A coastal town with a marina, boats, and a beach.

Simon's Town vacation rentals

We found 125 vacation rentals — enter your dates for availability

Experience the breathtaking beauty of Simon's Town, where stunning beaches meet scenic capes and vibrant neighborhoods come alive with local culture. This idyllic destination offers an array of family-friendly activities, from swimming alongside playful African penguins at Boulders Beach to hiking the dramatic trails of Chapmans Peak. Choose from luxurious villas or cozy apartments that provide ample space and amenities, ensuring your group enjoys a true home-away-from-home experience in this coastal paradise.

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Find properties near top attractions in Simon's Town

A rocky beach with large boulders, clear turquoise water, and a few penguins on the shore.

Boulders Beach

A beach with penguins and rocky outcrops in the water.

Foxy Beach

Find the best place to stay - Simon's Town

PingusHouse Villa with private Swimming Pool And Garden In Simon's Town

Sleeps 8 · 4 bedrooms · 1 bathroom

Winford Manor offers the ultimate seaside escape.

Sleeps 2 · 1 bedroom · 1 bathroom

Views, Beaches, Barbeques and more at Tom's Cabin: 3 Bedrooms, Sleeps 6

Sleeps 6 · 3 bedrooms · 2 bathrooms

Private Oceanview Villa: Plunge Pool, Braai, Walk to Penguins, False Bay

Sleeps 4 · 2 bedrooms · 2 bathrooms

Glorious weather in Cape Town rn! Hot tub, Sea Views, secure parking, nr beach

Sleeps 6 · 3 bedrooms · 3 bathrooms

Rocky Beach Self Catering Home Simon's Town. Panoramic sea views of False Bay.

Sleeps 6 · 3 bedrooms · 1+ bathroom

Top rated rentals - Simon's Town

Image of Lark House, Peaceful Mountain Home with Amazing Ocean Views

Great owner to work with

Visiting from the USA to see family and to check off a bucket list item. Owner was great. Late flight and they let our family pick up the key so we wpuldnt have to bother them so laye. Power went out and back up did not switch on. They brought flashlights dow and took the ols ones back to recharge. Beautiful place and of we ever go back would definitely book here again. Only downfall if the driveway but we figured it out.

Lisa W.

Stayed Nov 2024

Positively Charming Holiday Stay

My husband and I spent 4 lovely nights in this charming cottage overlooking False Bay, in Simon’s Town, Cape Town, South Africa. It had everything we needed and the local manager who checked us in was fantastic and provided lots of recommendations for places to go, sites to see, and where to eat. We enjoyed walking down to the beach to see penguins and other wildlife. We were even once greeted by a baboon calling out from the top of a house nearby. The view is breathtaking! You can see the sunrise over the bay in the morning as you drink your coffee on the portico or from the seating area inside. The owner has numerous potted plants as well as grape vines adorning the entrance way and outdoor seating areas. There is a beautiful mosaic mermaid mural which represents the naming of the cottage. Communication before and during the stay was with both the owner and the manager was excellent. We would love to stay here again in the future. A few days here left us wanting more.

KarenBeth B.

Stayed Sep 2024

Image of Whalehaven: Kalk Bay apt, spectacular sea and harbour views

Wonderful apartment close to train station

Apartment was spacious and comfortable. Even though it was on the main road, the noise didn’t bother us all that much. Louise, who manages the apartment along with her husband was gracious and met us when we arrived, even though we were a bit late. She gave some great recommendations for restaurants in the area. Room and bed was comfortable with a wood-burning stove to heat the apartment. One possible discrepancy we noted is that the listing says that the apartment has a dryer, but we were unable to find it. However, there was a drying rack and washing machine. Overall, a very nice place to stay for a few nights Nice view out over the ocean.

Edward H.

Stayed Jul 2024

Image of Luxury Villa is situated in the heart of Kalk Bay, on the warm False Bay coast.

PERFECT Family retreat

We stayed over a week at the Bishop View House after several weeks camping in Kruger. We are an active family of 7 ranging in age from 70 to 4. Bishop View is a luxurious, very safe (sophisticated alarm system) and centrally located home. We cooked most of our meals and found the kitchen well equiped, the sauna/steam room was wonderful, and the quick dip in the pool afterwards was spa-quality luxury! Any question we had was quickly answered and support staff were superb. The location is within easy walking distance of soaking tide pools, fun shops, great restaurants, hikes up the hills behind the house, and even a wonderful beginner surfing beach! We recommend Bishop View house without reservation!

Susan S.

