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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Top guest favourite
A serene private pool is framed by a wooden deck, with comfortable loungers positioned for sunbathing. The expansive view reveals mountains and the ocean, under a clear blue sky, creating a tranquil outdoor retreat.
Flat in Cape Town
4.95 out of 5 average rating, 398 reviews

Mountain and Sea view apartment 1

Hi we have a lovely fully equipped and completely private apartment with own entrance in the stunning sea side village of Kommetjie.Open plan kitchen/lounge leads to your own private pool,deck,BBQ area all overlooking the stunning white beaches / mountains .Free WIFI,Satelite TV. extra beds/cots for Kids. King size bed in main bedroom along with freestanding bath/shower both with the most gorgeous sea views. Enjoy the sunrise and glorious sunsets both from private deck and pool area . Thanks

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, 167 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.

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.

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.
Flat in Simon's Town
4.92 out of 5 average rating, 147 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
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, 101 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, 122 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 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
4.86 out of 5 average rating, 127 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

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, 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, 152 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!

Top guest favourite
A charming stone cottage is surrounded by lush greenery, featuring large windows that invite natural light. An outdoor patio area with a table and chairs offers a serene space for relaxation, while various plants and rocks enhance the natural setting.
Cottage in Hout Bay
5 out of 5 average rating, 214 reviews

Stone Pine Cottage, Hout Bay

The stone & wood cottage nestles in a wild garden, the bay, beach and village just a kilometer away. The previous owner, a bachelor in his day, used to entertain girl-friends here – and romance still rules in the one-roomed stone cottage, where the mezzanine bedroom has mountain and sea views.

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 Cape Town
4.91 out of 5 average rating, 156 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

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

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Avg. price$236 SGD$197 SGD$199 SGD$148 SGD$184 SGD$106 SGD$131 SGD$125 SGD$153 SGD$156 SGD$162 SGD$236 SGD
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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 $38 SGD 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!