Vacation rentals with a pool in Simon&#x27;s Town

4.94 out of 5 average rating, 234 reviews

Home in Fish Hoek

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.

LocationValueParking

4.99 out of 5 average rating, 173 reviews

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

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.

FamilyLocationQuiet

4.94 out of 5 average rating, 118 reviews

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 Cape Town

Spacious poolside Studio @ Penguins & Pillows

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.

ValueFamilyLong stay

Guest suite in Simon's Town

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.

WHALE ROCK - Pavilion Suite - A true Cape holiday!

WHALE ROCK is the imposing granite boulder standing in the ocean below, where "My Octopus Teacher" was filmed. A stunning patio provides your entrance to the PAVILION SUITE, 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.

ValueLocationGrill

4.91 out of 5 average rating, 151 reviews

4.92 out of 5 average rating, 119 reviews

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

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.

FamilyValueAir conditioning

Vacation home in Fish Hoek

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.

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.

FamilyLocationNearby

5.0 out of 5 average rating, 105 reviews

Apartment in Simon's Town

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.

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.

ValueFamilyWifi

4.97 out of 5 average rating, 121 reviews

4.97 out of 5 average rating, 123 reviews

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

"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.

LocationValueDecor

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

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

ValueLocationOutdoor spaces

4.85 out of 5 average rating, 133 reviews

Apartment in Simon's Town

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.

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.

ValueLocationPool

4.87 out of 5 average rating, 151 reviews

4.84 out of 5 average rating, 210 reviews

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

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

LocationValueAccuracy

4.96 out of 5 average rating, 109 reviews

Cabin in Cape Town

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.

LocationValueIndoor spaces

Popular amenities for Simon's Town rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private veranda features a striped tablecloth on a dining table, accompanied by a vase of flowers. Double doors open to reveal scenic views of nature and the ocean beyond. Sunlight filters through the overhead slats, creating a dappled effect on the floor.

4.9 out of 5 average rating, 137 reviews

Honeymoon Lighthouse Cottage - sea view, pool, BBQ

FamilyValueWalkability

4.88 out of 5 average rating, 104 reviews

A large family kitchen features dark cabinetry, a central island with a gas stove, and ample counter space. Natural light floods the area through multiple sash windows, illuminating the wooden floor and brightening the inviting open-plan layout.

Home in Kalk Bay

Zonnendal Family Home in charming Kalk Bay

FamilyValueAccuracy

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.

4.91 out of 5 average rating, 156 reviews

Exclusive Tree House Hideaway

FamilyValueSleep quality

4.93 out of 5 average rating, 129 reviews

An open-plan dining area features a large wooden table surrounded by metal chairs, with panoramic views of the ocean through floor-to-ceiling windows. A kitchen counter with a stove and minimal décor complements the spacious layout, creating a relaxing ambiance with natural light.

Home in Saint James

The Lookout

LocationFamilyOutdoor spaces

4.8 out of 5 average rating, 367 reviews

Villa Ondine: Cape Town Beach House

FamilyLocationNearby

4.86 out of 5 average rating, 424 reviews

A wooden cabin is nestled among lush greenery and tall trees, showcasing a welcoming exterior with a covered deck. Large windows reflect the surrounding natural landscape, with the sun casting a warm light on the structure. The adjacent mountains provide a scenic backdrop.

Home in Hout Bay

Blackwood Log Cabin

LocationValueIndoor spaces

The exterior of a spacious beachfront home is shown, featuring a thatched roof and large open windows. A swimming pool and outdoor dining area are visible, surrounded by lush green landscaping. The backdrop includes nearby mountains and a clear blue sky, enhancing the tranquil setting.

4.89 out of 5 average rating, 141 reviews

Beachaven Kommetjie

LocationFamilyAccess

4.98 out of 5 average rating, 103 reviews

An inviting outdoor area showcases a swimming pool surrounded by wooden decking. Two lounge chairs are positioned beside the pool, offering a relaxing vantage point. The backdrop features majestic mountains and a clear blue sky, creating a serene setting.

Home in Hout Bay

Sunny 3 Bedroom House with Mountain Views

LocationValueQuiet

Condo rentals with a pool

4.88 out of 5 average rating, 101 reviews

A private patio features a hanging chair, offering panoramic views of False Bay and the surrounding mountains. Natural light casts intricate shadows on the stone flooring, enhancing the serene outdoor space, perfect for relaxation.