Stayed Apr 2024

Image of Luxury apartment with exquisite harbour views

The perfect place to say in Kalk Bay

This is an exceptional VRBO and we have stayed in many around the world and own 2 in the FL Keys. From the beginning correspondence with the owner, 2 months before our arrival, to the morning we left it was perfect. Before booking, Zelda was so helpful in answering all of my questions up front to make sure we chose the perfect spot that fit our 70 year old needs. We wanted to be able to walk to restaurants & town without climbing several blocks to get home. The check in staff were prompt and friendly to help with the internet, heaters and even got my phone working on whatsapp,which is not in their job description, but when asked they just jumped in with their young brains and helped this old lady figure it out. The guards at the gate were kind and always friendly. We highly recommend Kalk Bay in general, but this place fit the bill for us because the lovely Bootlegger restaurant right in front allowed us to get coffee and breakfast in the morning with zero hassles. I highly recommend the Olympian just a block away for a superb dinner and a sweet little wine beer shop is only a few doors away. So basically you can walk to whatever is needed from this apartment and feel safe any time day or night. I wish we could come back soon, but alas this was our Africa trip of a lifetime.

Shelly M.

Stayed Sep 2023

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Find out more about Simon's Town

Why visit Simon's Town

Beautiful Beaches: Enjoy stunning coastal views and relax on the serene beaches, perfect for sunbathing and water activities.
Rich History: Discover local heritage at museums and historic sites that showcase Simon's Town's fascinating past.
Outdoor Adventures: Engage in various outdoor activities, from hiking to water sports, set against breathtaking landscapes.
Charming Neighborhoods: Explore quaint streets filled with shops, cafes, and local art, reflecting the town's unique culture.
Family-Friendly Attractions: Experience a range of activities suitable for all ages, making it an ideal vacation spot for families.

Popular types of accommodation around Simon's Town

Vrbo offers a variety of vacation rentals in Simon's Town, perfect for any traveler. Whether you're looking for cozy apartments, spacious houses, or luxurious villas, you'll find the ideal spot for your getaway. Popular options include charming holiday cottages and comfortable flats to rent, accommodating families or groups in stylish bedroom homes. Discover your perfect Simon's Town retreat today.

Apartments: The top choice for vacation rentals in Simon's Town, offering a comfortable and convenient home away from home.
Houses: Ideal for families or groups, these homes provide spacious living areas and a personal touch.
Villas: Luxurious accommodations with stunning views, perfect for an upscale getaway.
Cottages: Quaint and cozy, these rentals create an inviting atmosphere for a relaxing stay.
Condos: Modern amenities and shared facilities make condos a practical option for travelers.**

Top attractions in and around Simon's Town

Simon's Town is a fantastic destination for outdoor and family vacations, offering a mix of beautiful beaches, rich history, and cultural experiences. Visitors can explore stunning coastal landscapes, delve into local history at museums, and enjoy various outdoor activities. Whether you're traveling with family or friends, Simon's Town provides the perfect backdrop for an unforgettable getaway in Cape Town, Western Cape, South Africa.

Boulders Beach: Famous for its unique colonies of African penguins, Boulders Beach offers stunning coastal views and sandy shores, perfect for sunbathing and swimming while enjoying the playful antics of the penguins.
Table Mountain National Park: This breathtaking national park provides outdoor adventures such as hiking and rock climbing, along with picturesque scenery that includes stunning views of the ocean and Cape Town from the iconic Table Mountain.
Simon's Town Museum: Immerse yourself in the rich maritime history and culture of Simon's Town at this museum, which showcases artifacts, photographs, and exhibits that tell the story of the town's past.

Things to do recommended for couples

For a romantic getaway in Simon's Town, indulge in wine tasting at Steenberg Vineyards, just 8 miles away. Embrace adventure with surfing lessons at Learn 2 Surf, 7 miles from town. Don't miss breathtaking views from the Table Mountain Aerial Cableway, located 17 miles away.

Things to do recommended for families

Your family will love Woolley's Tidal Pool, just 4 miles from Simon's Town. This spot offers a fun outdoor vibe perfect for kids, with plenty of opportunities for swimming and exploring the natural beauty of the area.

Things to do recommended for groups

Enjoy a round of golf at Simon's Town Country Club, shop and unwind at Longbeach Mall, or catch a captivating performance at Kalk Bay Theatre. These activities offer a perfect blend of outdoor fun, shopping, and cultural experiences for your group in Simon's Town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When you're planning a trip—whether with friends, family, your pets, or for an extended stay—it's important to focus on what matters most to you. Here are some helpful Vrbo booking tips to guide you.

