
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

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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.

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.

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

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.

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.

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.

Gledsmuir Spacious Homestead
Magnificent 47 hectare property set on the banks of the Klein River. The Thatched Homestead dates circa 1890’s and boast an ancient Oak Forest. Private and secure. The home offers 7 generous en suite bedrooms, a” Voorkamer”, dining room, two lounges, spacious modern farm styled kitchen in American Walnut plus separate Garden Cottage. The North side of the home features large garden, a covered Veranda with bar overlooking a large 12 metre swimming pool with water features. Book now!

Charming cottage in the Hemel & Aarde Wine Valley
De Werf is in the Hemel en Aarde Valley - literally "Heaven on Earth". It sleeps 6 - large en suite bedroom (king bed or 2 singles) upstairs + a smaller bedroom downstairs (1 outside bedroom en suite on request). Fully equipped kitchen - dishwasher + gas hob opens onto the dining/lounge. Guests relax on the long shady patio with stunning views across to the mountains. A small private swimming pool is perfect for late drinks as the sun sets over the mountains. A birdwatchers paradise.

Luxurious comfortable 4 bedroom beach house
4 bedrooms, all on suite and state of the art amenities. Short walk to Onrus main beach and coastal paths. 5min drive from Hermanus and Hemel and Aarde wine route. Near 2 great golf estates. Open plan areas leading on to panel heated swimming pool. Outdoor entertainment area is decked with a fire pit set amongst beautiful views of the Overberg mountains. Safe and secure with full alarm system, backup electricity invertor system. Quiet and tranquil neighborhood, no parties/loud music.

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.

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.

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.

Luxury apartment Kandinsky with panoramic views
High-quality luxury apartment for 2 people in Somerset West, prime location. 10 m long panoramic glass front overlooking mountains and sea. The apartment has a living area with kitchen, bathroom and one bedroom. A Nespresso machine, toaster, kettle, hair dryer, towels and linens are available. Extra long king size bed and TV. Pool and outdoor area are available for shared use and sauna and jacuzzi can also be offered by arrangement.
Popular amenities for Caledon rentals with a pool
House rentals with a pool

Newly renovated, dreamy 3 bedroom house with Solar

Beautiful Beach Breakaway

Magnificent views / luxurious setting- Sérendipité

Heron House - self-catering with pool

Laleli….The house of Tulips.

Nooks Pied-a-Terre | Architecturally Stunning Home

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

5 Bed Beach Bungalow w/ pool, fire-pit & solar
Condo rentals with a pool

Cliff Path Cottage

The Yacht, Pat's Place Hermanus

Unique Stay at The Den Stellenbosch

J Spot • Safe & Convenient • Backup Power

Villa Verde, farm stay with views for days.

25 Whale Rock Estate

Avemore Vineyard View Le Verger

Serenity Haven - Two Bedroom
Home rentals with a private pool
Villa in the Vineyard near Somerset West

The Salt Box Villa - Self catering - Strand

Eclectic Family Home near Wineries

Harbour Studio
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $123 NZD | $119 NZD | $89 NZD | $116 NZD | $126 NZD | $128 NZD | $92 NZD | $92 NZD | $109 NZD | $111 NZD | $111 NZD | $89 NZD |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
Destinations to explore
- Cape Town Holiday rentals
- Overstrand Local Municipality Holiday rentals
- Stellenbosch Holiday rentals
- Saldanha Bay Local Municipality Holiday rentals
- Greater Plettenberg Bay Holiday rentals
- Franschhoek Holiday rentals
- Langebaan Holiday rentals
- Plettenberg Bay Holiday rentals
- George Holiday rentals
- Hermanus Holiday rentals
- Knysna Holiday rentals
- Drakenstein Holiday rentals
- Stellenbosch University
- Jonkershoek Nature Reserve
- Cavalli Estate
- Grotto Beach (Blue Flag)
- Waterkloof Wine Tasting Lounge
- ATKV Goudini Spa
- Voëlklip Beach
- Fernkloof Nature Reserve
- La Motte Wine Farm & Restaurant
- Babylonstoren Wine Estate
- Boschendal Wine Estate
- Haute Cabrière - the home of Pierre Jourdan
- Kolkol Mountain Lodge
- De Hollandsche Molen
- Kogelberg Nature Reserve
- Delaire Graff Estate
- Tokara Wine Estate
- Somerset Mall
- Spice Route Destination
- Stark-Condé Wines
- Agulhas National Park
- Mont Rochelle Nature Reserve
- Afrikaans Language Monument
- Hermanus Beach Club





