Holiday rentals with a pool in Simon's Town

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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.

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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 Noordhoek
4.88 out of 5 average rating, 219 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 Cape Town
4.84 out of 5 average rating, 147 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

Guest favourite
Home
4.94 out of 5 average rating, 232 reviews

Dream Family Villa CapeTown-StunningSeaView

If you dream of an unforgettable FAMILY Stay in a fantastic villa in Western Cape, in a very quiet neighborhood: indulge yourself at SummerPlace, fully equipped w/ SOLAR PANELS/INVERTERS/BATTERIES. Our stunning contemporary home is backed by a super bright mountain w/ panoramic views of False Bay. Breath taking views of the ocean are in absolutely every window, in every bedroom, living room areas, kitchen... Enjoy both pool and beach (7min walk), take a deep breath: this beauty is all yours.

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, 164 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 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 Cape Town
4.92 out of 5 average rating, 118 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
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 Cape Town
4.97 out of 5 average rating, 118 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 Cape Town
4.97 out of 5 average rating, 119 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 Cape Town
4.91 out of 5 average rating, 193 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.

Superhost
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 Cape Town
4.87 out of 5 average rating, 141 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 Cape Town
4.84 out of 5 average rating, 208 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

Guest favourite
Villa in Cape Town
4.93 out of 5 average rating, 151 reviews

28 Break-Away, Castle Rock Cape Town Luxury Villa

Located in the Castle Rock marine nature reserve just past Miller’s Point in False Bay. This beautiful seaside home boasts the best of luxury living, giving you a direct connection with the ocean. Peace and tranquility are in abundance as the ocean caresses every space in the house with her sounds , smells and sights. There is a local baboon troop in the area . Please be vigilant!

Superhost
An open living area features a modern design with large glass panels offering unobstructed ocean views. A spacious white lounge chair is positioned beside a wooden coffee table. Soft orange and blue cushions provide comfort on the sofa, enhancing the relaxed atmosphere.
Home in Scarborough
4.91 out of 5 average rating, 155 reviews

Exclusive Tree House Hideaway

Reminiscent of a Robinson Crusoe island hideaway, this private haven with endless ocean views is magically situated amongst gnarled trees and rocks in the tranquil coastal village of Scarborough. A luxurious sanctuary of impeccable taste and design.

Popular amenities for Simon's Town rentals with a pool

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Avg. price£100£104£89£86£106£61£76£72£89£90£94£137
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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 3,830 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • 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

  • 4.8 Average rating

    Simon's Town stays are highly rated by guests – averaging 4.8 out of 5!