Caledon which includes a small town or village, a park and a pond

Caledon vacation rentals

We found 537 vacation rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of vacation rentals in Caledon that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, including parking and a garden. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Caledon

Showing deals for:Nov 7 - Nov 14

Exceptional

(5 reviews)

Luxury Historic Villa, Best Position In Hermanus with inverter for blackouts!

Hermanus

5% off

includes taxes & fees

Birds eye view of the pool area, 8 chaizes, dining table outside barbeque

Exceptional

(5 reviews)

Awesome Luxury Self Catering ,Child friendly Home ,Superb outdoor living areas.

Hermanus, WC

5% off

includes taxes & fees

Exceptional

(10 reviews)

The ultimate venue to relax & enjoy the views close to restaurants, wine farms,

Cape Town, WC

5% off

includes taxes & fees

Exceptional

(24 reviews)

Studio apartment with sea view and direct view of Table Mountain

Cape Town, Western Cape

10% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Caledon

235 on Tenth near Grotto Beach

Sleeps 6 · 3 bedrooms · 3 bathrooms

Luxury Historic Villa, Best Position In Hermanus with inverter for blackouts!

Sleeps 10 · 5 bedrooms · 4 bathrooms

Top rated rentals - Caledon

Lovely Mountain views in a great neighbourhood

Lovely 4 bedroom 3 bedroom home with great views of fernkloof. Secure and well appointed. A short walk to several beaches and the beach walking trails.

Julie K L.

Stayed Jan 2025

My stay

Fantastic location, friendly service. Historic charm. Only negative, main bedroom bathroom need a bit updating.

stephan v.

Stayed Apr 2023

Absolutely breathtaking views

My wife and I had a most enjoyable two weeks at this property. The unit was very clean, modern, well equipped with a stunning view of Somerset West, Strand and Gordons Bay. Our host, Dorothy, was very helpful and attentive. We will definitely stay here again next time.

Stuart L.

Stayed Mar 2023

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Caledon

Travel to friendly Caledon

Learn about the unique charm of Caledon with a stay in a private vacation home. Travelers appreciate the casino gaming in this welcoming city. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Caledon

Are you hoping to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Caledon a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Gabrielskloof Wine Estate (9.9 mi / 15.9 km)
Cliff Path (17.7 mi / 28.6 km)
Rivendell Wine Estate (13.4 mi / 21.5 km)
SA Forest Adventures (0.3 mi / 0.5 km)
Cold Mountain Vineyard (14.7 mi / 23.7 km)
Bartho Eksteen Wine Estate (16.6 mi / 26.7 km)

Exploring the natural features in Caledon

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Caledon is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

Hemel-en-Aarde Valley (10.3 mi / 16.6 km)
Grotto Beach (14.9 mi / 23.9 km)
Voelklip Beach (14.9 mi / 24 km)
Hermanus Beach (15.1 mi / 24.3 km)
Bot River Estuary (20.4 mi / 32.8 km)
Grootbos Nature Reserve (21.7 mi / 34.9 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Caledon?

Houses are the most popular type of vacation rental in Caledon, according to our data. Even if you've got a different vision in mind, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your ideal match.

How much does it cost to rent a vacation rental in Caledon?

The average price for a vacation rental in Caledon can vary depending on factors including property type, season and length of stay. Whether you're looking for a sprawling house with room for friends and family or a quaint cabin just enough for two, just add your travel dates to discover stays with amazing value.

How much does it cost to rent a beach house in Caledon?

Prices for beach houses in Caledon differ depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use the filters to tailor your search by nearby activities, ratings, amenities and more.

Are there pet-friendly vacation rentals in Caledon?

With six vacation rentals that welcome four-legged guests, your furry best friend can join you on your Caledon getaway. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect pad on Vrbo.

Can I rent a house with a pool in Caledon?

Add an extra layer of fun to your adventure by booking one of the three houses with a private pool in Caledon. Use our search filter to find the kind of property you want on Vrbo, and then spend carefree days splashing and playing in a swimming pool that's just for you.

What are popular rental amenities in Caledon?

Some of the most popular rental amenities people prefer in Caledon are a firepit, a fireplace and a garden. Whether you're on the road with family, pals or even pets, Vrbo vacation homes include the best amenities for making epic memories with the people you cherish the most.

Are there large group vacation rentals in Caledon?

Yes, there are five properties in Caledon that can sleep five or more people. From family reunions to events like a friend's birthday, these stays have enough space to chill out with the people you love.

Are there vacation rentals in Caledon that welcome kids?

Caledon has six family-friendly vacation homes. And booking a stay that welcomes children is a cinch with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll have access to perks and conveniences like living rooms, private pools and yards.

What are the top attractions for families in Caledon?

If the kids are traveling with you, put these family-friendly attractions in Caledon on your list of things to experience:

SA Forest Adventures
Holy Trinity Church

Are there one-bedroom vacation rentals in Caledon?

Take your pick from two one-bedroom rentals in Caledon. Whether you'd prefer a comfy cottage or a condo, our one-bedroom rentals are great if you don't require loads of space. One of the best things about having your own pad? You won't ever have to share your trip with strangers.

How can I find vacation rentals with air conditioning in Caledon?

Select your dates and then make use of our filters to see vacation rentals with air conditioning in Caledon on Vrbo. With three air-conditioned properties on offer here, you can look forward to a cool and comfortable break.

How old do you have to be to rent a vacation rental in Caledon?

The minimum age is typically 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Caledon vacation home before booking.

How long can I rent a vacation rental in Caledon for?

The amount of time you can book a Caledon vacation rental for varies depending on the property. Simply tap in your preferred travel dates to browse options that offer extended stays. They have everything you need to make your extended vacation more convenient and enjoyable, like kitchens and backyards. Some Vrbo vacation rentals may also offer weekly or monthly discounts, so you can hang around longer for less.