
Holiday rentals with a pool in Overstrand Local Municipality
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Overstrand Local Municipality
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Westcliff Balcony Room
Welcome to this serene and spacious upstairs apartment - with a pool on the one side and a balcony with amazing sea view on the other side. The room itself is warm, cosy and arty. There is plenty of storage, places to sit and relax, access to the pool and safe off street parking. What I love about the room is the feeling you get when you're there... it seems to say 'you're on holiday.. relaaaaxx'. Other 2 apts on the property: /h/westcliff-pool-room-hermanus /h/westcliff-garden-room-hermanus

Stunning 6 Bedroom Seaside Family Home with Pool
Have fun & relax at this stylish seaside home. Our 16 sleeper includes 4 upstairs bedrooms, all en suite with walk-in showers & double basins, plus 2 family rooms downstairs. All bedrooms offer King Sized beds with stunning views of the bay or mountains. The open plan kitchen leads to a dining room & outdoor pool deck with breathtaking views. The home is steps away from the cliff path which leads to beautiful Stanfords Cove beach. BACK UP POWER AT THE HOUSE FOR ‘ESSENTIALS’ WHEN LOAD SHEDDING

Cottage on Fir Hermanus
Superb non-smoking garden cottage at the back of the main house. It sleeps 4 guests in two very luxurious en-suite double bedrooms (Air conditioned) with spacious TV- lounge and small kitchenette. (Well equipped). Expect good quality linen and fluffy towels and unexpected little luxuries. A sparkling pool, free parking and Fibre Wi-Fi on the premises. Guests can enjoy the garden and pool at leisure. It is completely separate and private as only one other person resides in the main house.

Oceanfront Villa 4br/4ba pool wifi, solar power
Whale Huys is a Self-catering, direct oceanfront villa with panoramic views of Walker Bay and the Klein Rivier Mountains. Perfect for a relaxing holiday away, just 2 hours from Cape Town. With its stunning views and just the sounds of nature, Whale Huys seems far removed from the busy hustle and bustle of our daily lives. but is close to the wineries and renowned country restaurants the area is famous for. Outdoor and cultural activities abound. Just 5 min. from Gansbaai for shopping.

Gledsmuir Spacious Homestead
Magnificent 47 hectare property set on the banks of the Klein River. The Thatched Homestead dates circa 1890’s and boast an ancient Oak Forest. Private and secure. The home offers 7 generous en suite bedrooms, a” Voorkamer”, dining room, two lounges, spacious modern farm styled kitchen in American Walnut plus separate Garden Cottage. The North side of the home features large garden, a covered Veranda with bar overlooking a large 12 metre swimming pool with water features. Book now!

Luxurious comfortable 4 bedroom beach house
4 bedrooms, all on suite and state of the art amenities. Short walk to Onrus main beach and coastal paths. 5min drive from Hermanus and Hemel and Aarde wine route. Near 2 great golf estates. Open plan areas leading on to panel heated swimming pool. Outdoor entertainment area is decked with a fire pit set amongst beautiful views of the Overberg mountains. Safe and secure with full alarm system, backup electricity invertor system. Quiet and tranquil neighborhood, no parties/loud music.

Veranda House
A charming verandah equipped with dining and lounge furniture gives this house its name. The 3 bedroomed house contains a lounge, fully equipped kitchen, dining room and two full bathrooms, (one ensuite). One bedroom and bathroom is accessed from the covered Veranda and has easy access into the house through a door a few steps away. Out on the back stoep (porch) you’ll find your barbecue facilities under the Huilboerboon tree. The stoep area has an additional toilet and washbasin.

Ocean Rhythm Hermanus Premier sea-front apartment
It has a prime position in Hermanus at the waters edge, with uninterrupted panoramic view of Walker Bay through its floor to ceiling frameless windows. This allows fantastic whale watching opportunity in season. It is opposite a Spar store, and a 18 hole golf course. It has been newly designed and renovated by John Greenfield FRSA and had high end finishes and equipment. This is set within its own beautiful gardens, with leisure area. A new heated pool will be built in 2026

5 Bed Beach Bungalow w/ pool, fire-pit & solar
✨ Winter Weekender Special 👇🏼✨ This 5 bedroom, 5 en-suite bathroom beach bungalow provides the ideal setting for a relaxed vacation at the majestic Hermanus coast. While away the hours pool-side, or enjoy the mountain glow at sun-set around the fire-pit with loved ones. Just a short walk to the beach, The Bungalow is what holiday dreams are made of. Enjoy the fire-place & local wine-farms in the winter or enjoy the outdoor chill areas in the summer-time. Solar-powered ☀️

PROTEA Loft Cottage @ Grotto Beach
Protea Loft Cottage nestles under the branches of an old tree. Protea is the top unit of two cottages in a large garden. An airy open plan space, stylishly decorated with your comfort in mind. Open the sliding doors, sit back onto the comfy couch, and look out over the garden and swimming pool. My place is close to mountain contour paths, cliff paths, and beaches. You’ll love my place because it is peaceful, comfortable, has a beautiful sea view and is safe.

Flamingo Lake Cabin near Hermanus & Beaches
Escape to a Scandinavian-inspired log cabin perched on South Africa's Bot River Lagoon, where wild horses roam, flamingos glide, and the ocean is minutes away. This intimate nature retreat offers 2 bedrooms, 2 bathrooms, and a mezzanine, fully equipped with Wi‑Fi, Netflix, kayaks, and everything you need for a restorative getaway. Explore a 1000‑hectare estuary, stroll to empty beaches, or enjoy the estate's pool and tennis courts. Just 90 minutes from Cape Town.

