
Vacation rentals with a pool in Caledon
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Top-rated rentals with a pool in Caledon
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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

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.

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.

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.

"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.

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.

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.

*Central - Whale Watching Paradise -Self check in*
In the Central hub of Hermanus opposite the old harbor, close to all activities & amenities, the local market, restaurants & shops all in walking distance, this apartment's location is key! Free parking space, art galleries, whale museum and the whale coast walking path boast all views for whale watching, convenience is right at your doorstep. Wi-Fi, Netflix and many more offers this stunning spacious apartment offers!!

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.

Great escape with breathtaking view
# Totally off grid Farm house, Situated on a mountain side with the best views of the Babilongstoring mountains, lagoon and Arabella golf estate - only 9km's from Hermanus central. On the Karwyderskraal road off the R320- with 14 wine estates for wine tasting on your doorstep. With plenty of fresh mountain, drinking water.Maximum 6 guests Children welcome Non-smoking villa NO PETS ALLOWED
Popular amenities for Caledon rentals with a pool
House rentals with a pool

Sage Cottage

Seaside Sanctuary

X Lanzerac - Luxurious 4 bedroom house with solar

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

Heron House - self-catering with pool

Magnificent views / luxurious setting- Sérendipité

Tockie's: An idyllic & historic 2-bedroom cottage

Luxury 5 Bed House in the Heart of Franschhoek
Condo rentals with a pool

17 Marine Penthouse/Private Pool/Solar Powered

Cliff Path Cottage

Unique Stay at The Den Stellenbosch

Hermanus Waterfront Apartment No.20

Stunning 3-Bed on the Strand Beachfront

Avemore Vineyard View with full backup power

Kalliste Boutique Stays, Whale Walk Apartment

J Spot • Safe & Convenient • Backup Power
Home rentals with a private pool

The Salt Box Villa - Self catering - Strand
Villa in the Vineyard near Somerset West

Eclectic Family Home near Wineries

Harbour Studio
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $78 CAD | $73 CAD | $75 CAD | $78 CAD | $82 CAD | $76 CAD | $76 CAD | $76 CAD | $90 CAD | $75 CAD | $76 CAD | $75 CAD |
| 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 |
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

Verified guest reviews
Over 270 verified reviews to help you choose

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
Destinations to explore
- Cape Town Vacation rentals
- Plettenberg Bay Vacation rentals
- Hermanus Vacation rentals
- Langebaan Vacation rentals
- Stellenbosch Vacation rentals
- Knysna Vacation rentals
- Franschhoek Vacation rentals
- Southern Suburbs Vacation rentals
- Mossel Bay Vacation rentals
- Betty's Bay Vacation rentals
- George Vacation rentals
- Breerivier Vacation rentals
- Babylonstoren
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Waterkloof Wine Tasting Lounge
- Grotto Beach (Blue Flag)
- Idiom Restaurant & Idiom Wine Tasting Centre
- Fernkloof Nature Reserve
- Voëlklip Beach
- Cavalli Estate
- Worcester Golf Club
- De Zalze Golf Club
- Bugz Family Playpark
- Klein-Drakensteinberge
- Arabella Golf Club
- Agulhas National Park
- Grotto Beach
- Die Plat
- Die Gruis
- Haut Espoir
- Tokara Wine Estate
- Boschendal Wine Estate
- Nederburg Wines
- Druk-My-Niet Wine Estate
- Babylonstoren Wine Estate