Traveling to Simon's Town with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search on Vrbo to include all of these options and more.
Traveling to Simon's Town with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
Taking your pets with you to Simon's Town: For many families, a vacation isn't truly complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
Planning for a long term stay visiting Simon's Town: If you're in search of vacation rentals that offer discounts for month-long stays, 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Simon's Town

Simon's Town, nestled along the stunning coast of Cape Town, offers a delightful mix of outdoor adventures and family-friendly attractions. Explore its charming neighborhoods, indulge in luxury experiences, and soak in breathtaking sea views. Whether you're seeking a romantic getaway or a relaxing retreat, the area's secluded beaches and vibrant atmosphere make it a perfect destination. Don’t miss the chance to discover the coolest spots around Simon's Town for an unforgettable vacation experience.

Cape Town: Cape Town is a vibrant metropolis that serves as the gateway to Simon's Town. Known for its stunning natural beauty, this city offers a wealth of outdoor activities, making it a popular destination for families and business travelers alike. From picturesque beaches to world-class golf courses, Cape Town boasts an array of attractions. Don't miss the iconic Table Mountain, where you can hike or take a cable car for breathtaking views. The bustling V&A Waterfront is perfect for shopping, dining, and entertainment, ensuring a memorable experience for every visitor.
Froggy Farm: Located just a mile from Simon's Town, Froggy Farm is a charming neighborhood that promises a delightful escape. Known for its romantic ambiance and outdoor activities, this area is ideal for couples seeking a quiet getaway. Explore the local historic sites and visit the nearby museum to delve into the region's rich history. With access to beautiful beaches and a peaceful environment, Froggy Farm offers an idyllic setting for picnics, walks, or a round of golf at the nearby country club.
Glencairn: Situated two miles away from Simon's Town, Glencairn is a picturesque neighborhood that combines outdoor fun with business-friendly amenities. This area features a variety of shopping options, from local boutiques to larger shopping centers, catering to all your retail needs. Glencairn is also home to beautiful family beaches and parks, making it a great spot for relaxation and recreation. Whether you're looking to shop, dine, or unwind by the seaside, Glencairn has something for everyone.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.7°F (21.5°C)	No Rain (Dry)	Sunny	Slightly High	Slightly High
February	70.7°F (21.5°C)	No Rain (Dry)	Sunny	Average	Slightly High
March	68.5°F (20.3°C)	No Rain (Dry)	Sunny	Slightly High	Average
April	64.6°F (18.1°C)	No Rain (Dry)	Sunny	Average	Average
May	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
June	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
July	55.4°F (13.0°C)	Light Rain	Mostly Sunny	Average	Average
August	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
September	57.7°F (14.3°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly Low
October	62.1°F (16.7°C)	No Rain (Dry)	Mostly Sunny	Average	Average
November	64.6°F (18.1°C)	No Rain (Dry)	Sunny	Average	Average
December	68.2°F (20.1°C)	No Rain (Dry)	Sunny	Slightly High	Slightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can be beneficial since prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you stopped, or review and organize your travel arrangements all in one place. Your saved or booked properties will be neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Simon'S Town?

In Simon's Town, apartments are the most common vacation rental option, with about 20 available throughout the area. These apartments are typically situated near the picturesque coastline and offer amenities such as fully equipped kitchens, cozy living spaces, and often balconies or patios with stunning views of the ocean. For those seeking a bit more space, there are around 10 vacation houses available, which usually include multiple bedrooms and private outdoor areas, great for families or groups. Additionally, several villas, cottages, and condos provide a variety of styles and settings for travelers.

Are there any beach house rentals in Simon'S Town?

In Simon's Town, there are around 67 beach house rentals available, making it a great destination for those seeking a coastal getaway. These rentals are typically situated near the picturesque waterfront and offer stunning views of the ocean. Many beach houses come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios ideal for enjoying the sea breeze.

How much does it cost to rent a vacation home in Simon'S Town?

Prices for vacation 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 vacation 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.

What are popular rental amenities in Simon'S Town?

In Simon's Town, popular rental amenities include decks or patios, fully equipped kitchens, and balconies that provide stunning views of the surrounding scenery. Many properties also feature patios where guests can relax outdoors and enjoy the pleasant climate. Additionally, the proximity to the sea is a noteworthy aspect, with several rentals located just a short walk from the coastline, allowing travelers to easily access the beautiful beaches and waterfront activities.

Can I find family house rentals in Simon'S Town?