*Central - Whale Watching Paradise -Self check in*
In the Central hub of Hermanus opposite the old harbor, close to all activities & amenities, the local market, restaurants & shops all in walking distance, this apartment's location is key! Free parking space, art galleries, whale museum and the whale coast walking path boast all views for whale watching, convenience is right at your doorstep. Wi-Fi, Netflix and many more offers this stunning spacious apartment offers!!
Popular amenities for Overstrand Local Municipality rentals with a pool
House rentals with a pool

Blues

Klein River Cottage, Stanford Getaway

Edenly House

Spacious Family home with pool.

Martin's Rest - A place to relax

Relax in comfort and style

Seabreeze Retreat

Forest View - Onrus Island - 5 Bedroom
Apartment rentals with a pool

Family Apartment 6

The Ship in Strand

Cliff Path Cottage

Hermanus Waterfront Apartment No.20

Stunning 3-Bed on the Strand Beachfront

Bright and airy Parisian Gem close to the beach

Thyme Out - Private Apartment

J Spot • Safe & Convenient • Backup Power
Home rentals with a private pool

The Salt Box Villa - Self catering - Strand
Villa in the Vineyard near Somerset West

Eclectic Family Home near Wineries

Harbour Studio
When is the best time to visit Overstrand Local Municipality?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $237 SGD | $206 SGD | $197 SGD | $159 SGD | $140 SGD | $142 SGD | $145 SGD | $151 SGD | $166 SGD | $174 SGD | $178 SGD | $245 SGD |
| 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 Overstrand Local Municipality

Total holiday rentals
Explore 950 holiday rentals in Overstrand Local Municipality

Nightly prices starting at
Overstrand Local Municipality holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 27,890 verified reviews to help you choose

Family-friendly holiday rentals
590 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
470 properties have a dedicated workspace

Wifi availability
930 of Overstrand Local Municipality holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Overstrand Local Municipality rentals

4.8 Average rating
Overstrand Local Municipality stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Overstrand Local Municipality’s top spots include Fernkloof Nature Reserve, Benguela Cove Lagoon Wine Estate and Betty's Bay Main Beach
Destinations to explore
- Cape Town Holiday rentals
- Langebaan Holiday rentals
- Plettenberg Bay Holiday rentals
- Hermanus Holiday rentals
- Stellenbosch Holiday rentals
- Knysna Holiday rentals
- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
- Mossel Bay Holiday rentals
- Betty's Bay Holiday rentals
- Breerivier Holiday rentals
- George Holiday rentals
- Fitness-friendly rentals Overstrand Local Municipality
- Rentals with a fireplace Overstrand Local Municipality
- Farm stay rentals Overstrand Local Municipality
- Rentals with a firepit Overstrand Local Municipality
- Smoking-friendly rentals Overstrand Local Municipality
- Rentals with a patio Overstrand Local Municipality
- Bed and breakfasts Overstrand Local Municipality
- Private suite rentals Overstrand Local Municipality
- Cottage rentals Overstrand Local Municipality
- Rentals with lake access Overstrand Local Municipality
- Rentals with breakfast Overstrand Local Municipality
- Rentals with beach access Overstrand Local Municipality
- Chalet rentals Overstrand Local Municipality
- Serviced apartment rentals Overstrand Local Municipality
- Hotel rooms Overstrand Local Municipality
- Rentals with outdoor seating Overstrand Local Municipality
- Holiday home rentals Overstrand Local Municipality
- Rentals with a kayak Overstrand Local Municipality
- Apartment rentals Overstrand Local Municipality
- Guest house rentals Overstrand Local Municipality
- Beachfront rentals Overstrand Local Municipality
- Waterfront rentals Overstrand Local Municipality
- Villa rentals Overstrand Local Municipality
- Flat rentals Overstrand Local Municipality
- Rentals with a hot tub Overstrand Local Municipality
- House rentals Overstrand Local Municipality
- Rentals with a washing machine and dryer Overstrand Local Municipality
- Pet-friendly rentals Overstrand Local Municipality
- Family-friendly rentals Overstrand Local Municipality
- Cabin rentals Overstrand Local Municipality
- Tiny house rentals Overstrand Local Municipality
- Rentals with pools Overberg District Municipality
- Rentals with pools Western Cape
- Rentals with pools South Africa
- Boulders Beach
- Stellenbosch University
- Babylonstoren
- Grotto Beach (Blue Flag)
- Jonkershoek Nature Reserve
- Cavalli Estate
- Greenways Golf Estate
- Waterkloof Wine Tasting Lounge
- Fernkloof Nature Reserve
- Idiom Restaurant & Idiom Wine Tasting Centre
- Rust en Vrede Wine Estate
- Voëlklip Beach
- Boschendal Wine Estate
- La Motte Wine Farm & Restaurant
- De Zalze Golf Club
- Haute Cabrière - the home of Pierre Jourdan
- Delaire Graff Estate
- Babylonstoren Wine Estate
- Tokara Wine Estate
- De Hollandsche Molen
- Somerset Mall
- Kogelberg Nature Reserve
- Hermanus Beach Club
- Stark-Condé Wines





