
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 $44 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

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

4.8 Average rating
Simon's Town stays are highly rated by guests—averaging 4.8 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.

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.

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.

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.

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!

Solar Powered Cape Town Villa with fantastic views
unfortunately we cannot host kids between 2 and 12 Beautifull villa with four bedrooms and four bathrooms plus swimming pool and garage. Situated on Fish Hoek Mountain with fantastic views of Fish Hoek Valley and False Bay. The villa is equipped with solar panels and backup for power.

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
House rentals with a pool

The Lookout

Villa Ondine: Cape Town Beach House

Honeymoon Lighthouse Cottage - sea view, pool, BBQ

Dream Family Villa CapeTown-StunningSeaView

Blackwood Log Cabin

Sapphire Sunset. Panoramic Views. Solar backup

Peaceful Green Oasis with Sea View

Ocean Song | Seafront Escape with Epic Views!
Condo rentals with a pool

On the Rocks in Bantry Bay

Breathtaking Ocean views, Nature surrounds

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

Mountain View Penthouse | Secure 2BR, Views & Pool

Amazing Ocean & Mountain Views From Trendy Condo

Modern Ocean View Retreat in Camps Bay

Tranquil, modern and well located next to mountain

Modern luxurious sea view apartment
Home rentals with a private pool

Watch the Sunrise in a Home with a Mountain View

Chic Penthouse with Private Pool & Breathtaking Views

Glen Beach Penthouse A on Glen Beach in Camps Bay

Constantia Klein 4 Bedroom Villa on the Vineyards
Contemporary Farmhouse with Garden and Pool
Terrace Suite - own pool, jacuzzi bath, fireplace

Chic Boutique-Hotel Feel at a Seafront Pad, Clifton
Solar-Powered Mountain Retreat with Natural Pool
When is the best time to visit Simon's Town?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $269 AUD | $224 AUD | $226 AUD | $168 AUD | $209 AUD | $120 AUD | $149 AUD | $142 AUD | $174 AUD | $177 AUD | $184 AUD | $269 AUD |
| 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
- Waterfront rentals Simon's Town
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- Rentals with pools Cape Town
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- Rentals with pools South Africa
- Fish Hoek Beach
- GrandWest Casino and Entertainment World
- V & A Waterfront
- Boulders Beach
- Cape Town International Convention Centre
- Green Point Park
- Glencairn Beach
- Bloubergstrand Beach
- Cape Town Stadium
- Cbd
- Muizenberg Beach
- Clifton 4th
- Hout Bay Beach
- Stellenbosch University
- St James Beach
- Babylonstoren
- Canal Walk Shopping Centre
- Atlantic Seaboard Community
- Noordhoek Beach
- District Six Museum
- Jonkershoek Nature Reserve
- Long Beach
- Glen Beach
- Cavalli Estate





