Holiday rentals with a pool in Caledon

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Popular amenities for Caledon rentals with a pool

House rentals with a pool

Guest favourite
Home in Franschhoek
4.8 out of 5 average rating, 341 reviews

Sage Cottage

CatherineRating, 5 stars1 month ago
A lovely spacious house close to the beautiful village of Franshoek, walking distance ! Robyn was very quick to respond to our questions We felt like home and for me is the perfect place if ever we make a new plan for Franshoek ! Thanks Robyn
Guest favourite
Home in Stellenbosch
4.95 out of 5 average rating, 112 reviews

X Lanzerac - Luxurious 4 bedroom house with solar

CharityRating, 5 stars3 weeks ago
We had a lovely stay at Werner's place as two families with 5 adults and 3 kids. The space was the perfect size. Not too big that we felt disconnected from each other, but also not so small that we felt we were in each other's space. It's also a beautiful location, and just a few minutes walk to a winery. Very well stocked in terms of crockery and glassware. Will definitely book again!
Guest favourite
Home in Franschhoek
4.95 out of 5 average rating, 104 reviews

Newly renovated, dreamy 3 bedroom house with Solar

AlexaRating, 5 stars2 months ago
The most amazing house in a fantastic location! We loved everything about it - the decor, the pool. Wonderful house and amazing host. Thank you. We’d love to stay there again if we came back to Franschoek.
Top guest favourite
Home in Franschhoek
5 out of 5 average rating, 107 reviews

Magnificent views / luxurious setting- Sérendipité

JulioRating, 5 stars1 day ago
Great accommodation. The place is beautiful. I would stay again anytime. Very responsive host. Walkable to Main Street restaurants and the grocery store.
Top guest favourite
Home in Gansbaai
5 out of 5 average rating, 47 reviews

Ocean Retreat, Romansbaai Beach & Fynbos Estate

ThomasRating, 5 stars1 month ago
We had the most incredible stay and cannot recommend this place highly enough! From the moment we arrived, Rozanne made us feel completely at home — she’s a truly exceptional host: warm, thoughtful, and always available if we needed anything. The home itself is stunning, with stylish and beautifully curated interior décor that strikes the perfect balance between luxury and comfort. The indoor fireplace was a cozy highlight, and we spent unforgettable dinners at the indoor Braai (bbq) enjoying great food. And the view — absolutely to die for. Waking up to the sight of Springboks and Zebras roaming in the distance felt like something out of a dream. Despite its elegant design, the house was surprisingly child-friendly, making it an ideal getaway for our whole family. Every detail was considered. We’re already thinking of our return — next time, to catch the whales! Thank you again, Rozanne, for everything.
Top guest favourite
Home in Franschhoek
4.94 out of 5 average rating, 141 reviews

Large 5 Bed, 5 Bath house, centre of Franschhoek.

MichelleRating, 5 stars2 weeks ago
What a stunning home. The hosts were easy to contact and answered any queries quckly. It was a perfect stay
Top guest favourite
Home in Greyton
4.95 out of 5 average rating, 22 reviews

Heuningkloof Eco Cottage Greyton

SiobhanRating, 5 stars2 weeks ago
What a beautiful spot! The view is exquisite, it is very quiet and private. So peaceful. The pictures don’t do it justice. Unit is comfortable and we utilised the much needed indoor fireplace. The kitchen has pretty much all you need to make meals. The one bathroom only has a bath, so bear that in mind if you are sharing with others. A magic spot in an awesome location! Susanna was very responsive to requests. We had a wonderful time. Thanks Susanna!!
Top guest favourite
Home in Franschhoek
4.97 out of 5 average rating, 110 reviews

Akademie House - your home from home

RoelofRating, 5 stars5 days ago
This home is a hidden gem! The moment we stepped inside, we felt a warm and cozy atmosphere. The property is beautifully maintained, clean, and tastefully decorated. The location is ideal, with stunning views and a peaceful ambiance. Elaine is an attentive and accommodating host. We loved our stay and would highly recommend this lovely home to anyone looking for a relaxing getaway. 5/5 stars

Apartment rentals with a pool

Guest favourite
Apartment in Strand
4.96 out of 5 average rating, 23 reviews

Beachfront Apartment with sea- and mountain views

NangamsoRating, 5 stars5 months ago
We had an incredible stay at Miriam’s house, from the moment we arrived. We were impressed by the attention to detail and warm welcome The location was perfect, offering both peace and quiet. Also sea view 👌 Our host was responsive, friendly and accommodating, ensuring we had everything we needed.
Guest favourite
Apartment in Hermanus
4.91 out of 5 average rating, 133 reviews

Cliff Path Cottage

CharlesRating, 5 stars3 weeks ago
Friendly hosts and great place to stay. Very clean and easy access. Would definitely recommend!
Guest favourite
Apartment in Stellenbosch
4.99 out of 5 average rating, 83 reviews

