Vacation 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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Guest favorite

Villa in Cape Town

4.94 out of 5 average rating, 178 reviews

Watch Penguins in the Garden of a Luxury Villa in Boulders

Dine al fresco on the covered deck and marvel at the incredible views over False Bay and an award-winning garden, in which 40 penguins live! This villa has been beautifully decorated by a top designer and all paintings are by the former resident artist. Enjoy the warmer clear water of the best secret beach below the house. House comes with full time staff. The most relaxing, safe and private holiday house. Ultra fast unlimited Wi-Fi and well kitted out with high quality everything - can stylishly host 16 for lunch. Cool in summer and warm in winter - it is the best place in the world! This is a very special holiday house indeed. It is blissfully quiet and private yet easily accessible. Great in winter too. One road back from the sea which is actually an advantage at Boulders Beach as it is hidden away from the many tourists. 100% 5-star reviews - a perfect Airbnb score. The view is unbelievable - bring your binoculars for whale and bird watching. The house has 2 bedrooms and 2 bathrooms and so does the cottage. The large award-winning garden was planted by Kirstenbosch botanical gardens' landscapers 30 years ago. Around 40 penguins live in the garden, which makes it one of the only houses in Africa that can boast that! Lottings the marvellous house manager / keeper is always on hand to help with anything and everything. There is also a games room with a table tennis table. Whale Song is an entertainer's paradise, fully equipped with everything you could hope for and high-end kitchen equipment etc. It is also a modest distance (40km) from Cape Tow, so invite friends to join you for a day or a night. Good old Bose surround sound Hifi with an aux cable so you can play your own music easily. Very quiet - no sign of a neighbour or a tourist. Close proximity to hotspots on the peninsular, including top restaurants and wine estates. Also suitable for corporate strategy getaways, teambuilding, photo / video shoots and experiential showcase meals and events. The house is super safe. has non intrusive CCTV and as it is next to a naval base with armed guards at entry to base over the rd from the house. There are two good new bicycles for you to borrow, as well as a blow up boat and some snorkelling and other beach gear. You won't ever want to leave - this is paradise on earth and is the most relaxing holiday house around. Entire place is yours. Access from the main rd and also a pedestrian gate with a code to Gay rd below. I'm always available to give advice or help with anything at all. Whale Song is a villa in Simon’s Town, a historic and increasingly trendy town. It has lovely restaurants, antique shops, and a great yacht club. Cape Point, endless hiking trails, SCUBA diving and swimming beaches are very close by. Rent kayaks and SUPs and enjoy the clear water and its rich marine life. Or just take it easy and relax before the wonderful view and many birds in the garden. The large patio is sheltered from the wind and is the best venue for hosting long sun drenched lunches! A car is handy but the house is serviced by main bus routes and is a 20 minute walk from the train station - it is then one hour by train (half of it along the coast) to the centre of Cape Town. The house is called Whale Song but it just as well might be named Penguin Song - we love the sound of the birds but be prepared to hear then chattering away till 10 at night and again from 7 in the morning in the garden!

Jun 13 – 20

€ 338 per night

Guest favorite

Condo in Sea Point

4.95 out of 5 average rating, 182 reviews

Breathtaking Ocean Views With Private Pool, Deck and Garden

Start the morning by stepping out onto a private balcony and taking in the beautiful sea views. Unwind in the open minimalist-inspired living area and soak in the sun on the spacious deck outside while firing up a BBQ next to the pool. The apartment is a freestanding bungalow that features its own separate entrance. All amenities including the pool and garden are private and exclusive use. The perfect place for a work-cation, with BACK UP POWER supply, stable, high-speed internet, work desk, coffee machine and beautiful scenery sure to boost productivity. Work, play or both. You've got it Private entrance - walk up from Ocean View Drive Gas BBQ with all amenities Pool loungers Sun deck Swimming towels provided 8 seater patio set - perfect for entertaining Private garden Washer/dryer Gas SMEG stove Nespresso coffee machine Cable TV High speed wifi Egyptian cotton sheets Private exclusive use garden and pool area/deck I’m available at most times and always happy to make sure my guests have the best experience The home is in a quiet neighborhood close to many of Cape Town's top attractions. Go for a walk through the picturesque Sea Point promenade to reach the stunning beaches and spend the afternoon hiking the iconic Signal Hill. Close to numerous great coffee shops, restaurants and cafes. With several large super markets, pharmacies, and the high street all within walking distance. Car, by foot, Uber/taxi or MiCiti bus (local bus system) 2 minutes walk to the local grocery store on Main Road - Woolworths 5 minutes walk to the Sea Point Promenade and Sea Point beaches 5 minutes walk to major shops, restaurants and bars 5 minutes walk to Mojo market Under 5km to the V&A Waterfront Under 5km to the CBD & Bree street Several local groceries stores within walking distance - Woolworths (Piazza St John's), Checkers and Spar are the closest. Dis-Chem - major drug store/pharmacy at the Checkers Centre Sea Point Medical Centre - 2 mins walk away, for GPs, dentists etc

