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Holiday rentals with a pool in Caledon

Find and book unique homes with a pool on Airbnb

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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Guest favourite
An inviting living area features a comfortable gray sofa adorned with decorative pillows. A wooden table holds a vase filled with fresh flowers. Natural light filters in through large windows, illuminating the space beneath vaulted wood-beam ceilings, with a staircase leading to the loft.
Apartment in ZA
4.89 out of 5 average rating, 602 reviews

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.

Top Guest favourite
A small balcony features a round table with a yellow mug and a jar. Two wooden chairs are nearby, and a blanket is draped over one. The scene includes a view of the sea through a wide opening, enhancing the relaxing atmosphere.
Apartment in Hermanus
4.95 out of 5 average rating, 507 reviews

Westcliff Balcony Room

Welcome to this serene and spacious upstairs apartment - with a pool on the one side and a balcony with amazing sea view on the other side. The room itself is warm, cosy and arty. There is plenty of storage, places to sit and relax, access to the pool and safe off street parking. What I love about the room is the feeling you get when you're there... it seems to say 'you're on holiday.. relaaaaxx'. Other 2 apts on the property: /h/westcliff-pool-room-hermanus /h/westcliff-garden-room-hermanus

Top Guest favourite
A private boma area features a fire pit surrounded by colorful rock formations and shrubs. Two lounge chairs with striped cushions face a small table set with wine glasses, offering a scenic view of the distant mountains under a softly lit sky.
Guest suite in Sir Lowry's Pass
5 out of 5 average rating, 258 reviews

Intaba Studio Tranquil Getaway w/style & character

An ideal escape, our Studio is a private, self-catering garden unit located on the mountainside on a 300 Ha farm , with a pool (shared), & beaches closeby (15 min). Off the Grid - own power supply & fresh spring water extracted high in the mountains. Panoramic views over sea and mountain landscapes , surrounded by fynbos and wild birdlife , close to Capetown (55 km), airport, (40km) shopping amenities (7km) . Unwind after a busy day and relax at your private boma or around the pool.

Top 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
4.99 out of 5 average rating, 103 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
Home in Franschhoek
4.99 out of 5 average rating, 188 reviews

Mongoose Manor by Steadfast Collection

With the trifecta of privacy, location (on an equestrian estate) and dynamic design, this home ticks all the boxes for an idyllic stay in the winelands. Not only does it feature interiors by a top designer and breathtaking mountain and valley views, but full solar power and a location mere minutes from the town centre (as well as museums, galleries and wine estates) make it both distinguished and convenient. There is even a friendly water mongoose named Tilly who might drop by to visit.  

Guest favourite
A log cabin is set among green foliage, featuring a spacious wooden deck with a large picnic table and benches. The front porch has comfortable seating and large windows, allowing natural light to flow in. Warm, earthy tones are prominent in the cabin's exterior.
Holiday home in Mereenbosch
4.86 out of 5 average rating, 125 reviews

BushBaby Cabin

BushBaby Cabin is perfect for a romantic get-away. A log cabin beautifully nestled in the milkwood forest, just 20mins from Hermanus - secluded from the busyness of life. Situated by the Botriver lagoon, with a private path for access, this hidden gem brings you to nature's doorstep. Look out for the roaming wild horses and a variety of bird-life. BushBaby is in Meerenbosch with communal pool, tennis courts and table tennis access. Ideal to catch summer sun or a warm, cozy fire in winter.

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
4.93 out of 5 average rating, 122 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.

Guest favourite
A modern architectural home is shown with gray exterior walls and large windows. The entrance is framed by a gravel driveway and surrounded by lush greenery. Outdoor lights gently illuminate the facade, highlighting the inviting atmosphere of the space.
Home in Greyton
4.84 out of 5 average rating, 172 reviews

"Single thorn"

Escape the city and self-isolate in beautiful natural surroundings! Relax and unwind in this wonderful architectural space in the centre of Greyton. Offering fabulous views, an awesome raised pool - and easy walks to the nature reserve and hiking trails. Unfortunately there is a strictly no under-12 and a strictly no pet policy. *** Great attention to hygiene and cleanliness! Note: Price per night includes a maximum of 4 people. Additional guests charged at R250 per person per night.

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
4.86 out of 5 average rating, 264 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, 118 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.

Guest favourite
A cozy bedroom features a spacious bed adorned with various textured pillows and a soft blanket. A nightstand stands beside the bed, with a decorative lamp. Light is filtered through a nearby window, while a folding screen adds privacy to the space.
Condo in Hermanus
4.91 out of 5 average rating, 164 reviews

Cliff Path Cottage

A charming open-plan cottage, nestled near the cliff path and whale-watching lookouts of Hermanus. The freestanding Cottage is situated at the back of a permanent private residence with its own entrance. There is a cosy living area and comfortable seating. It's the perfect spot to unwind after a day of exploring. Adjacent to the living area, you'll find a well-equipped kitchen. No need to worry about loadshedding.

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, 443 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.

Popular amenities for Caledon rentals with a pool

When is the best time to visit Caledon?

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Avg. price$100 NZD$94 NZD$96 NZD$100 NZD$105 NZD$98 NZD$98 NZD$98 NZD$116 NZD$96 NZD$98 NZD$96 NZD
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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 $36 NZD per night before taxes and fees

  • Verified guest reviews

    Over 270 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, Wi-Fi and Pool across Caledon rentals