In Simon's Town, you can find a variety of family-friendly vacation rentals, with around 12 options available. This picturesque coastal town, known for its stunning beaches and historical significance, offers accommodations that cater to families perfectly. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play or enjoy the beautiful views.Visitors can explore nearby attractions, such as the famous Boulders Beach, home to a colony of African penguins, and the scenic hiking trails of the Cape Peninsula. Additionally, the charming local shops and restaurants contribute to a friendly setting for families.

Can I rent a vacation home with a pool or hot tub in Simon'S Town?

In Simon's Town, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 12 properties boasting private pools and several others offering hot tubs. This picturesque coastal town, known for its stunning views of False Bay and the nearby Boulders Beach, is an excellent destination for relaxation and outdoor activities.Many of these rentals come equipped with desirable amenities, such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them superb for family gatherings or group vacations. Additionally, some properties might include features like barbecue facilities, gardens, and quick access to the beach, enhancing the overall experience. Find your rental in Simon'S Town with a pool or a hot tub.

Are there any Simon'S Town vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Simon'S Town with parking available—perfect for families or travelers 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 book pet-friendly vacation rentals in Simon'S Town?

In Simon's Town, travelers can find several pet-friendly vacation rentals that cater to those looking to enjoy a coastal getaway with their furry companions. Many of these rentals offer stunning views of the ocean and the surrounding mountains, with amenities such as spacious living areas, outdoor patios, and fully equipped kitchens, great for preparing meals after a day of exploring.The area is known for its beautiful beaches, including Boulders Beach, where visitors can enjoy the famous colony of African penguins. This beach is a fantastic spot for walks with pets, allowing for a memorable experience by the sea. Additionally, the nearby Simon's Town waterfront features charming shops and restaurants, providing a lovely atmosphere for leisurely strolls. See all pet-friendly rentals in Simon'S Town.

Can I find long-stay vacation rentals in Simon'S Town?

A long-stay vacation rental in Simon'S Town is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.

When is the best time to visit Simon'S Town for a vacation rental?

The best time to visit Simon's Town for a vacation rental is during the peak season from December to February, with January being particularly popular. This summer period is ideal for travelers seeking warm weather and vibrant outdoor activities, as temperatures typically range from the mid-60s to mid-80s Fahrenheit. Visitors can enjoy picturesque beaches, whale watching, and exploring the scenic coastline, all while soaking in the lively option that this charming town offers.January brings a bustling energy, with both locals and tourists reveling in the sunshine. It's a fantastic time for travelers, as you can easily partake in water sports, hike in the nearby Cape Point Nature Reserve, or simply relax by the beach. The combination of pleasant weather and diverse activities makes it an attractive choice for those looking to create memorable experiences.If you're considering a more budget-friendly option, May is a wonderful time to explore Simon's Town. Although it falls in the low season, the weather remains mild, and you can experience a more tranquil ambiance while enjoying the stunning scenery and local attractions without the crowds. This month is great for those looking to appreciate the beauty of the area at a more leisurely pace.

Are there any remote work vacation rentals in Simon'S Town?

In Simon's Town, there are several remote work vacation rentals available, with around 23 options to choose from. This charming coastal town, located on the Cape Peninsula, is not only known for its picturesque scenery but also offers suitable amenities for those working remotely. Many rentals feature free Wi-Fi, both in private rooms and common areas, allowing for uninterrupted work sessions while enjoying stunning views of the ocean or the surrounding mountains.Travelers can expect comfortable living spaces, often with dedicated work areas, ensuring a productive environment. Additionally, some properties offer outdoor spaces where guests can take breaks and enjoy the fresh sea air. The proximity to local attractions, such as the famous Boulders Beach with its resident penguin colony and the historic Simon's Town waterfront, provides an excellent balance of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

How early should I book a Simon'S Town vacation rental?

Book your Simon'S Town vacation 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 vacation 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 explore a variety of attractions that showcase its rich maritime history and natural beauty. The Boulders Beach, famous for its colony of African penguins, offers a great experience where travelers can view these charming birds up close while enjoying the stunning coastal scenery. Vacation rentals in this area often provide easy access to the beach and picturesque views.The historic Simon's Town itself features the South African Naval Museum and the iconic Just Nuisance statue, a tribute to the Great Dane who was a beloved part of the naval community. Properties in the town center allow guests to immerse themselves in local culture, with quaint shops and eateries just a short stroll away.For outdoor enthusiasts, the nearby Cape Point Nature Reserve presents breathtaking landscapes and hiking trails, where visitors can enjoy panoramic views of the ocean and rugged cliffs.

Can I change or cancel my Simon'S Town home rental booking on Vrbo?

To find Simon'S Town vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, 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 organizing 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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