Discover a selection of 63 vacation rentals in Simon's Town, Cape Town that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $41 per night, and houses and cottages are popular options for a stay in Simon's Town. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Simon's Town
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What are the top vacation rentals in or near Simon's Town?

The heart wants what the heart wants, and right now it wants to go on vacation. Now's the time to pack your suitcase and escape to one of these top vacation rentals in or near Simon's Town:

  • Make the most of handy amenities like a fenced yard and a travel crib at Dolphin Cottage With Amazing Views. Situated around 1 mile from Simon's Town, this unique option has 4 bedrooms and is a hit with guests.
  • Another great choice is Cozy Dreamy Cottage With Endless Sea Views, which is around 4 miles from Simon's Town. Offering 3 bedrooms, a free nearby fitness center and heating, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Simon's Town vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Simon's Town?

If you're in need of somewhere to completely switch off for a couple of days, there's no shortage of awesome weekend getaways in and near Simon's Town. Enjoy some downtime at one of these top options:

  • Around 4 miles to the north of Simon's Town, Sea Cottage - 6 Sleeper Holiday Home has everything you need for a short weekend break, including a stovetop and a microwave oven. When you're ready to venture out and explore, there are lots of outdoor attractions to see like Cheetah Outreach and Signal Hill.
  • Another excellent option is Sunset On Mountainrise With Exquisite Sea And Mountain Views, around 4 miles west of Simon's Town. When you're not relaxing in your rental making use of an iron and ironing board and a hair dryer, be sure to visit Helderberg and Clovelly Golf Course.

What are the best romantic weekend getaways in or near Simon's Town?

Forget chocolates and roses. Sometimes all you need is to take off for a weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Simon's Town that would make even old Cupid swoon. Here are some we think you'll adore:

  • Located around 1 mile from Simon's Town, Dolphin Cottage With Amazing Views is an ideal place for doting lovebirds. An ocean view and a nearby bay are just some of the amenities here.
  • Another place where you can spend a few dreamy days together is Cozy Dreamy Cottage With Endless Sea Views. Located around 4 miles from Simon's Town, a dining table and an ocean view add to the atmosphere here.

What's the best place to stay if you're looking to rent a house for a weekend in or near Simon's Town?

A weekend of fresh coastal air and chilled vibes at Boulders Beach in Cape Town will work wonders for your soul. Check in to a rental home and stay a couple of nights at this beautiful stretch of shoreline located 19 miles to the north of Simon's Town.

What are the best large group vacation rentals in or near Simon's Town?

Share your trip and boost your odds of having fun. Whether you're planning an adventurous escape with friends for a family get-together, there's no shortage of large group vacation rentals in and near Simon's Town:

  • There's loads of space to move around at Luxury, Serviced Private Estate. Around 14 miles north of Simon's Town, this expansive retreat has 5 bedrooms accommodating up to 12 guests. Amenities include a private pool and free toiletries.
  • Nothing takes priority over hanging out with loved ones, and Beautiful Villa At The Beach is the perfect place to do that. Located around 14 miles to the northwest of Simon's Town, as many as 12 people can stay in this vacation rental which has 6 bedrooms. Outdoor furniture and a porch are among the many amenities here.

What are the best houses for rent with a pool in or near Simon's Town?

Nothing screams good times like a pool does. Pull out your inflatable flamingo and browse these houses in or near Simon's Town that feature this added perk:

  • Make yourself comfortable at Stylish, Comfortable, Perfectly Located House With Heated Pool And Mountain Views, where your highest priority will be enjoying the pool. Amenities including a toaster and shopping help make this retreat a favorite with guests.
  • Alternatively, enjoy a more leisurely pace of life at Stunning 5 Bedroom, 5 Bathroom Camps Bay House. Along with a refreshing pool, you can also make use of a separate dining area and a stovetop.

Don't know how to pack your suitcase for your Simon's Town escape? This enticing destination has a mediterranean climate. In summer, you can expect average temperatures ranging from 65 ºF to 80 ºF. Check out our selection of Simon's Town vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Simon's Town?

You'll always have more fun sharing those precious memories with the ones that are closest to your heart. Whether you're planning a family catch-up or taking time out with friends, Vrbo has a large vacation rental that's just right for you. Here are two of our best in and around Simon's Town:

  • About 1 mile to the west of Simon's Town, Dolphin Cottage With Amazing Views has 4 bedrooms and sleeps up to 8 guests. It's equipped with a range of amenities, including an oven and a fireplace.
  • Newly Refurnished Fantastic Views From Panorama Terrace Borehole Water also offers the space you need to share special moments with loved ones. This rental is around 12 miles to the northwest of central Simon's Town and accommodates as many as 8 guests in its 4 bedrooms. A dining table and a porch will help keep everyone happy and comfortable.

If you want to see some family-friendly attractions around the area, there's no shortage of choice. Two Oceans Aquarium, Sea Point Swimming Pool and Cape Town Film Studios offer fun for all the crew.

Can I find two-bedroom vacation rentals in or near Simon's Town?

Absolutely. From modern apartments to comfy cabin retreats, Vrbo offers a selection of rentals. Traveling families will adore these two-bedroom beauties in or near Simon's Town:

  • With amenities like a TV and a nearby beach, Lovely 2 Bedroom Self Catering Apartment With Beautiful Sea View has all you need for an excellent stay. Settle in and then get out and explore your surrounds.
  • Sunrise Sea Villa - Simonstown is another popular two-bedroom property in the Simon's Town area. It provides convenient amenities like towels and a private pool.

Are there vacation rentals with fire pits in or near Simon's Town?

Whether you want to share a bottle of wine beside the flames with your sweetheart or simply stay toasty after the sun sets, we'll help you find a vacation rental with a fire pit. Here are two of our favorite options in or near Simon's Town:

  • Laugh, sing and reconnect with old and new friends around the fire at Newly Refurnished Fantastic Views From Panorama Terrace Borehole Water. This escape offers lots of other great amenities, such as a nearby laundromat and a hair dryer.
  • Holiday Home With 2 Bedrooms, Big Veranda is another place where you can toast marshmallows around an open fire. It also features off-street parking options and air conditioning.