Simon's Town holiday lettings

We found 143 holiday rentals — enter your dates for availability

Discover a selection of 17 homes, 28 apartments and other holiday rentals in Simon's Town that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as parking and a fireplace. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Why visit Simon's Town

  • Stunning coastal scenery: Enjoy breathtaking views of the ocean and mountains, perfect for outdoor enthusiasts and beach lovers.
  • Rich local culture: Immerse yourself in the charming neighbourhood and experience authentic South African culture.
  • Secluded beaches: Discover hidden gems like Gordon's Bay, ideal for relaxation and romantic escapes.
  • Diverse accommodation options: Choose from charming apartments to luxurious villas that cater to all budgets.
  • Adventure activities: Engage in a variety of outdoor pursuits, from hiking to water sports, ensuring a memorable visit.

Popular types of accommodation around Simon's Town

Planning a getaway to Simon's Town? The excitement starts with selecting your perfect accommodation. From charming apartments and houses to luxurious villas, there's something to suit every taste and budget. Explore a variety of rental options, including flat rentals and house rentals, for a comfortable stay. Whether you prefer a hotel in Simon's Town or a self-catering option, your ideal holiday retreat awaits!

  • Apartments: The top choice for holiday rentals in Simon's Town, offering convenient amenities and a home-like feel ideal for couples or families.
  • Houses: A popular option for those seeking privacy and comfort, perfect for groups or families wanting to enjoy their own space.
  • Villas: Luxurious and spacious, villas provide an upscale experience with stunning views, ideal for a lavish getaway.
  • Cottages: Charming and quaint, cottages offer a cosy retreat amidst picturesque surroundings, perfect for a romantic escape.
  • Condos: A practical choice for travellers, condos combine comfort with great locations, suitable for short or extended stays.**

Top attractions in and around Simon's Town

Simon's Town is an ideal destination for outdoor and beach-loving families, offering a variety of attractions centred around stunning beaches, the picturesque Cape, and majestic mountains. Visitors can immerse themselves in the local culture and enjoy a wealth of outdoor experiences, making it a perfect spot for those seeking relaxation and adventure alike. Whether you're travelling solo, with family, or friends, there’s much to explore in this charming coastal town.

  • Boulders Beach: This stunning beach is famous for its resident African penguin colony. Enjoy sunbathing among the unique boulders and swimming in the tranquil waters, offering a perfect blend of relaxation and wildlife viewing.
  • Table Mountain National Park: A haven for adventure seekers, this national park features breathtaking scenery and numerous hiking trails. Experience the panoramic views of Cape Town and the coastline from the iconic Table Mountain.
  • Chapmans Peak: Renowned for its scenic drive, Chapmans Peak boasts dramatic cliffs and sweeping ocean views. It's an ideal spot for outdoor enthusiasts, offering hiking trails and picturesque picnic spots.

Things to do recommended for couples

For a romantic getaway in Simon's Town, indulge in wine tasting at Steenberg Wine Estate, a mere 5.6km away. Embrace adventure with surfing lessons at Learn 2 Surf, just 4.3km from town, or take in breathtaking views via the Table Mountain Aerial Cableway, located 14.3km away.

Things to do recommended for families

Families visiting Simon's Town can enjoy a delightful day at Woolley's Tidal Pool, located 2.5km away. This outdoor spot offers a fantastic family atmosphere, perfect for swimming and playing, ensuring a fun-filled experience for all ages.

Things to do recommended for groups

Enjoy a round of golf at Simon's Town Country Club, indulge in shopping and entertainment at Longbeach Mall, or immerse yourselves in culture at the Kalk Bay Theatre. These experiences will offer your group a delightful taste of local life in Simon's Town.

What do I need to keep in mind when booking a vacation around Simon's Town

If you're planning a trip with friends, family, or pets, or if you're interested in extended stays, be sure to apply the appropriate filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Simon's Town with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Simon's Town with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Simon's Town: For many, a family holiday isn't quite the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Simon's Town: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Simon's Town

Simon's Town, nestled in the Western Cape of South Africa, offers an idyllic holiday experience with its stunning coastal scenery and relaxed atmosphere. Explore the charming neighbourhood, perfect for families, beach lovers, and those seeking luxury. Nearby, the enchanting Gordon's Bay beckons with its secluded beaches and romantic vibes, making it a perfect escape for travellers. Whether you're seeking adventure or relaxation, Simon's Town and its surroundings promise an unforgettable getaway.

