
Holiday rentals in Simon's Town
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Simon's Town
Guests agree: these stays are highly rated for location, cleanliness and more.

The Lookout - dream, hide, explore!
Calling all explorers, dreamers and creatives! Come for a quick retreat or stay to write that book. The lookout was built by owner Rob himself over ten years. There is thought and love behind every little detail. The house isn't perfect, there is raw wood, some things aren't finished, the furniture is vintage and may appear worn but if you look past that, you will find that everything there has its own story and that this house is made for the big things: sunrises, ocean dreaming and full-moons

Perfect holiday location with stunning sea views
Holiday home outside Simonstown on the Cape Peninsula, close to the "penguin beach". Sleeps four in two bedrooms. Open plan kitchen/lounge flows onto a large deck with expansive sea views. Two full bathrooms (main en-suite). Within easy reach of Cape Point Reserve, and the delightful shops & restaurants of Simonstown, Kalk Bay & Muizenberg. Walking distance to swimming spots. Tasteful decor with modern appliances, a smart Google TV and pure cotton linen on the beds. Minimum stay is two nights.

Cape Point Mountain Getaway - Cottage
This is one of Cape Town's environmental and historic treasures. It is a candle-lit hideaway with stunning views of mountain and sea. The Cottage is completely off grid, with fresh water coming off the mountain and energy from the sun. The cottage is built from local materials - stone walls, reed ceilings, blue gum supports. There are glass doors and windows throughout the cottage. The cottage has a beautiful open-plan bedroom and bathroom. The bathroom includes a tub, a toilet and a basin.

Plumbago Cottage
A beautiful , separate entrance flatlet with magnificent views of the ocean over False Bay. Spacious, light and stylish , with quirky touches to make you feel at home. Situated within walking distance of beautiful beaches .We are a 10 minute walk to the Boulders Beach penguin colony and 20 minutes walk from restaurants and historical sites in Simon's Town .The flatlet is attached to our home yet totally private with own entrance via a pathway flanked by plumbago and views of the mountain.

WhaleDance
Our home is on the Historical Mile with panoramic views, just one block up from the Main Road and near all the cafes and eateries Simon's Town offers. Boulders Beach and the famous penguins are an easy 20 minute walk away and Long Beach is 10 minutes away as is the railway station. This is a high quality accommodation, All three bedrooms are en-suite, with spacious and sound-proofed rooms. A well equipped kitchen with an outside deck with South African 'Braai', pool and seating area.

Private poolside luxury studio with sea view
Wake up in Blue Skies Studio and look across your private swimming pool to see the sun rise over the ocean. This 72 square meter studio with its outdoor lifestyle has private access, parking on the property and excellent security. It is in the mountains, sheltered from the wind and walking distance from Boulders Beach and the penguins. There's lots to do, but you may not want to leave. It is a perfect haven for a short escape, longer-term retreat or the ideal “Work-from-Home” location.

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.

The Sky Cabin Misty Cliffs
Experience one of the most pristine stretches of the south peninsula coastline from our laidback house. The upstairs offers spectacular ocean views with a big open plan bathroom. Downstairs is the perfect setting for dinners around the dining table leading onto the open plan kitchen. The downstairs double bedrooms share a bathroom and the front bedroom has beautiful sea views. While the downstairs deck is great for sundowners. Situated 45 minutes from Cape Town’s city centre.

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.

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.

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 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.

180• Sea Views from a Hillside Villa, Solar Power
180 degree fantastic view of False bay Guests have access to all area's of the house If a guest needs any help or information I am there to assist The house is in a quiet, safe, and beautiful area surrounded by beaches. Penguin Beach is five minutes away, and the excellent Lighthouse restaurant in Simonstown is a must-do. Trendy Kalk Bay is a 10-minute drive, and has shops and restaurants. The train is a 10minute walk
Popular amenities for Simon's Town holiday rentals
Other great holiday rentals in Simon's Town

Seaforth Seaview Cottage, steps from the beach

Top Rated ”The Whalespotter on the sea”

Scenic Blue Studio

Ragamuffin Rest

Charming seaside house near penguin reserve

Serenity

Shamayim Katan (Little Heaven)

Chic Heritage Hideaway near the penguins
When is the best time to visit Simon's Town?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $119 SGD | $105 SGD | $106 SGD | $106 SGD | $100 SGD | $90 SGD | $92 SGD | $97 SGD | $96 SGD | $110 SGD | $112 SGD | $149 SGD |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
Quick stats about holiday rentals in Simon's Town

Total holiday rentals
Explore 460 holiday rentals in Simon's Town

Nightly prices starting at
Simon's Town holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 15,200 verified reviews to help you choose

Family-friendly holiday rentals
250 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
100 properties feature pools

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wifi availability
440 of Simon's Town holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Simon's Town rentals

4.8 Average rating
Simon's Town stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Smoking-friendly rentals Simon's Town
- Rentals with breakfast Simon's Town
- Rentals with a patio Simon's Town
- Rentals with a washing machine and dryer Simon's Town
- Private suite rentals Simon's Town
- Guest house rentals Simon's Town
- Beachfront rentals Simon's Town
- House rentals Simon's Town
- Rentals with pools Simon's Town
- Rentals with a fireplace Simon's Town
- Waterfront rentals Simon's Town
- Pet-friendly rentals Simon's Town
- Villa rentals Simon's Town
- Rentals with beach access Simon's Town
- Flat rentals Simon's Town
- Rentals with a firepit Simon's Town
- Bed and breakfasts Simon's Town
- Apartment rentals Simon's Town
- Family-friendly rentals Simon's Town
- Fitness-friendly rentals Simon's Town
- Rentals with a beach view Simon's Town
- Rentals with outdoor seating Simon's Town
- Bo-Kaap Museum
- Cbd
- Cape Town International Convention Centre
- Atlantic Seaboard Community
- Cape Town Stadium
- Fish Hoek Beach
- Bloubergstrand Beach
- V & A Waterfront
- Muizenberg Beach
- Boulders Beach
- GrandWest Casino and Entertainment World
- Long Beach
- Canal Walk Shopping Centre
- Green Point Park
- Clifton 4th
- St James Beach
- Hout Bay Beach
- Stellenbosch University
- Babylonstoren
- District Six Museum
- Tyger Waterfront Apartments Deck
- Noordhoek Beach
- Jonkershoek Nature Reserve
- Two Oceans Aquarium




