Holiday rentals with a pool in Simon's Town

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Top-rated rentals with a pool in Simon's Town

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A sunlit outdoor living area features comfortable seating amidst lush greenery. An infinity pool extends towards distant ocean views, enhancing the tranquil setting. Smooth wooden decking complements the natural stone structure, providing a seamless transition between indoor and outdoor spaces.
Condo in Noordhoek
4.88 out of 5 average rating, 209 reviews

Terrace Suite - own pool, jacuzzi bath, fireplace

On your deck is tumbling waters of the private infinity pool looking towards the distant horizon of the Atlantic, the Terrace Honeymoon Suite is perfect for that special occasion celebration. Jacuzzi bath, gas fire plus fabulous indoor/outdoor living. DSTV with SuperSport, Wifi, BBQ. African Violet is 10 minutes drive to beaches of your choice, and close to Boulder's penguins, Cape Point, Table Mountain, V&A Waterfront, wine routes, shops, banks, top restaurants, quaint working-harbours etc There is a private entrance to this apartment. The setting is really special, as the view over the infinity pool, of the ocean is framed by greenery. There is indoor/outdoor living for summer and a fire-place for the chill of winter nights. Off street parking is provided We are here is assist with any queries, plans for the day, restaurant reservations etc. The home is located in a quiet neighbourhood close to beaches, Boulder's penguins, Cape Point, Table Mountain, V&A Waterfront, shopping, wine routes, award-winning restaurants, and quaint harbours. Most guests hire a car - but recently more and more are using Uber taxi We are registered with the local paramedics organization who can assist swiftly in any medical emergency.

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
Villa in Simon's Town
4.91 out of 5 average rating, 254 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.

Top Guest favourite
A spacious outdoor deck features a wooden seating area with plush cushions, overlooking the ocean waves. A small round table holds potted plants, and the backdrop consists of rugged cliffs under a clear blue sky, creating a serene coastal environment.
Home in Misty Cliffs
4.99 out of 5 average rating, 154 reviews

Seaside Mountain Retreat in Misty Cliffs w/ Sauna

Seaside mountain retreat in exclusive Misty Cliffs nature reserve with endless views, pool and large fynbos garden with private path down to the beach. This architect designed wooden bungalow is perfect for exploring Cape Point and the Southern Peninsula or just switching off and relaxing in the verdant immersion of a conservation village. Featuring 2 large en-suite bedrooms as well as a cosy loft and additional bunkbeds for the kids. The house is just 45 minutes from Cape Town city centre.

Top Guest favourite
A modern wood and glass home is positioned directly on the beach, with expansive outdoor decking. Loungers are arranged on one side, while a dining area is visible toward the indoor space. Lush greenery lines the perimeter, contrasting with the sandy surroundings.
Villa in Kommetjie
4.99 out of 5 average rating, 175 reviews

Amazing home on the beach in Klein Slangkop

Modern wood and glass home with solar-heated pool on the beach in Klein Slangkop private security estate. Step from the front deck onto beautiful beach sand and direct access to some of the most pristine beaches in the Cape. Breathtaking views. Great surfing. Nature. Stunning sunsets. Situated on the west coast of the Peninsular 50 minutes to Cape Town City Center one way and 25 mins to Cape Point gate the other way. Noordhoek beach is to the right and Long Beach to the left of the house.

Top Guest favourite
A spacious studio room features a queen bed, accented by bedside wall lights. A dining area for two is positioned nearby, along with a comfortable armchair. A vibrant artwork adorns the wall, enhancing the neutral tones of the decor, while natural light fills the space.
Guest suite in Simon's Town
4.94 out of 5 average rating, 109 reviews

Spacious poolside Studio

Glencairn, tucked away between Fish Hoek and Simons Town you will find Sea Holly. With decor inspired by the blue mussel shell makes for a tranquil setting. A super practical linear kitchen with a cute dinning area. A Queen bed flanked by wall lights opening up the space on the bedside tables. The arm chairs are great for relaxing after a fun filled day. Attractions: Glencairn beach and Tidal pool only 7min walk, amazing local restaurants and shops with fresh produce and chemist 5min walk.

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
A clear view of the private pool is framed by large glass windows, showcasing its inviting turquoise water. Surrounding greenery and the ocean can be seen in the background, creating a serene atmosphere, with sunlight reflecting off the water's surface.
Apartment in Simon's Town
4.92 out of 5 average rating, 138 reviews

Whale Rock Apartment. A true Cape Town holiday.

WHALE ROCK Apartment is named after the imposing granite boulder standing in the ocean below, where "My Octopus Teacher" was filmed. A stunning patio provides your entrance, and your pool deck leads off the patio. Views across False Bay can be enjoyed from every angle. While being able to enjoy the beautiful accommodation, guests will also be within walking distance of world famous beaches, as well as being a short drive away from Cape Point, and from the quaint centre of Simons Town.

Top 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.
Apartment in Simon's Town
4.97 out of 5 average rating, 112 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.

Top Guest favourite
A view of False Bay is captured, featuring gently rippling water reflecting soft orange and pink hues from the sky. Small boats are visible in the water, and the surrounding landscape includes buildings and foliage, offering a serene coastal atmosphere.
Cottage in Simon's Town
4.97 out of 5 average rating, 118 reviews

"Westmore" Self-catering Holiday Flat

Visit historic Simon's Town, a very special community in the southern end of Cape Town which boasts a thriving colony of African Penguins. We offer a beautiful self-contained apartment. It is within walking distance of the beach and the town center, including False Bay Yacht Club, for access to restaurants and quirky shops. You will have sweeping views over False Bay in your own private space. The outdoor entertainment area has a large pool and fireplace to enjoy the Cape evenings.

Guest favourite
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, 176 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.

Top Guest favourite
Apartment in Camps Bay
4.98 out of 5 average rating, 283 reviews

Primaview, Camps Bay, Cape Town

Primaview is situated in beautiful Camps Bay, Cape Town. Offering comfortable accommodation, alongside an inviting pool and surrounded by panoramic views of mountains and sea. Camps Bay is a scenic residential area, close to the city, as well as the famous Clifton Beaches. There are shops and popular restaurants along the Camps Bay Promenade. The Table Mountain Cable Way is a few minutes drive away. Access to nearby hiking trails are within a few minutes walk.

Popular amenities for Simon's Town rentals with a pool

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Avg. price$227 NZD$236 NZD$204 NZD$195 NZD$242 NZD$140 NZD$173 NZD$165 NZD$202 NZD$160 NZD$167 NZD$225 NZD
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Quick stats about holiday rentals with a pool in Simon's Town

  • Total holiday rentals

    Explore 100 holiday rentals in Simon's Town

  • Nightly prices starting at

    Simon's Town holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,940 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 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!