Vacation rentals in Simon's Town

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Quick stats about vacation rentals in Simon's Town

  • Total vacation rentals

    Explore 440 vacation rentals in Simon's Town

  • Nightly prices starting at

    Simon's Town vacation rentals start at G$4,183 GYD per night before taxes and fees

  • Verified guest reviews

    Over 15,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    220 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!

Top-rated vacation rentals in Simon's Town

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

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Top guest favorite
A modern apartment interior is visible with large windows offering a view of the ocean. A spacious bed is adorned with colorful pillows. A small dining area contains a table and chairs, and a cozy seating arrangement features two wicker chairs near the window.
Apartment in Glencairn
5.0 out of 5 average rating, 129 reviews

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.

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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
4.92 out of 5 average rating, 293 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)

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Guest favorite
An open living area features sliding glass doors that lead to a patio with a scenic view of the ocean. A playful sun sail provides shade, while a lounge chair and a unique outdoor game surface enhance the relaxing atmosphere.
Apartment in Glencairn
4.91 out of 5 average rating, 116 reviews

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

LocationFamilyLong stay

Top guest favorite
Villa in Simon's Town
4.95 out of 5 average rating, 106 reviews

180°SeaViews•Big Villa• Beaches•Penguins

Price include Airbnb 15.5% fee. Wake up to sweeping ocean views. Villa perched on hillside in Simon’s Town. Easy, well marked, walks to many penguin colonies, & secret wind free beaches. Chef’s kitchen fully equipped. A big balcony with big BBQ. Indoor built-in BBQ fireplace for heating areas/cooking. Gas heaters in all bedrooms. Back up Inverter & solar geyser if electricity disruption. Stable fiber& mesh system. Smart TV in bedrooms. High quality beds & linen Lots activities to suit all ages

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Guest favorite
A spacious living area features large windows offering views of the ocean. A round wooden table sits center, complemented by a decorative bowl. A chandelier hangs above, while blue and white patterned armchairs provide seating. The room is enhanced by soft lighting from the curtains.
Apartment in Fish Hoek
4.92 out of 5 average rating, 195 reviews

Apartment with panoramic ocean and mountain views

A minute walk from the beach, this space is ideal for you to recharge and reset. Grab a bit to eat in the picturesque fishing village of Kalk Bay before taking a sunset stroll along the catwalk. With no shortage of activities from a round of golf at the Clovelly Golf Course, spying on the penguins residing at Boulder’s Beach as they go about their business to catching a wave at Muizenberg surfer’s corner. You are perfectly located to take advantage of all the Southern Penisula has to offer.

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Top guest favorite
Villa in Simon's Town
4.92 out of 5 average rating, 288 reviews

Cape Point Mountain Getaway - Oceanside 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.

LocationFamilyGetting around

Top guest favorite
A charming cottage with a dual-level design is framed by vibrant pink flowering plants and lush greenery. The white exterior is complemented by wooden shutters, and the balcony features white railings that overlook the entrance. The mountain backdrop adds to the serene setting.
Cottage in Simon's Town
4.95 out of 5 average rating, 102 reviews

3 Bedroom Cottage in the heart of Simon’s Town

A beautiful cottage situated in the heart of historic Simon's Town. Perfect for exploring the Southern Peninsula. Watch the sunrise over False Bay from the balcony. A short walk down the historical Drostdy Steps to Jubilee Square, you will find great restaurants with idyllic views of the yacht basin. Stand-up paddle boarding, kayaking and ferries are available right there. The famous Boulders Beach with its colony of penguins is nearby, as are the beaches. Cape Point is a short drive away.

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Guest favorite
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
4.92 out of 5 average rating, 119 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.

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Top guest favorite
A dining table with several chairs is positioned on a deck, overlooking a calm bay. In the distance, mountains are visible along the shoreline, while a singular ship floats on the water. The scene is bathed in soft light, suggesting dawn or dusk.
Home in Cape Town
4.95 out of 5 average rating, 195 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.

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Superhost
An elevated view from the sun deck showcases sweeping ocean vistas, framed by gentle mountain contours. The wooden deck is complemented by greenery, enhancing the serene atmosphere. The clear sky allows for ample natural light, creating an inviting outdoor space for relaxation.
Home in Simon's Town
4.81 out of 5 average rating, 273 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. Twenty minutes walking distance to the village shops and restaurants. Seven to ten minutes walk to the choice of beaches and penguins. The house can accommodate 6 guests in 3 bedrooms, each with an ensuite bathroom. If you are looking for a beautiful place to relax, refresh and renew, then this is the home for you!

ValueFamilyLaundry

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
4.83 out of 5 average rating, 174 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.

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Top guest favorite
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, 210 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

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Popular amenities for Simon's Town vacation rentals

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

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,098 GYDG$23,215 GYDG$20,287 GYDG$19,451 GYDG$16,732 GYDG$16,313 GYDG$15,059 GYDG$15,895 GYDG$15,686 GYDG$17,987 GYDG$18,196 GYDG$24,261 GYD
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