Some info is shown in its original language. Translate

Holiday rentals with a pool in Simon's Town

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Simon's Town

  • Total holiday rentals

    Explore 90 holiday rentals in Simon's Town

  • Nightly prices starting at

    Simon's Town holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 3,780 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 of Simon's Town holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simon's Town rentals

  • 4.9 Average rating

    Simon's Town stays are highly rated by guests – averaging 4.9 out of 5!

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

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Superhost
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.
Apartment in Capri
4.87 out of 5 average rating, 222 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.

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, 170 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
The modern wood and glass home is set against a backdrop of cloudy blue skies. Large glass doors allow light into the living spaces, while the beachfront deck features outdoor seating and a dining area. Lush coastal vegetation surrounds the property.
Villa
4.99 out of 5 average rating, 182 reviews

Watersmeet On the beach Klein Slangkop Kommetjie

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.

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
4.92 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.

Top guest favourite
A private splash pool sits on a deck, offering unobstructed views of False Bay and the coastline. The surrounding railing provides safety while enjoying the striking scenery of mountains and sea under a clear blue sky.
Holiday home in Fish Hoek
5 out of 5 average rating, 105 reviews

Bay View - Self Catering Apartment

Bay View apartment offers quality accommodation high up on the Fish Hoek Mountain providing spectacular views of False Bay, the Atlantic Ocean in the west and surrounding mountains. Guests enjoy two spacious bedrooms, an open plan lounge, dining/working area, a fully equipped kitchen with quality appliances, private patio and communal pool all with spectacular views, a modern bathroom (shower no bath), WiFi and premium DSTV. Not ideal for small children as close supervision is required.

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
4.97 out of 5 average rating, 121 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, 123 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 coastal view is captured, showcasing a modern multi-level house nestled among green vegetation. The ocean stretches to the horizon, with rocky formations visible in the water. Mountains rise gently in the background, creating a picturesque natural setting.
Home in Simon's Town
4.94 out of 5 average rating, 135 reviews

Boulders Seaside Home by Steadfast Collection

Charming, homey and convenient, Coppers is just 100m to the entrance to Boulders Beach. With views from every bedroom – the sunrise is not to be missed, nor the night skies and moonlit water, – and 180-degree vistas from Simonstown, around False Bay to Hangklip, the southern ocean swells and fishing boats coming in from Cape Point, it’s the textbook definition of a coastal idyll. Top tip: walk across the golf course before the tourists arrive and swim at Windmill Beach.

Superhost
A sun-drenched outdoor terrace features a spacious sunbed under a large umbrella. Lush green plants provide a touch of nature, while the sweeping ocean view creates a tranquil setting. Seashell decor adorns the nearby railing, enhancing the coastal ambiance.
Home in Misty Cliffs
4.85 out of 5 average rating, 132 reviews

Shangri La in Misty Cliffs

Shanglira is set on 3 levels with 4 bedrooms and 4 bathrooms ! The fourth bedroom and bathroom being a separate flatlet ! Pool decks , sunsets , barbecues etc are what you want here! Fully equipped kitchen with coffee machines washing machine tumble dryer dishwasher ! Bathrooms all have shower gels etc for you also free unlimited purified water! Pl remember we have doggie beds as well xx NO pets live on the property! But yours are welcome

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.
Flat in Simon's Town
4.88 out of 5 average rating, 149 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.

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, 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

Top guest favourite
Cabin in Cape Town
4.97 out of 5 average rating, 106 reviews

Shamayim Katan (Little Heaven)

Welcome to our tranquil haven in the sky. Nestled at an elevated vantage point, our charming cabin presents sweeping ocean views for an exceptional Scarborough experience. Ideally located for both surfers and nature enthusiasts, this peaceful retreat is only moments away from pristine beaches and the remarkable Cape Point Nature Reserve. Drift off under a canopy of stars and awaken to the clouds at your window.

Popular amenities for Simon's Town rentals with a pool

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

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£136£113£115£97£110£85£76£72£88£90£93£136
Avg. temp22°C22°C21°C18°C15°C13°C13°C13°C15°C17°C19°C21°C