Holiday houses in Simon's Town

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Top-rated holiday rentals in Simon's Town

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Villa in Simon's Town

4.93 out of 5 average rating, 195 reviews

Whalesong by Steadfast Collection

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!

Top Guest favourite

Apartment in Simon's Town

4.92 out of 5 average rating, 228 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.

Guest favourite

Villa in Simon's Town

4.89 out of 5 average rating, 218 reviews

Cape Point Mountain Getaway - Villa

A magnificent historical home surrounded by fynbos, overlooking False Bay with stunning sea views and an imposing mountain backdrop. The villa is located in a nature conservancy. It is completely off the grid: solar energy, water from a mountain stream. This place is for people who want beauty and tranquillity and a getaway experience in a 100% environmentally friendly place right on the urban edge - 8kms from Simonstown. Fully equipped open plan kitchen, exquisite bedrooms and awesome decks.

Guest favourite

Apartment in Glencairn

4.98 out of 5 average rating, 119 reviews

"Seaside Serenity : Ocean Views, Relaxing Retreat"

Escape to our modern self-catering apartment with direct ocean views, a serene atmosphere, meticulous cleanliness, and ample natural light which create the perfect soothing retreat. Take a leisurely 15-minute stroll to unwind on Glencairn Beach or explore the eclectic charm of Kalk Bay with its bohemian vibes and abundant dining and shopping options. Immerse yourself in Simons Town's rich history at the Naval Museum and Arts and Crafts stores. Don't miss the adorable penguins at Boulders Beach.

Top Guest favourite

Home in Glencairn

4.94 out of 5 average rating, 180 reviews

Modern home with breathtaking ocean views

Nestled in the exclusive area of Cairnside, this semi-detached house offers the perfect place to enjoy beautiful views of False Bay and is less than 5 mins from the local beach and tidal pool. One of our favourite past times is watching the water activities from the sheltered deck. Whale spotting, kite surfers jumping in the bay, sailing regattas and flocks of birds migrating along the coast. The sun rises across this side of the bay, if you're up early you'll be mesmerised by the view.

Guest favourite

Cottage in Simon's Town

4.92 out of 5 average rating, 154 reviews

The Lookout at Froggy Farm

Just a few minutes walk from the beautiful False Bay beaches, The Lookout is a mezzanine level house with breathtaking views sitting in a quiet part of Simon's Town. Next to and with access to the iconic Froggy Farm, it is just the place for a relaxing stay away from the crowds. With a dedicated work area and 100mbps fibre, it is also perfect for escaping the city yet remaining connected for a peaceful remote working experience. Ideally suited for couples or families with children.

Guest favourite

Loft in Simon's Town

4.86 out of 5 average rating, 295 reviews

Breathtaking Mountain & Ocean views in Simons Town

The Loft is situated in Simons Town on the Cape Peninsula, an area of incredible natural beauty & gateway to the Marine Big 5. This spacious loft apartment offers beautiful light accommodation with folding doors leading onto a large private balcony & spectacular views of False Bay. The loft includes an open plan bedroom area, sitting room, fitted kitchen & separate bathroom. Private entrance & parking & is only 5 minutes walk to Simons Town amenities, harbour & beaches close by.

Top Guest favourite

Apartment in Hout Bay

4.93 out of 5 average rating, 396 reviews

Endless Views & Privacy

Our studio apartment opens up onto a 40sq meter balcony with a panoramic view of the Hout Bay Valley and the Helderberg mountains beyond. Large sliding doors disappear into the walls creating an unimpeded indoor/outdoor flow while the elevated position protects your privacy. The open plan bathroom faces onto an enclosed secret garden which includes a frame-less glass shower. The unit has a fully equipped kitchenette and is serviced daily except weekends and public holidays.

Guest favourite

Home in Simon's Town

4.84 out of 5 average rating, 134 reviews

Seaview Cottage. Walk to Beach and Penguins

This 3 bedroomed, all ensuite, home is located a short 5 minute walk to Windmill Beach. Windmill Beach was recently voted by as one of the top 10 beaches in Cape Town. You can walk a short distance to see the penguins at Boulders Beach. This home is perfect for those who are looking for tranquility but still centrally located for exploring the South Peninsula. This home perfect for the Cape Town staycationers and loved by local and international travellers.

Top Guest favourite

Apartment in Glencairn

4.96 out of 5 average rating, 452 reviews

(1 ) Sun Sea Sleep - Simon's Town, Cape Town

ONLY TWO PEOPLE ALLOWED. Private self-catering apartment with one bedroom and on suite bathroom, open plan lounge, kitchen and dining area. Fridge/freezer, induction stove and microwave oven. Complementary shampoo, body lotion, coffee, tea sugar and biscuits. Own Patio. We are situated in picturesque Simon's town, home of the SA navy, 10 minutes drive from the famous Boulders beach, where the African Penguins swim among bathers in the sheltered beach.

Top Guest favourite

Apartment in Simon's Town

4.88 out of 5 average rating, 312 reviews

Swim (and walk) with the penguins

Walk to safe swimming beaches and to the penguins in 3 minutes, or wander into historic Simonstown village. Our guest suite is small (6m X 2m), but offers everything you need, plus a view of the sea: wi-fi, a comfortable double bed, the means to make breakfast, place to eat or check emails – and privacy from the main house. It has a separate entrance and a private bathroom. A small garden for your exclusive use offers a table, chairs and Weber.

Guest favourite

Home in Simon's Town

4.81 out of 5 average rating, 242 reviews

Beautiful home, fantastic sea views in Simonstown

Light and airy, spacious, Christian-owned home. Large and sheltered sun deck with sweeping views of the ocean and surrounding mountains. Walking distance to the village and a choice of beaches. If you are looking for a beautiful and quiet place to relax, refresh and renew, then this is the home for you! Regret no parties or excessive drinking. No smoking. Noize needs to be controlled as it is a quiet neighbourhood with permanent residents.