
Holiday rentals with a pool in Caledon
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Caledon

Total holiday rentals
Explore 20 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 300 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Caledon holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Caledon rentals
Top-rated rentals with a pool in Caledon
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.
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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.
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Cottage on Fir Hermanus
Superb non-smoking garden cottage at the back of the main house. It sleeps 4 guests in two very luxurious en-suite double bedrooms (Air conditioned) with spacious TV- lounge and small kitchenette. (Well equipped). Expect good quality linen and fluffy towels and unexpected little luxuries. A sparkling pool, free parking and Fibre Wi-Fi on the premises. Guests can enjoy the garden and pool at leisure. It is completely separate and private as only one other person resides in the main house.
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Oceanfront Villa 4br/4ba pool wifi, solar power
Whale Huys is a Self-catering, direct oceanfront villa with panoramic views of Walker Bay and the Klein Rivier Mountains. Perfect for a relaxing holiday away, just 2 hours from Cape Town. With its stunning views and just the sounds of nature, Whale Huys seems far removed from the busy hustle and bustle of our daily lives. but is close to the wineries and renowned country restaurants the area is famous for. Outdoor and cultural activities abound. Just 5 min. from Gansbaai for shopping.
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Blueberry Hill Cottages - Lavender - Franschhoek
Lavender Cottage is a modern three bedroom self catering cottage with three bedrooms, main ensuite and the other two bedrooms share a full bathroom. There is a fully equipped kitchen with cooker, microwave and Nespresso coffee maker. The cottage has its own private terrace overlooking the large rim flow pool. The pool is situated on it's own large terrace and is shared with Olive cottage. We are ideal for guests who enjoy wine tours, the outdoors, hiking and biking plus horse riding.
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Potato Patch Self Catering Cottage
This versatile thatched roofed cottage is centrally located in a private setting offering contemporary country comfort with a dash of history. It is one of the two cottages located on the owners property with its own entrance and secluded garden. The cottage consists of 3 en suite bedrooms furnished with king sized beds. The rates are based on 2 people sharing a room. Using additional rooms comes with an additional charge. Pets are permitted on request at an additional charge.
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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.
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Bellevlei Estate | The Rock House
Welcome to our spacious, independent and stylish 1-bedroom retreat, located on the Blauwklippen road just minutes from Stellenbosch. The Rock House is perfect for taking in the sights of the historical town of Stellenbosch, mountain biking trails or a quick round of golf. Although shops and restaurants are only a five-minute drive away, the area feels peaceful and secluded. Whether you're here for a weekend getaway or a longer stay, the Rock House has all that you need.
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Misty Shores Cottage
Located on the seafront and in a biosphere reserve, Kalliste’s Misty Shores Cottage is a self catering, private and freestanding cottage of Kalliste Beach House (owner's accommodation). Misty Shores Cottage offers magnificent views of the mountain on the one side and the ocean on the other side. The property is surrounded by indigenous gardens, making the cottage ideally suited to those seeking a connection with nature, and a space in which to relax and recharge.
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Luxury apartment Kandinsky with panoramic views
High-quality luxury apartment for 2 people in Somerset West, prime location. 10 m long panoramic glass front overlooking mountains and sea. The apartment has a living area with kitchen, bathroom and one bedroom. A Nespresso machine, toaster, kettle, hair dryer, towels and linens are available. Extra long king size bed and TV. Pool and outdoor area are available for shared use and sauna and jacuzzi can also be offered by arrangement.
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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.
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The FAIRY FLYCATCHER (Lucky Crane Villas)
The Fairy Flycatcher is part of LUCKY CRANE VILLAS - a collection of contemporary meets country villas in the picturesque village of McGregor with the best views in town. Romance rules in this one-bedroom sanctuary for a single guest or a couple. Complete with outdoor bath and an intimate natural pool and nestled in an olive orchard with uninterrupted views, this is honeymoon-perfect!
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Popular amenities for Caledon rentals with a pool
House rentals with a pool

Magnificent views / luxurious setting- Sérendipité
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De Villiers House
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Luxurious comfortable 4 bedroom beach house
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Stylish Cozy Cottage in Voelklip ( 2 to 6 people)
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Beautiful Beach Breakaway
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Mongoose Manor by Steadfast Collection
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The heart of Franschhoek
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Paloma Villa, Franschhoek | Pool & Fireplace
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Condo rentals with a pool

Cliff Path Cottage
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The Yacht, Pat's Place Hermanus
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J Spot • Safe & Convenient • Backup Power
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Unique Stay at The Den Stellenbosch
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Villa Verde, farm stay with views for days.
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25 Whale Rock Estate
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Avemore Vineyard View Le Verger
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Hermanus Waterfront Apartment No.20
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Home rentals with a private pool

The Salt Box Villa - Self catering - Strand
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Eclectic Family Home near Wineries
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Villa in the Vineyard near Somerset West
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Harbour Studio
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When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $123 NZD | $120 NZD | $89 NZD | $116 NZD | $126 NZD | $128 NZD | $93 NZD | $93 NZD | $110 NZD | $111 NZD | $111 NZD | $89 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
- Stellenbosch University
- Babylonstoren
- Jonkershoek Nature Reserve
- Cavalli Estate
- Grotto Beach (Blue Flag)
- ATKV Goudini Spa
- Voëlklip Beach
- Waterkloof Wine Tasting Lounge
- Idiom Restaurant & Idiom Wine Tasting Centre
- Fernkloof Nature Reserve
- Hermanus Beach Club
- Rust en Vrede Wine Estate
- Babylonstoren Wine Estate
- La Motte Wine Farm & Restaurant
- Boschendal Wine Estate
- Haute Cabrière - the home of Pierre Jourdan
- Kolkol Mountain Lodge
- De Hollandsche Molen
- Kogelberg Nature Reserve
- Delaire Graff Estate
- Tokara Wine Estate
- Somerset Mall
- Spice Route Destination
- Stark-Condé Wines