Unique Stay at The Den Stellenbosch

NewtonRating, 5 stars2 months ago
Very cosy space. Perfect for a short stay. Also enjoyed the snacks 😋. Would definitely recommend to anyone.
Superhost
Apartment in Strand
4.86 out of 5 average rating, 51 reviews

Stunning 3-Bed on the Strand Beachfront

PearlRating, 5 stars1 month ago
Such an amazing place and host, loved the fact that Colin bought us coffee, juice and milk.. the place is a literal dream and spotless . Colin is always available to respond and assist with whatever , very polite and made it so easy to live in his house .
Top guest favourite
Apartment in Hermanus
4.89 out of 5 average rating, 36 reviews

Hermanus Waterfront Apartment No.19

PieterRating, 5 stars4 months ago
Nice place to stay. lovely cool room
Top guest favourite
Apartment in Somerset West
4.9 out of 5 average rating, 69 reviews

Thyme Out - Private Apartment

RohannRating, 5 stars3 weeks ago
What a pleasure to stay here again! We said we would return and when Somerset West popped up as our destination of choice there was no question about where rather when. The unit felt right at home, access to a beautiful garden with garden furniture, with spacious rooms and bathrooms. Everything one could possibly need! Looking forward to visiting again.
Guest favourite
Apartment in Franschhoek
4.82 out of 5 average rating, 57 reviews

Franschhoek - A Sensory Escape 78 Huguenot

ChanelRating, 5 stars6 days ago
A short walk to the wine tram and restaurants. Flat is very well-equipped and has everything you need.
Superhost
Apartment in Stellenbosch
4.75 out of 5 average rating, 32 reviews

Avemore Vineyard View with full backup power

MarcRating, 5 stars1 month ago
We got extremely lucky when the host offered to upgrade us to the Manor House. Wow. So Spacious and Stylish. An anazing kitchen with absolutely everything you think you need. 3 bedrooms each with their own contemporary bathrooms. The view is breathtaking with early morning coffee. Pizza oven, indoor fireplaces, private hot tub, communal swimming pool, outside braai facilities. There are of course fantastic eateries all over Stellenbosch but this spot is so magnificent that we only went out for breakfast to ensure that we spent as many hours as possible at the house. We only stayed for two nights, and I cannot wait to return. The host was always a call away. What a complete gem.

Home rentals with a private pool

Top guest favourite
Guest suite in Strand
5 out of 5 average rating, 40 reviews

The Salt Box Villa - Self catering - Strand

GraemeRating, 5 stars2 months ago
This was our third time staying at The Salt Box and we had another great stay! The property is beautifully and tastefully decorated and very comfortable. The location is convenient with the beachfront a short walk or drive away. We love the peaceful atmosphere with sliding doors opening the lounge to the private garden / pool area. Dining in is a breeze with everything we needed provided for. The furniture and beds are comfortable and views from upstairs never get old. Ame and Spencer are amazing hosts and are always super responsive and friendly. We also appreciated the thoughtful extras they provide. We are already looking forward to our next stay!
Superhost
Villa in Sir Lowry's Pass
5 out of 5 average rating, 36 reviews

Villa in the Vineyard near Somerset West

DenisRating, 5 stars5 months ago
Lalapanzi and the Skaap House provided an unforgettable two-week retreat for our family of seven. Nestled in stunning natural beauty, the lodge offers breathtaking views that truly felt like a dream. Waking up to the serene landscape each morning was a joy. What truly sets Lalapanzi apart is the opportunity to walk among zebras, springboks, bonteboks, and wildebeest within the game reserve – a magical experience we cherished daily. The warm hospitality and friendly, responsive staff made us feel right at home, and the proximity to fantastic restaurants, wineries, and various outdoor activities was a bonus. We can't recommend Lalapanzi highly enough for anyone seeking an idyllic South African escape.
Top guest favourite
Home in Somerset West
5 out of 5 average rating, 34 reviews

Eclectic Family Home near Wineries

CarolineRating, 5 stars2 months ago
Our trip was made all the more special by our stay in Carol's beautiful home. It was full of wonderful art and artifacts and staying there was one of the highlights of our holiday. We all enjoyed the big, comfortable rooms, the lovely outside dining areas and appreciated all the amenities. The kids loved the sparkling pool and expansive, attractive garden. Carol was so friendly and relaxed and made us feel so welcome. We would wholeheartedly recommend their spot and hope we can stay there again in the near future.
Guest favourite
Serviced apartment in Gordons Bay
4.94 out of 5 average rating, 121 reviews

Harbour Studio

Christyn-LeeRating, 5 stars2 months ago
Parents loved their stay! Definitely go to for future visits

Quick stats about holiday rentals with a pool in Caledon

  • Total rentals

    20 properties

  • Nightly prices starting at

    $26 SGD before taxes and fees

  • Total number of reviews

    280 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore