
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon rentals with a pool
House rentals with a pool

Sage Cottage
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

X Lanzerac - Luxurious 4 bedroom house with solar
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!

Newly renovated, dreamy 3 bedroom house with Solar
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.

Magnificent views / luxurious setting- Sérendipité
Great accommodation. The place is beautiful. I would stay again anytime. Very responsive host. Walkable to Main Street restaurants and the grocery store.

Ocean Retreat, Romansbaai Beach & Fynbos Estate
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.

Large 5 Bed, 5 Bath house, centre of Franschhoek.
What a stunning home. The hosts were easy to contact and answered any queries quckly. It was a perfect stay

Heuningkloof Eco Cottage Greyton
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!!

Akademie House - your home from home
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

Beachfront Apartment with sea- and mountain views
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.

Cliff Path Cottage
Friendly hosts and great place to stay. Very clean and easy access. Would definitely recommend!

Unique Stay at The Den Stellenbosch
Very cosy space. Perfect for a short stay. Also enjoyed the snacks 😋. Would definitely recommend to anyone.

Stunning 3-Bed on the Strand Beachfront
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 .

Hermanus Waterfront Apartment No.19
Nice place to stay. lovely cool room

Thyme Out - Private Apartment
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.

Franschhoek - A Sensory Escape 78 Huguenot
A short walk to the wine tram and restaurants. Flat is very well-equipped and has everything you need.

Avemore Vineyard View with full backup power
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

The Salt Box Villa - Self catering - Strand
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!

Villa in the Vineyard near Somerset West
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.

Eclectic Family Home near Wineries
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.

Harbour Studio
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
- Hermanus Holiday rentals
- Stellenbosch Holiday rentals
- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
- Breerivier Holiday rentals
- Betty's Bay Holiday rentals
- Overstrand Local Municipality Holiday rentals
- Camps Bay Beach Holiday rentals
- Paarl Holiday rentals
- Greyton Holiday rentals
- Yzerfontein Holiday rentals
- Cape Town Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Voëlklip Beach
- Babylonstoren
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Idiom Restaurant & Idiom Wine Tasting Centre
- Waterkloof Wine Tasting Lounge
- Somerset West
- De Zalze Golf Club
- Worcester Golf Club
- Fernkloof Nature Reserve
- Paserene Wine Farm & Wine Tasting in Franschhoek
- Grotto Beach (Blue Flag)
- Bugz Family Playpark
- Grotto Beach
- Klipgat se Plaat
- Haut Espoir
- Banhoek
- The Cellar
- Die Plat
- Druk-My-Niet Wine Estate
- Arabella Golf Club
- Agulhas National Park