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Vacation rentals with a pool in Caledon

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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, 592 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, 505 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, 255 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
A serene outdoor area features a swimming pool surrounded by a stone patio. Comfortable seating and a dining table are visible on the shaded terrace, complemented by lush greenery and distant mountains. The building showcases a light-colored facade with large glass doors that enhance the connection with nature.
Home in Franschhoek
4.99 out of 5 average rating, 183 reviews

Mongoose Manor by Steadfast Collection

This is the most perfect ever listing. Privacy, location, quality. FULLY SOLAR POWERED. Completed by a top designer, breathtaking views of the mountains and wine valley, next to Le Lude champagne estate and restaurant, on an equestrian estate. And under 10 minutes walk to the centre of town, 5 minutes to Le Lude or Haute Cabriere estates, the monument, museum etc. There is even a friendly water mongoose named Tilly who will come to visit! NO CHILDREN of any age allowed, including infants.  

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.
Vacation 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, 121 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, 171 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, 261 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, 110 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 grassy area is populated with trees and a variety of plants, showcasing a peaceful rural landscape. In the foreground, a dog is seen exploring, while a flock of sheep grazes peacefully in a fenced section. The backdrop features majestic mountains under a clear blue sky.
Home in Western Cape
4.88 out of 5 average rating, 293 reviews

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.

Top guest favourite
An open-plan living room is furnished with a comfortable couch and decorated with cushions. Large glass doors provide views of the outdoor area, which features a dining set on the stoep. Natural light enhances the airy ambiance, complemented by wooden beams on the ceiling.
Farm stay in Worcester
4.96 out of 5 average rating, 290 reviews

Vineyard House

30km outside Worcester (towards Villiersdorp) The perfect romantic getaway in beautiful and tranquil surroundings. Vineyard House is surrounded by a 360° view of vineyards and mountains. We offer a modern, private stay just outside Worcester, approximately 1½ hours drive from Cape Town. Vineyard House offer a 2 bedroom house (sleeps 4), a bathroom, fully furnished kitchen, livingroom with a fire place and a stoep looking onto the vineyards.

Guest favourite
The beautifully structured building features two attached suites with large windows and sliding doors. Each suite is highlighted by an outdoor balcony, providing views of the surrounding landscape. Steps lead to the entrance, complemented by natural stone walls and a terraced garden.
Loft in Franschhoek
4.91 out of 5 average rating, 266 reviews

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.

Popular amenities for Caledon rentals with a pool

Quick stats about vacation rentals with a pool in Caledon

  • Total vacation rentals

    Explore 20 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at $28 CAD per night before taxes and fees

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  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Caledon vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals