
Holiday rentals with a pool in Simon's Town
Find and book unique homes with a pool on Airbnb
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.

Sea Views Oceans Echo Luxury villa
Hi, I’m Yvette I’ve been hosting guests at my villa since 2007. Ocean’s Echo is my home-away-from-home - 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’ve lived in Cape Town my entire life 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 happy to help.

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.

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.

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.

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

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!

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.

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

Zonnendal Family Home in charming Kalk Bay

Sunny 3 Bedroom House with Mountain Views

Sapphire Sunset. Panoramic Views. Solar backup

Tranquil Waterfront Hideaway with Stunning Views

Peaceful Green Oasis with Sea View

Bantry Bay Home with Atlantic Ocean Views

Mountain House

Beachaven Kommetjie
Apartment rentals with a pool

Stylish 1Bedroom - Large Balcony & Seaviews & 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

Stunning Studio Close To Beach

Modern Ocean View Retreat in Camps Bay

Parker’s Park Lagoon
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

Spacious Home - Mountain Views,Pool,Firepit & BBQ

Constantia Klein 4 Bedroom Villa on the Vineyards
Terrace Suite - own pool, jacuzzi bath, fireplace
Solar-Powered Mountain Retreat with Natural Pool

Table Mountain Home with Ocean View
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 | £138 | £114 | £116 | £86 | £107 | £62 | £77 | £73 | £89 | £91 | £94 | £138 |
| 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 |
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 £22 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!
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- Cbd
- Cape Town Stadium
- Fish Hoek Beach
- Bloubergstrand Beach
- V & A Waterfront
- GrandWest Casino and Entertainment World
- Muizenberg Beach
- Glencairn Beach
- Green Point Park
- Boulders Beach
- Long Beach
- Cape Town International Convention Centre
- Clifton 4th
- St James Beach
- Hout Bay Beach
- Stellenbosch University
- District Six Museum
- Babylonstoren
- Noordhoek Beach
- Tyger Waterfront Apartments Deck
- Jonkershoek Nature Reserve
- Big Bay Beach
- Cavalli Estate
- Newlands Forest





