Vacation rentals in Simon's Town

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Top-rated vacation rentals in Simon's Town

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Top guest favorite
A balcony provides an unobstructed view of the sea and coastline, with clear blue waters stretching into the horizon. The surrounding greenery frames the scenery, while the homes below are visible, showcasing a mix of roofs and vegetation.
Guest suite in Simon's Town
4.99 out of 5 average rating, 305 reviews

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.

Top guest favorite
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, 250 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 favorite
Villa in Simon's Town
4.9 out of 5 average rating, 241 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 favorite
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
4.98 out of 5 average rating, 128 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 favorite
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, 116 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 favorite
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, 115 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 favorite
A serene sunset is showcased over the calm ocean, with warm orange and yellow hues blending into the horizon. Lush foliage and vibrant flowers are visible in the foreground, and a simple home can be seen in the background, nestled among the greenery.
Cottage in Simon's Town
4.91 out of 5 average rating, 164 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 favorite
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, 304 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.

Guest favorite
A welcoming living area features a soft-colored sofa and light chairs, arranged around a low table. Natural light filters through sheer curtains, highlighting a decorative painting on the wall. A vase of fresh flowers adds a touch of warmth, creating a comfortable space for relaxation.
Home in Simon's Town
4.84 out of 5 average rating, 142 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 favorite
A private patio offers sweeping views of the ocean and surrounding landscape. Light-colored outdoor furniture provides a comfortable space for relaxation. The horizon showcases a clear blue sky, extending above the tranquil water, while the distant coastal town is visible beneath the hills.
Apartment in Simon's Town
4.97 out of 5 average rating, 469 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 favorite
A cozy sleeping area features a comfortable double bed with soft linens and two bedside lamps for soft illumination. Artwork adorns the walls, and a small desk is positioned nearby. A window allows natural light to fill the space, with garden views visible outside.
Apartment in Simon's Town
4.88 out of 5 average rating, 325 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 favorite
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
4.9 out of 5 average rating, 292 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.

Popular amenities for Simon's Town vacation rentals

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

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Avg. priceG$19,412 GYDG$17,116 GYDG$17,324 GYDG$17,324 GYDG$16,281 GYDG$14,611 GYDG$15,028 GYDG$15,863 GYDG$15,654 GYDG$15,863 GYDG$16,281 GYDG$19,412 GYD
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Quick stats about vacation rentals in Simon's Town

  • Total vacation rentals

    Explore 430 vacation rentals in Simon's Town

  • Nightly prices starting at

    Simon's Town vacation rentals start at G$4,175 GYD per night before taxes and fees

  • Verified guest reviews

    Over 14,590 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wi-Fi availability

    420 of Simon's Town vacation rentals include wi-fi 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!

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