Holiday rentals in Simon's Town

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Top-rated holiday rentals in Simon's Town

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Top guest favourite
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, 294 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 favourite
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.
Flat in Glencairn
5 out of 5 average rating, 114 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.

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.
Flat in Simon's Town
4.93 out of 5 average rating, 240 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)

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.
Flat in Simon's Town
4.98 out of 5 average rating, 123 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 rustic cottage is nestled among vibrant, blooming flora, featuring distinct red and yellow flowers. Sunlight casts a warm glow on the stone path leading up to the cottage, which is surrounded by lush greenery and towering mountain scenery in the background.
Cottage in Simon's Town
4.9 out of 5 average rating, 236 reviews

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.

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.
Flat in Simon's Town
4.99 out of 5 average rating, 103 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.

Guest favourite
An exclusive balcony offers breathtaking views of the ocean and mountains. Two white Adirondack chairs sit at the edge, overlooking a vibrant landscape with the coastline visible below. Planters with greenery line the balcony, enhancing the outdoor space.
Flat in Simon's Town
4.92 out of 5 average rating, 396 reviews

(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.

Guest favourite
The outdoor area features a private swimming pool framed by lush greenery and vibrant pink bougainvillea. The pool reflects clear blue skies, enhancing the serene ambiance. Sunlight filters through the leaves, creating dappled patterns on the patio, which invites relaxation.
Flat in Simon's Town
4.98 out of 5 average rating, 102 reviews

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.

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, 299 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 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.
Flat in Simon's Town
4.88 out of 5 average rating, 322 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.

Top guest favourite
The exterior of the studio apartment features a modern white facade surrounded by trees and lush greenery. A set of stone steps leads from the driveway to the entrance, while a garage door blends seamlessly with the overall design. A clear blue sky completes the scene.
Loft in Simon's Town
4.95 out of 5 average rating, 186 reviews

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.

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.
Flat in Simon's Town
4.97 out of 5 average rating, 109 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, free WiFi (40mps) and 50'' TV with Netflix Britbox YouTube and Spotify. The apartment is SOLAR POWERED so NO ELECTRICITY BLACKOUTS. Close to some excellent eateries, beaches and a tidal pool.

Popular amenities for Simon's Town holiday rentals

Quick stats about holiday rentals in Simon's Town

  • Total rentals

    430 properties

  • Nightly prices starting at

    € 17 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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