Jun 19 – 26

€ 86 per night

Guest favorite

Guest suite in Cape Town

4.9 out of 5 average rating, 325 reviews

Watch the Sunrise in a Home with a Mountain View

The apartment is set high up on Little Lionshead with panoramic views of the Hout Bay Valley and the Helderberg mountains beyond. Folding doors lead onto an expansive pool deck with sun loungers and a gas barbecue all for the exclusive use of the apartment guests. There is a full kitchenette with oven, hob, microwave, fridge and freezer, an en suite bathroom, lounge area with a large flat panel TV and an open-plan dining area. The apartment is serviced daily except for Sundays and public holidays. We have solar and battery power so are not affected by power outages. Mountain Walks, Village atmosphere with a city 10 minutes away. Beach 2km away. The suite is located on the lower level of the property and is totally private. There is parking on the property. Pool, garden, Mountain We are available to transport you around the Cape, take you on wine tours at an additional fee. MacD, our housekeeper is on hand 24 hours to assist where necessary The house is safe and secure with guarded entrance. Wake up to birdsong and enjoy the surrounding majestic mountains. Mount Rhodes is a security estate nestled in the foot of Little Lions Head. Mycity bus stop at the bottom of the road, Uber We provide a laundry service at an additional cost and breakfast is available if ordered at least 24 hours before at an additional cost as well. I am also more than happy to make any reservations for tours or restaurants on your behalf.

Apr 4 – 11

€ 108 per night

Guest favorite

Villa in Simon's Town

4.87 out of 5 average rating, 167 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.

Nov 23 – 30

€ 88 per night

Guest favorite

Apartment in Kommetjie

4.94 out of 5 average rating, 319 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

Sep 30 – Oct 7

€ 108 per night

Guest favorite

Apartment in Cape Town

4.96 out of 5 average rating, 273 reviews

SeaView Townhouse. Beach, steps away. Spectacular!

A beautifully presented townhouse in a glorious beach location. Offering majestic sea, harbour & mountain views from all spaces. Top finishings & fittings throughout as well as a cosy fireplace. A sparkling pool completes the picture. Walking distance to a gym, restaurants & shops. Secure parking is provided within the private complex parking. The ultimate Cape Town holiday/ remote-working spot: Strong WIFI, Satellite TV, Netflix Loaded - loadshedding assisted with an electrical back-up unit.

Apr 6 – 13

€ 159 per night

Guest favorite

Home in Cape Town

4.99 out of 5 average rating, 108 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.

Jul 12 – 19

€ 387 per night

Guest favorite

Cabin in Kommetjie

4.99 out of 5 average rating, 148 reviews

Amazing home on the beach in Klein Slangkop Estate

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.

Mar 25 – Apr 1

€ 465 per night

Guest favorite

Apartment in Cape Town

4.99 out of 5 average rating, 111 reviews

5newkings: take a break, relax, explore!

This luxury apartment is the perfect place to unwind in. Nestled in a secure estate with 24hr security in the heart of Kalk Bay, it is a short walk from multiple popular destinations like Dangers Beach and Dalebrook tidal pool, surf spots, art galleries, and iconic restaurants. A short drive away are Simon's Town and St James, gems steeped in history. With beautiful furnishings and uninterrupted views, 5 New Kings is the place to enjoy yourself and explore this beloved Cape fishing village.

Aug 1 – 8

€ 163 per night

Guest favorite

Home in Cape Town

4.92 out of 5 average rating, 105 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.

Apr 17 – 24

€ 208 per night

Guest favorite

Guest suite in Camps Bay

5.0 out of 5 average rating, 160 reviews

Tranquil studio w/pool 100m from beach

Unwind on the poolside loungers after a busy day exploring and enjoy the view of Table Mountain. This spacious modern studio looks out onto your own exclusive use luxurious private pool patio. Go for a morning stroll along the beach, just 100 meters away. Use the study desk area indoors, or the large poolside table outside on the sheltered patio to work remotely with our high speed Fiber. The studio has backup lighting, air conditioning, Netflix and your own gated parking bay.

Aug 29 – Sep 5

€ 110 per night

Superhost

Villa in Simons Town

4.81 out of 5 average rating, 177 reviews

Surround Sea Views from a Hillside Villa, Solar Powered

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

Jul 3 – 10

€ 206 per night