
Holiday rentals in Simon's Town
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Top-rated holiday rentals in Simon's Town
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FROGGIES - self contained - 2 bedroom - seaview
The accommodation is self-contained and has a stunning sea-view. The main bedroom leads to a patio with full table and chairs. Two single beds in the second bedroom. The lounge has a flat screen TV with Netflix and You Tube. Fully fitted self catering kitchen, with eye-level oven and microwave. Separate private entrance, only 5/10 minutes walk from the beach and close to the penguin sanctuary. Our nearest shops and restuarants are in Simons Town about 4 klm away. Own transport is reccommended.

Chic Studio in Cairnside Simonstown with Sea Views
Modern, spacious, self catering apartment on mountain side overlooking False Bay, Glencairn beach and tidal pool. Facing East and enjoying spectacular sunrises over sea and mountain this two person apartment is situated near top rated restaurants, shopping malls, scenic drives and world renown tourists attractions within easy reach. Away from busy city life, this luxurious unit based in Cairnside, Simon's Town is close enough to enjoy peace and tranquility in a modern and secure environment.

Unbelievable Sea Views from balcony in Simonstown!
Views, Views, Views is what this beautiful, comfortable apartment offers. Uninterrupted sunrise views are out of this world! Up on a hill, fully equipped, light & bright. 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 & much more. (Not suitable for loud parties, we are in a complex & must consider our neighbors)

"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.

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.

(2) Sun Sea Sleep - Simon's Town Cape Town - 1 bed
ONLY TWO PEOPLE ALLOWED. Private self-catering apartment, one bedroom, one bathroom, lounge, study, kitchen, dining area and exclusive balcony. Equipped with Fridge, induction stove, pots pans, microwave. Shampoo, lotion, coffee, tea/sugar. There is a walk way to another apartment past this apartment. We are situated in picturesque Simon's Town, 45 kilos from Cape Town international airport, 4 kilos drive from the famous Boulders beach and 21 kilos from Cape Point National park.

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.

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.

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.

Glen Eden loft style studio with sea/mountain view
Glen Eden Studio: this modern, light and airy loft style studio apartment is nestled in the trees and boasts beautiful sea and mountain views. It is set in a residential neighbourhood within walking distance to the beach, hiking trails and wetland reserve. A perfect base to experience the outdoor activities in the area, explore the quirky towns and restaurants nearby or to just chill out and enjoy the views and tranquility.

Simons Town self catering apartment
Fully equipped seaside apartment with separate Kitchen and Bathroom. Double bed, sleeps two. Free WiFi. There is a Washing machine installed in the kitchen. There is a hair dryer so no need to bring one along. Short walk to beautiful beaches and Penguin viewing. Ten minute walk to the center of town, Naval Museum & restaurants. Parking for one vehicle. It is a friendly safe neighborhood.
Popular amenities for Simon's Town holiday rentals
Other great holiday rentals in Simon's Town

Jamiesons hide away

Shamayim Katan (Little Heaven)

Gleneagle Cottage - Quiet. Comfortable. Practical.

Luxury Ocean-front 1BR Apartment at Harbour Bay

The Pearl, Views over Long Beach. Backup power.

Spekboom Studio - Glencairn near Simonstown

3 Bedroom Cottage in the heart of Simon’s Town

The Carved Rock-Entire studio
Quick stats about holiday rentals in Simon's Town
Total rentals
430 properties
Nightly prices starting at
$26 SGD before taxes and fees
Total number of reviews
15K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
80 properties have a pool
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- Glencairn Beach
- Fish Hoek Beach
- Muizenberg Beach
- Long Beach
- Big Bay Beach
- Boulders Beach
- Clifton 4th
- GrandWest Casino and Entertainment World
- Hout Bay Beach
- Woodbridge Island Beach
- Green Point Park
- Sandy Bay, Cape Town
- St James Beach
- Babylonstoren
- District Six Museum
- Greenmarket Square
- Mojo Market
- Two Oceans Aquarium
- Durbanville Golf Club
- Waterkloof Wine Tasting Lounge
- Noordhoek Beach
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Steenberg Tasting Room