available in Franschhoek but does have a limited presence (after 11pm/12pm). There is also a tuk tuk taxi available, please view enclosed information for contact. Please note there is a friendly young rescue dog that roams freely on the property. Nestled between towering mountainscapes and enduring vineyards, this property is situated in Franschhoek, a town known for its world-class dining, wine tasting, and natural beauty.
4.88 out of 5 average rating, 666 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!
4.96 out of 5 average rating, 154 reviews
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.
4.85 out of 5 average rating, 161 reviews
Magnificent views / luxurious setting- Sérendipité
SOLAR Powered Enjoy breathtaking mountain views from one of the two balconies or curl up next to the indoor fireplace in this spacious open-plan apartment. French doors lead to both balconies that overlook the garden and olive orchard where you can enjoy a barbecue in your own private space. This tastefully furnished with stylish en-suite bathrooms is yours to make home away from home, whilst you enjoy the picturesque winelands and elegant restaurants. Seven minutes walk to the centre of town.
5.0 out of 5 average rating, 122 reviews
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.
4.92 out of 5 average rating, 158 reviews
Vooruitsig Cottage In Paarl
This unique place has a style all its own. Located in the heart of Paarl, on the Paarl Mountain. The cottage has everything you need to enjoy a holiday in the beautiful Winelands with your family or friends. The endless view of the Drakenstein Mountains spread out in front of you with the ever changing colours and shades is mesmerising. The pool in front of the cottage allows for a cool down when needed. The cottage itself is very unique, warm and friendly with mix of old and new.
4.86 out of 5 average rating, 153 reviews
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.
4.99 out of 5 average rating, 182 reviews
Rust du Stal
Nestled in the magnificent Slanghoek Valley. Surrounded by majestic mountains enchanted by peaceful surrounds, you will find Rust Du Stal. The valley offers adventures filled walks, horse riding and mountain bike trails. The valley can be visited throughout the year as each season reveals its own secret beauty. We offer comfortable, fully equipped, self-catering accommodations for your family. With outdoor and enclosed braai areas as well as Wi-Fi access and DSTV
4.82 out of 5 average rating, 159 reviews
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.
4.97 out of 5 average rating, 230 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.
4.87 out of 5 average rating, 258 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.]
4.97 out of 5 average rating, 106 reviews
Denneboom Shepherd's Cottage
In the early 1800s, Shepherd’s Cottage was the home of the sheepherders who cared for the animals on this land. Lovingly restored to modern standards, the Shepherd’s Cottage is now a comfortable luxurious self-catering cottage with a massive indoor fireplace and outside firepit, two en-suite bedrooms, and its very own private plunge pool. The cottage is equipped with an inverter and battery backup for loadshedding.
4.85 out of 5 average rating, 111 reviewsPopular amenities for Wellington rentals with a pool
House rentals with a pool

Walk to Franschhoek Village • Pool • Mountain View
4.87 out of 5 average rating, 127 reviews
Bellevlei Estate | The Rock House
4.89 out of 5 average rating, 114 reviews
Akademie House - your home from home
4.96 out of 5 average rating, 142 reviews
Luxury 2 bed Villa & pool, Sandstone, Franschhoek
4.94 out of 5 average rating, 113 reviews
Spacious Elandsrivier Farmhouse
4.95 out of 5 average rating, 117 reviews
The heart of Franschhoek
4.94 out of 5 average rating, 216 reviews
Mongoose Manor by Steadfast Collection
4.99 out of 5 average rating, 211 reviews
Tockie's: An idyllic & historic 2-bedroom cottage
4.92 out of 5 average rating, 130 reviewsCondo rentals with a pool

Amazing Ocean & Mountain Views From Trendy Condo
4.92 out of 5 average rating, 288 reviews
Spectacular Beachfront Apartment
4.91 out of 5 average rating, 151 reviews
Unique Stay at The Den Stellenbosch
4.99 out of 5 average rating, 105 reviews
Parker’s Park Lagoon
4.91 out of 5 average rating, 169 reviews
Signature Home @ Waterfront Canals
4.96 out of 5 average rating, 110 reviews
16 on Bree | Sailor’s Away | 3004
4.89 out of 5 average rating, 368 reviews
A magical home on the Cape Town Waterfront Canals
4.89 out of 5 average rating, 170 reviews
Kiter’s Dream Villa with garden & garage
4.81 out of 5 average rating, 115 reviewsHome rentals with a private pool

180• Sea Views from a Hillside Villa, Solar Power
4.84 out of 5 average rating, 210 reviews
Hillside Penthouse with Spectacular Table Mountain Views
4.99 out of 5 average rating, 340 reviewsSolar-Powered Mountain Retreat with Natural Pool
4.92 out of 5 average rating, 185 reviews
Chic Penthouse with Private Pool & Breathtaking Views
4.86 out of 5 average rating, 586 reviews
Constantia Klein 4 Bedroom Villa on the Vineyards
4.96 out of 5 average rating, 156 reviewsContemporary Farmhouse with Garden and Pool
4.96 out of 5 average rating, 185 reviews
Top of the World | Opulent Springbok Rd Apartment
4.91 out of 5 average rating, 269 reviews
Rooftop Pool | Views | 24h power
4.9 out of 5 average rating, 227 reviewsWhen is the best time to visit Wellington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$19,041 GYD | G$19,041 GYD | G$18,622 GYD | G$18,831 GYD | G$18,413 GYD | G$17,158 GYD | G$15,274 GYD | G$14,019 GYD | G$16,739 GYD | G$16,111 GYD | G$16,111 GYD | G$18,622 GYD |
| 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 Vacation rentals
- Overstrand Local Municipality Vacation rentals
- Stellenbosch Vacation rentals
- Saldanha Bay Local Municipality Vacation rentals
- Greater Plettenberg Bay Vacation rentals
- Franschhoek Vacation rentals
- Langebaan Vacation rentals
- Plettenberg Bay Vacation rentals
- George Vacation rentals
- Hermanus Vacation rentals
- Knysna Vacation rentals
- Drakenstein Vacation rentals
- Fish Hoek Beach
- GrandWest Casino and Entertainment World
- Cape Town International Convention Centre
- Boulders Beach
- Green Point Park
- Cbd
- Bloubergstrand Beach
- Cape Town Stadium
- Glencairn Beach
- Atlantic Seaboard Community
- Stellenbosch University
- Hout Bay Beach
- Muizenberg Beach
- Canal Walk Shopping Centre
- Clifton 4th
- St James Beach
- Noordhoek Beach
- Jonkershoek Nature Reserve
- Glen Beach
- Cavalli Estate
- District Six Museum
- Newlands Forest
- Table Mountain
- Sea Point Pavilion





