Holiday houses in Simon's Town

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Top-rated holiday rentals in Simon's Town

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

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Guest favourite
A private deck is surrounded by lush greenery, featuring two modern stone chairs and a circular low table. The outdoor area leads to a swimming pool and a cozy nook with wooden accents, offering a relaxing space for outdoor enjoyment.
Guest suite in Simon's Town
4.85 out of 5 average rating, 143 reviews

Compass Cottage, Betwixt Sea and Mountains

Unwind in this creative quiet, chilled space, close to Boulders Beach, set in the Historical Mile, central Simonstown. Eclectic design, and calming colors are on display throughout the intimate guest suite. A Fully contained space, all you need for a short or long stay. The private deck and garden are a true standout with a quiet reading nook. A minute drive to the secret beach and a two minutes walk to town, central and safe! Please note; this space is for 3 Adults Or 2 Adults and 2 children. Own entrance with security. Your own deck and private garden with deck chairs. As much as they need! I live upstairs... Simonstown is filled with history and old buildings. Loads of cafes, restaurants, cute pubs, boutiques and near the yacht basin and waterfront area, all in walking distance. It's safe, peaceful, and close to the beach. Either hire a car, or Uber, or jump on the Metrorail. Train station 5 minutes away... Will whisk you to all the trendy spots in Kalk Bay and Muizenberg. Hire Bicycles and tour the peninsula The entire cottage and patio garden are non smoking, please respect our rules

Top Guest favourite
An enclosed balcony features a round table set for two, surrounded by white chairs. A stunning view of the ocean and distant mountains is visible through the glass sliding door, with soft hues of orange and pink from the sunset casting a warm glow.
Apartment in Simon's Town
4.93 out of 5 average rating, 257 reviews

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)

Top Guest favourite
A bright and spacious sleeping area features a queen-sized bed with soft bedding and decorative pillows. Large glass doors open to a deck with ocean views. Colorful artwork adorns the walls, complemented by natural light and neutral furnishings.
Apartment in Simon's Town
4.99 out of 5 average rating, 136 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
A bright living area is visible, featuring a dark ottoman and large French doors that open to a patio with ocean views. A white chair is positioned nearby, and greenery can be seen through the open doors, enhancing the spacious feel of the room.
Apartment in Simon's Town
4.99 out of 5 average rating, 122 reviews

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.

Top Guest favourite
A well-lit studio space features large glass sliding doors that open to a balcony overlooking the shimmering waters of False Bay. A cozy lounge area with a TV and a comfortable sofa is visible, complemented by soft curtains that frame the view.
Apartment in Simon's Town
4.97 out of 5 average rating, 124 reviews

Cairnside Studio Apartment

This new studio apartment is situated in the quiet exclusive suburb of Cairnside Simon's Town and enjoys stunning views over False Bay. The apartment has a fully equipped kitchenette with a 2-plate stove with mini oven, along with a combination microwave and Nespresso coffee machine (pods included). Free WiFi (40mps) and 50'' TV with Netflix, Spotify and a sound system. The apartment is SOLAR POWERED so NO ELECTRICITY BLACKOUTS. Close to some excellent eateries, beaches and a tidal pool.

Guest favourite
The exterior of a modern home features a pool surrounded by a wooden deck, with a view of the ocean in the background. Large windows reflect sunlight, and various potted plants add a touch of greenery. Clear skies and sailboats can be seen on the tranquil water.
Home in Simon's Town
4.91 out of 5 average rating, 115 reviews

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.

Guest favourite
Large windows with modern frames provide stunning views of the water and mountains. A cozy seating area features a light-colored sofa adorned with soft cushions, while a small table is decorated with a plant and a vase of flowers, adding a touch of nature to the interior.
Loft in Simon's Town
4.86 out of 5 average rating, 308 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
A private patio area features a round table with four chairs, overlooking a tranquil pool. Lush greenery surrounds the space, while panoramic ocean views set a serene backdrop under a clear blue sky. A Weber barbecue is visible, adding to outdoor dining options.
Apartment in Simon's Town
4.92 out of 5 average rating, 128 reviews

Penguin Apartment. Pool. Stunning sea views

Spacious beautiful modern apartment with amazing wide sea view, and a private patio and pool. In short walking distance to mountain (5 min up the road through guinea fowl sanctuary), a minutes walk to the shore, 1km from Fisherman's beach (with penguin viewing nearby), just 5 minutes from Simonstown centre, 15 minutes drive to Cape Point Nature reserve. Peaceful refuge for both business and holiday visits. Great location for divers too.

Superhost
A spacious studio apartment features large windows that open to stunning views of the Atlantic Ocean. A comfortable bed is complemented by a plush blanket. A cozy seating area includes a round table and black chairs, blending seamlessly with stylish decor and an elegant rug.
Apartment in Misty Cliffs
4.89 out of 5 average rating, 308 reviews

Dream View Studio

Dream View Studio is a dreamy 1 bedroom Misty Cliffs hideaway, located on a beautifully preserved mountainside, this studio apartment offers magical views of the Atlantic Ocean and the Baskloof Nature Reserve, perfect for those looking to relax in a private space surrounded by exquisite nature and enjoy the wide range of activities the area has to offer. A beautiful space for a sneaky weekend away or over night stays exploring the area.

Top Guest favourite
A tranquil outdoor space features a pool with clear water, surrounded by stone tiles. Two sun loungers are positioned near the edge, offering a view of the nearby mountain and bay. Natural light enhances the serene atmosphere, with greenery framing the area.
Villa in Simon's Town
4.84 out of 5 average rating, 205 reviews

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

Top Guest favourite
A white wooden deck features a round table and two chairs, surrounded by lush greenery. A cozy bench is adorned with a colorful blanket, while panoramic ocean views under a clear blue sky create a serene atmosphere.
Cottage in Boulders
4.96 out of 5 average rating, 232 reviews

Breathe the Ocean Air at a Charming Beach Cottage

Send a text / whats app and I will respond as soon as I can Wind-protected Boulders Beach is world-famous and home to penguins. Take a relaxing walk along the scenic Willis Walk boardwalk and watch them in their natural habitat. Watch out for the southern right whales from June to November.

Top Guest favourite
A spacious bedroom features exposed brick walls and a large window offering sea views. A comfortable bed is dressed in a patterned duvet, with towels arranged neatly at the foot. A dark armchair and decorative light fixture complement the inviting space.
Apartment in Simon's Town
4.95 out of 5 average rating, 168 reviews

Simon’s Town apartment with stunning sea views

Our free-standing garden apartment is a spacious, recently renovated double-storey flat with stunning sea and harbour views from every window. You will be a 1 km (13 min) walk from the quaint and historic town center of Simon’s town, which has many lovely restaurants, shops and amenities.

Popular amenities for Simon's Town holiday rentals

When is the best time to visit Simon's Town?

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Avg. price$162 NZD$143 NZD$145 NZD$145 NZD$136 NZD$122 NZD$125 NZD$132 NZD$131 NZD$132 NZD$136 NZD$162 NZD
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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 $52 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    440 of Simon's Town holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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!

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