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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.

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Top Guest favourite
An open-plan living area features wooden beams and brick walls, with a spacious dining table surrounded by upholstered chairs. Natural light floods the space through large windows, highlighting the relaxed atmosphere. A staircase leads to a loft area, and a view of the pool can be seen outside.
Home in Franschhoek
4.92 out of 5 average rating, 156 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.

Guest favourite
Large glass doors open to a serene view of a natural pond, framed by soft drapes. A cozy seating area is visible, with a plush sofa adorned with neutral cushions. Outside, a small bistro table and chairs are positioned on the lawn, enhancing the tranquil setting.
Farm stay in Worcester
4.98 out of 5 average rating, 150 reviews

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.

Top Guest favourite
The garden cottage is framed by neatly manicured greenery, with a sparkling swimming pool in the foreground. Sun loungers and an umbrella provide shaded seating. Large glass doors open to a spacious patio area, enhancing the connection between indoor and outdoor living.
Guesthouse in Hermanus
4.99 out of 5 average rating, 267 reviews

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.

Guest favourite
The villa is situated on a hillside surrounded by lush greenery, offering expansive ocean views. Its architectural design features a thatched roof and spacious deck area, which includes a private pool. The surrounding landscape creates a serene coastal atmosphere.
Home in De Kelders
4.94 out of 5 average rating, 139 reviews

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.

Top Guest favourite
A spacious living area is featured with large glass panels offering views of the mountains and sea. A comfortable sofa and armchair are arranged around a coffee table. A dining table is set for four, complemented by decorative plants and fresh flowers.
Apartment in Somerset West
4.99 out of 5 average rating, 179 reviews

Luxusapartment Kandinsky mit Panoramablick

Hochwertig eingerichtetes Luxusapartment für 2 Personen in Somerset West, Bestlage. 10m lange Panoramaglasfront mit Blick auf Berge und Meer. Das Apartment hat Wohnbereich mit Küche, Badezimmer und ein Schlafzimmer. Es steht eine Nespressomaschine zur Verfügung,Toaster, Wasserkocher, Fön, Handtücher und Bettwäsche. Extra langes King size Bett und Fernseher. Pool und Außenanlage sind zur gemeinschaftlichen Nutzung vorhanden und Sauna und Jacuzzi können wir nach Absprache auch anbieten.

Top Guest favourite
A serene outdoor area is showcased with a rim flow pool surrounded by manicured grass and blooming lavender. A large umbrella provides shade over two loungers, while rolling hills and vineyards create a scenic backdrop under a clear blue sky.
Cottage in Franschhoek
4.87 out of 5 average rating, 315 reviews

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.

Top Guest favourite
The open-plan lounge and dining area features a central wooden table surrounded by classic chairs. A cozy seating arrangement with woven chairs sits beside a rustic broom. Light enters through windowpanes, illuminating the clay-tiled floor and highlighting the textural elements of the thatched-roof interior.
Cottage in Greyton
4.87 out of 5 average rating, 296 reviews

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.

Top Guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 170 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.

Top Guest favourite
Home in Stellenbosch
4.89 out of 5 average rating, 108 reviews

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.

Top Guest favourite
Guesthouse in Betty's Bay
4.98 out of 5 average rating, 159 reviews

Misty Shores Cottage - Kalliste Ocean Front Stays

Located on the seafront and in a biosphere reserve, Kalliste’s Misty Shores Cottage is the 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.

Top Guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch
4.98 out of 5 average rating, 524 reviews

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.

Guest favourite
Cottage in Kleinmond
4.81 out of 5 average rating, 250 reviews

The Whale Cottage

Perched on top of a rock formation and nestled amongst its own tiny piece of fynbos and rock heaven, this artists cottage overlooks the mighty Atlantic ocean. With beautiful views of Kleinmond Harbour to the East and the foot of the Kogelberg Mountain and Palmiet River Mouth to the West, this 2 bedroom self-catering home will provide you with the solace only nature can offer.

Popular amenities for Caledon rentals with a pool

When is the best time to visit Caledon?

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Avg. price$124 NZD$121 NZD$90 NZD$117 NZD$127 NZD$129 NZD$93 NZD$93 NZD$110 NZD$112 NZD$112 NZD$90 NZD
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