
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 $50 NZD 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 and kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Simon's Town holiday rentals include Wi-Fi 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.

Sea Views Oceans Echo Luxury villa
Hi, I’m Yvette I’ve been hosting guests at my villa since 2007. Come SEE the SEA in all her Seasons with all your Senses! A piece of paradise in Cape Town’s Southern Peninsula, that has views spanning the entire False Bay coastline, from Simon’s Town to Muizenberg. I’m a born Cape Townian and am able to offer advice, give ideas for itineraries, and provide insider tips on restaurants and attractions in the Mother City. However your group is made up, I’d be happy to host and help You'all

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.

Watersmeet On the beach at 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.

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.

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.

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.

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.

"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.

Stunning Ocean View and Sound
Hear breaking waves. Luxurious villa with pool. Breathtaking views. Walk to best blue flag bathing beach in CT. Sheltered private solar heated pool. Bright architect designed home with floor to ceiling sliding doors. Garage. Comfortable hotel style. Inverter Electric Power(new), blackout curtains, cotton sheets, pocket sprung beds, aircon in reception rooms and two bedrooms; fast wi fi ; 75 inch Qled TV - option of wonderful housekeeper. Uber plentiful WINTER Warm aircon heat.

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

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

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
House rentals with a pool

Dream Family Villa CapeTown-StunningSeaView

Honeymoon Lighthouse Cottage - sea view, pool, BBQ

Zonnendal Family Home in charming Kalk Bay

The Lookout

Beachaven Kommetjie

Blackwood Log Cabin

Boho Ocean-View Villa: Pool & Walk to Beach

Moya Vista w/ Sauna, Hot Tub, Cold Plunge, Pool.
Condo rentals with a pool

Breathtaking Ocean views, Nature surrounds

Sea View, Luxury Apartment near by the sea

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

Modern Ocean View Retreat in Camps Bay

Perfect Views Of Table Mountain and Atlantic Ocean

Camps Bay The View Villa Gdn apt & Pvt Pool

Signature Home @ Waterfront Canals

Spectacular Beachfront Apartment
Home rentals with a private pool
Terrace Suite - own pool, jacuzzi bath, fireplace

Watch the Sunrise in a Home with a Mountain View

Hillside Penthouse with Spectacular Table Mountain Views

Owl Cottage -Fireplace, Pool, Sea & Mountain Views

Your Dream Home in Sunny Camps Bay

Constantia Klein 4 Bedroom Villa on the Vineyards

Chic Penthouse with Private Pool & Breathtaking Views
Solar-Powered Mountain Retreat with Natural Pool
When is the best time to visit Simon's Town?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $311 NZD | $259 NZD | $262 NZD | $222 NZD | $251 NZD | $193 NZD | $173 NZD | $165 NZD | $202 NZD | $205 NZD | $214 NZD | $311 NZD |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
Destinations to explore
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- Fish Hoek Beach
- GrandWest Casino and Entertainment World
- Cape Town International Convention Centre
- Boulders Beach
- Green Point Park
- Bloubergstrand Beach
- Cbd
- Glencairn Beach
- Cape Town Stadium
- Hout Bay Beach
- Stellenbosch University
- Muizenberg Beach
- Atlantic Seaboard Community
- Clifton 4th
- Canal Walk Shopping Centre
- St James Beach
- Noordhoek Beach
- Jonkershoek Nature Reserve
- Glen Beach
- District Six Museum
- Cavalli Estate
- Long Beach
- Newlands Forest
- Table Mountain