  • Froggy Farm: Located a mere mile from Simon's Town, Froggy Farm offers a delightful blend of outdoor activities and romantic entertainment. Visitors can enjoy a round of golf at the nearby course, or catch a theatrical performance at a local venue. The neighbourhood is also home to beautiful beaches and a fascinating museum, making it a perfect spot for those looking to soak in both nature and culture. The tranquil atmosphere and scenic surroundings make Froggy Farm a lovely retreat for couples and families alike.
  • Glencairn: Just two miles from Simon's Town, Glencairn is a vibrant neighbourhood known for its shopping options and dynamic entertainment scene. The area features a bustling shopping centre, where visitors can explore a variety of shops and enjoy a leisurely day out. Families will appreciate the proximity to the beach and local parks, perfect for picnics and outdoor fun. Glencairn combines the charm of coastal living with modern conveniences, making it an ideal destination for those seeking both relaxation and activity.
  • Kilfinan: Located three miles away from Simon's Town, Kilfinan is a family-friendly neighbourhood that offers a delightful array of outdoor pursuits. Enjoy a visit to the local market or explore the recreational areas designed for family fun. With its beautiful beaches and parks nearby, Kilfinan provides ample opportunities for relaxation and play. This charming area is perfect for families looking to create lasting memories while enjoying the stunning landscapes of the Western Cape.

Best time to go to Simon's Town

If you're planning a trip to Simon's Town, it's a good idea to check both the weather and property rates. The warmest months are January and February. Peak season runs in March and December to January, while off-peak times, like May to June and August tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.7°F (21.5°C)No Rain (Dry)SunnySlightly HighSlightly High
February70.7°F (21.5°C)No Rain (Dry)SunnyAverageSlightly High
March68.5°F (20.3°C)No Rain (Dry)SunnySlightly HighAverage
April64.6°F (18.1°C)No Rain (Dry)SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnySlightly LowSlightly Low
June57.0°F (13.9°C)Light RainMostly SunnySlightly LowSlightly Low
July55.4°F (13.0°C)Light RainMostly SunnyAverageAverage
August55.8°F (13.2°C)Light RainMostly SunnySlightly LowAverage
September57.7°F (14.3°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
October62.1°F (16.7°C)No Rain (Dry)Mostly SunnyAverageAverage
November64.6°F (18.1°C)No Rain (Dry)SunnyAverageAverage
December68.2°F (20.1°C)No Rain (Dry)SunnySlightly HighSlightly High

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a practical platform for you to plan new journeys, resume your previous ones, or manage your travel arrangements. You can easily access the properties you’ve saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Simon'S Town?
Prices for holiday rentals in Simon'S Town vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simon'S Town to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Simon'S Town holiday house rentals?
You can find great discounts on house rentals in Simon'S Town on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Simon'S Town holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Simon'S Town with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Simon'S Town?
A long-stay holiday rental in Simon'S Town is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Simon'S Town for a holiday rental?
The best time to visit Simon's Town for a holiday rental is during the peak season from December to February, with January being particularly popular among travellers. This vibrant summer period invites visitors to explore the stunning coastline, enjoy outdoor activities, and soak up the sun. The warm weather, with temperatures averaging between 20 to 30 degrees Celsius, creates the superb environment for a range of activities, from hiking in the nearby Table Mountain National Park to enjoying the picturesque beaches.

January sees a lively option in Simon's Town, with both locals and tourists flocking to the area to experience its unique charm. Visitors can indulge in delightful seaside dining, engage with friendly locals, and take part in various events and festivals that highlight the region's rich culture.

For those seeking a more budget-friendly option, consider visiting in May, when the crowds thin out and you can still enjoy the beauty of the coast without the busyness of peak season. The autumn backdrop offers a quieter experience, allowing you to appreciate the scenic landscapes at a leisurely pace.
How early should I book a Simon'S Town holiday rental?
Book your Simon'S Town holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Simon'S Town, Western Cape, South Africa?
In Simon's Town, visitors can enjoy a variety of attractions that showcase the area's rich maritime history and stunning natural beauty. The South African Navy Museum offers insights into the naval history of the region, situated conveniently near the picturesque Simon's Town harbour. Holiday rentals in this area typically provide easy access to the charming waterfront, where visitors can find a range of restaurants and shops.

Boulders Beach, famous for its resident African penguin colony, is a must-visit and is just a short drive from the town centre. Here, you can relax on the sandy beach while observing the playful penguins in their natural habitat.

Another highlight is the scenic coastal drive along the Cape Peninsula, which offers breathtaking views and access to hiking trails in the nearby Cape Point Nature Reserve. This reserve is known for its diverse flora and fauna, as well as the iconic lighthouse at Cape Point, making it a popular spot for those seeking outdoor adventures.
Can I change or cancel my Simon'S Town home rental booking on Vrbo?
To find Simon'S Town holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Simon'S Town holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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