Vacation rentals in Simon's Town

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simon's Town

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Villa in Cape Town

4.94 out of 5 average rating, 172 reviews

Watch Penguins in the Garden of a Luxury Villa in Boulders

Dine al fresco on the covered deck and marvel at the incredible views over False Bay and an award-winning garden, in which 40 penguins live! This villa has been beautifully decorated by a top designer and all paintings are by the former resident artist. Enjoy the warmer clear water of the best secret beach below the house. House comes with full time staff. The most relaxing, safe and private holiday house. Ultra fast unlimited Wi-Fi and well kitted out with high quality everything - can stylishly host 16 for lunch. Cool in summer and warm in winter - it is the best place in the world! This is a very special holiday house indeed. It is blissfully quiet and private yet easily accessible. Great in winter too. One road back from the sea which is actually an advantage at Boulders Beach as it is hidden away from the many tourists. 100% 5-star reviews - a perfect Airbnb score. The view is unbelievable - bring your binoculars for whale and bird watching. The house has 2 bedrooms and 2 bathrooms and so does the cottage. The large award-winning garden was planted by Kirstenbosch botanical gardens' landscapers 30 years ago. Around 40 penguins live in the garden, which makes it one of the only houses in Africa that can boast that! Lottings the marvellous house manager / keeper is always on hand to help with anything and everything. There is also a games room with a table tennis table. Whale Song is an entertainer's paradise, fully equipped with everything you could hope for and high-end kitchen equipment etc. It is also a modest distance (40km) from Cape Tow, so invite friends to join you for a day or a night. Good old Bose surround sound Hifi with an aux cable so you can play your own music easily. Very quiet - no sign of a neighbour or a tourist. Close proximity to hotspots on the peninsular, including top restaurants and wine estates. Also suitable for corporate strategy getaways, teambuilding, photo / video shoots and experiential showcase meals and events. The house is super safe. has non intrusive CCTV and as it is next to a naval base with armed guards at entry to base over the rd from the house. There are two good new bicycles for you to borrow, as well as a blow up boat and some snorkelling and other beach gear. You won't ever want to leave - this is paradise on earth and is the most relaxing holiday house around. Entire place is yours. Access from the main rd and also a pedestrian gate with a code to Gay rd below. I'm always available to give advice or help with anything at all. Whale Song is a villa in Simon’s Town, a historic and increasingly trendy town. It has lovely restaurants, antique shops, and a great yacht club. Cape Point, endless hiking trails, SCUBA diving and swimming beaches are very close by. Rent kayaks and SUPs and enjoy the clear water and its rich marine life. Or just take it easy and relax before the wonderful view and many birds in the garden. The large patio is sheltered from the wind and is the best venue for hosting long sun drenched lunches! A car is handy but the house is serviced by main bus routes and is a 20 minute walk from the train station - it is then one hour by train (half of it along the coast) to the centre of Cape Town. The house is called Whale Song but it just as well might be named Penguin Song - we love the sound of the birds but be prepared to hear then chattering away till 10 at night and again from 7 in the morning in the garden!

Sep 4 – 11

R8,085 ZAR per night
Guest favorite

Apartment in Simons Town

4.91 out of 5 average rating, 132 reviews

Unbelievable Sea Views from balcony in Simonstown!

Views, Views, Views is what this beautiful, comfortable apartment offers. The uninterrupted sunrise views are out of this world! Fully equipped, spacious, light & bright. Being high up, this holiday apartment gives a feeling of space. The balcony is enclosed with a glass sliding door, so you can sit and enjoy the view irrespective of the weather. Close enough to beaches, restaurants, shops, harbor, penguins, hikes, tidal pools, Cape Point, Kalk bay, Muizenberg-surfers corner and so much more.

Sep 21 – 28

R902 ZAR per night
Guest favorite

Apartment in Cape Town

5.0 out of 5 average rating, 211 reviews

Stylish apartment near the beach

Located 3 minutes walk from the beach, this light, bright and airy 1 bedroom apartment is the perfect blend of ocean side bliss and upmarket luxury. Featuring a patio leading onto an expansive sundeck, sliding doors in the living area and large bay windows in the bedroom, the apartment is flooded with natural light and fresh air. Paired with the neutral aesthetic, open plan living area, tasteful finishes and convenient appliances, settling into your beach side holiday is easy when staying here.

Jun 30 – Jul 7

R1,370 ZAR per night

Popular amenities for Simon's Town vacation rentals

Stay near Simon's Town's top sights

Harbour Bay Mall38 locals recommend
Dixies Restaurant & Bar79 locals recommend
Bertha's Restaurant36 locals recommend
The Salty Sea Dog64 locals recommend
The Lighthouse Cafe68 locals recommend
Fran's Place6 locals recommend

Other great vacation rentals in Simon's Town

Superhost

Home in Cape Town

4.91 out of 5 average rating, 115 reviews

Exclusive Tree House Hideaway

R6,536 ZAR per night
Guest favorite

Guest suite in Simon's Town

4.89 out of 5 average rating, 159 reviews

Boulders Beach,Honeymoon suite, Panoramic Sea View

R2,600 ZAR per night
Guest favorite

Apartment in Cape Town

4.93 out of 5 average rating, 95 reviews

Dream View Studio

Aug 26 – Sep 2

R1,426 ZAR per night
Guest favorite

Vacation home in Cape Town

4.98 out of 5 average rating, 97 reviews

Hidden gem. Views over False Bay. Solar inverter

Aug 1 – 8

R2,287 ZAR per night
Guest favorite

Home in Simons Town

4.81 out of 5 average rating, 85 reviews

Seaview Cottage. Walk to Beach and Penguins

Sep 20 – 27

R2,748 ZAR per night
Guest favorite

Home in Cape Town

4.94 out of 5 average rating, 33 reviews

Stunning Simons Town Ocean View Cottage w Inverter

Mar 6 – 13

R1,936 ZAR per night
Guest favorite

Villa in Simons Town

4.95 out of 5 average rating, 19 reviews

Broadlands Villa

Jun 13 – 20

R2,449 ZAR per night
Guest favorite

Cottage in Simons Town

4.93 out of 5 average rating, 85 reviews

The Lookout at Froggy Farm

Jul 31 – Aug 7

R1,318 ZAR per night
Guest favorite

Condo in Cape Town

4.95 out of 5 average rating, 40 reviews

Boulders Beach Lookout Apartment

R2,300 ZAR per night
Guest favorite

Apartment in Simons Town

4.99 out of 5 average rating, 86 reviews

Private poolside luxury studio with sea view

Aug 14 – 21

R2,509 ZAR per night
Guest favorite

Cottage in Cape Town

4.95 out of 5 average rating, 87 reviews

"Westmore" Self-catering Holiday Flat

Jun 30 – Jul 7

R740 ZAR per night
Guest favorite

Guest suite in Cape Town

5.0 out of 5 average rating, 33 reviews

Your best dose of Vitamin-Sea!

Aug 19 – 26

R1,923 ZAR per night

Quick stats about vacation rentals in Simon's Town

Total rentals

400 properties

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

230 properties are a good fit for families

Total number of reviews

11K reviews

Nightly prices starting at

R189 ZAR before taxes and fees

Destinations to explore

  1. Airbnb
  2. South Africa
  3. Western Cape
  4. Cape Town
  5. Simon's Town