
Vacation 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!

Luxury 2 bed Villa & pool, Sandstone, Franschhoek
Lovely 180m2 Villa set in the middle of a vineyard, is elegantly decorated with 2 bedrooms with full bathrooms en-suite. We have an automatic 60kva generator and water supply. The Villa is fully equipped SMEG appliances in the kitchen and laundry, 3 TV’s, Netflix, Apple TV, sound system, Nespresso facilities, air-conditioning etc. The rooms lead onto their own private gardens with sun loungers and private pool. Enjoy a swim, game of tennis, walks in the olives, vineyards and rose garden.

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.

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.

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.]

La Roche Estate Pinot Noir Suite 1
Nestled in the tranquil Robertsvlei valley in Franschhoek lies our luxury vineyard suites with picturesque views of La Roche Estate, Robertsvlei road. 5km away from the centre of Franschhoek and surrounded by many mountain biking/ hiking trails, as well as wine farms . Each suite has their own private wood fired hot tub, fireplace and a welcome basket with bubbly for you to enjoy in this tranquil setting.

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.

Best Elgin views in serene setting with pool
The Annex at Tree Tops, is a spacious and well-appointed garden annex with incredible views, adjoining the main homestead. This is the perfect couples’ retreat in which to recharge your batteries while overlooking the magnificent Elgin valley. Offering a wood-burning fireplace (free wood provided) for winter and a plunge pool for summer.

Orchard Stay
We offer country living at its best. A self-catering guesthouse nestled between pear orchards, Orchard Stay offers you space and freedom inside and out. Comfort is a priority in this two bedroom farm house with both rooms having en-suite bathrooms and wow factor views of the orchards and Mostertshoek Mountain.
Popular amenities for Wellington rentals with a pool
House rentals with a pool

Villa Soleil

Blackwood Log Cabin

Magnificent views / luxurious setting- Sérendipité

Newly renovated, dreamy 3 bedroom house with Solar

Luxury 5 Bed House in the Heart of Franschhoek

Nooks Pied-a-Terre | Architecturally Stunning Home

Mountain House

Paloma Villa
Condo rentals with a pool

African Chic with Incredible Views & Pool Deck

Newlands Peak

3 Bed Penthouse / No Loadshedding / Infinity Pool
Terrace Suite - own pool, jacuzzi bath, fireplace

Contemporary, Sea Point pad, w/ views & inverter

Mountain View Penthouse

J Spot • Safe & Convenient • Backup Power

Sailor’s Away - 3004 - 16 On Bree
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

Chic Penthouse with Private Pool & Breathtaking Views

Majestic Mountain Views from the Patio of a Designer Studio

Upper Constantia Guest House

Stylish Villa, 100m From The Camps Bay Beach

Chic Boutique-Hotel Feel at a Seafront Pad, Clifton
When is the best time to visit Wellington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$15,669 GYD | G$16,087 GYD | G$16,923 GYD | G$16,505 GYD | G$16,087 GYD | G$15,042 GYD | G$15,251 GYD | G$13,998 GYD | G$16,714 GYD | G$11,700 GYD | G$15,042 GYD | G$15,878 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 |
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$2,089 GYD per night before taxes and fees

Verified guest reviews
Over 1,970 verified reviews to help you choose

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

Rentals with dedicated workspaces
30 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!
Destinations to explore
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- 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
- Woodbridge Island Beach
- Hout Bay Beach
- Green Point Park
- Sandy Bay, Cape Town
- St James Beach
- Babylonstoren
- District Six Museum
- Two Oceans Aquarium
- Mojo Market
- Noordhoek Beach
- Durbanville Golf Club
- Jonkershoek Nature Reserve
- Waterkloof Wine Tasting Lounge
- Erinvale Estate Hotel and Spa
- Steenberg Tasting Room
- Idiom Restaurant & Idiom Wine Tasting Centre
- Newlands Forest