Condo in Fish Hoek

Breathtaking Ocean views, Nature surrounds

LocationPoolView

4.93 out of 5 average rating, 166 reviews

The open-plan living area features a spacious turquoise sofa, a round wooden coffee table, and a wall-mounted television. Natural light floods in through large windows, illuminating plants placed thoughtfully around the room. A cozy fireplace is positioned against a light grey wall, enhancing the inviting ambiance.

Condo in Kalk Bay

Kalk Bay - SeaViews. Patio. Pool. Fireplace. Braai

LocationFamilyLayout

4.94 out of 5 average rating, 162 reviews

Two sun loungers are positioned on a wooden deck, overlooking a scenic view of the coastline and mountains. Lush greenery frames the space, with potted plants adding a natural touch. A glass of wine and a bottle sit on a nearby table, enhancing the serene setting.

Condo in Hout Bay

Sea View, Luxury Apartment near by the sea

FamilyValueCleanliness

4.91 out of 5 average rating, 151 reviews

A cozy lounge area is showcased with two gray sofas positioned around a wooden coffee table. Large glass windows provide an unobstructed view of the ocean, with the sun setting on the horizon. A small potted plant is placed on the table, complementing the serene atmosphere.

Condo in Lagoon Beach

Spectacular Beachfront Apartment

ValueFamilyPool

4.92 out of 5 average rating, 182 reviews

A private plunge pool is set within a landscaped garden, surrounded by greenery. The water sparkles under sunlight, and the ocean can be seen in the background, enhancing the serene atmosphere of the space.

Condo in Camps Bay

Camps Bay The View Villa Gdn apt & Pvt Pool

LocationValueParks

Condo in Cape Town City Centre

A modern living area features large glass windows providing expansive views of the surrounding landscape. A comfortable sofa adorned with cushions faces a sleek coffee table, while a decorative plant adds a touch of greenery. A flat-screen TV is mounted on a light wood console.

Perfect Views Of Table Mountain and Atlantic Ocean

LocationValuePool

4.93 out of 5 average rating, 257 reviews

4.83 out of 5 average rating, 125 reviews

Condo in Clifton

Oceanfront Luxury Penthouse - Clifton Sunset Views

LocationFamilyBiking

4.96 out of 5 average rating, 187 reviews

Condo in Camps Bay

Sunset Ocean View Retreat in Camps Bay

LocationValueCondition

Home rentals with a private pool

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.

Condo in Capri

Terrace Suite - own pool, jacuzzi bath, fireplace

FamilyLocationKitchen

4.87 out of 5 average rating, 222 reviews

4.96 out of 5 average rating, 156 reviews

A large covered patio features comfortable seating with gray wicker chairs and a black-and-white tiled floor. The view extends to the lush garden, showcasing a private swimming pool and well-maintained greenery, with sun loungers positioned for relaxation.

Home in Constantia

Constantia Klein 4 Bedroom Villa on the Vineyards

FamilyValueCheck-in

4.91 out of 5 average rating, 394 reviews

An inviting pool area features smooth stone surfaces and a shaded umbrella. Two lounge chairs are positioned beside the pool, which reflects the surrounding mountains and greenery, offering a serene view of the Hout Bay Valley.

Guest suite in Hout Bay

Watch the Sunrise in a Home with a Mountain View

FamilyValueBreakfast

Luxe

An Eco pool is set amidst a lush landscape, featuring a wooden deck with a pergola overhead. The water reflects the blue sky and surrounding greenery, creating a serene environment. Natural stone accents are visible along the pool's edges, enhancing the tranquil setting.

Villa in Oranjezicht

Solar-Powered Mountain Retreat with Natural Pool

FamilyLocationGetting around

4.92 out of 5 average rating, 185 reviews

4.97 out of 5 average rating, 236 reviews

Two woven chairs are placed around a small table on a spacious outdoor terrace. Lush trees provide shade, and panoramic views of the surrounding mountains and valley are visible in the background. A bottle of champagne rests on the table, contributing to a relaxed atmosphere.

Home in Hout Bay

Owl Cottage -Fireplace, Pool, Sea & Mountain Views

FamilyValueQuiet

4.96 out of 5 average rating, 112 reviews

A sunlit terrace features a wooden lounge chair with light fabric cushioning, positioned beside a small table. A bottle of champagne and two fluted glasses are placed on the table, with the ocean and palm trees visible in the background.

Home in Camps Bay

Villa Claybrook - Camps Bay

ValueLocationCleanliness