Family-friendly holiday rentals in Pearly Beach

4.91 out of 5 average rating, 142 reviews

A spacious deck features a dining table beneath a large umbrella, overlooking the ocean. Soft sunlight casts a warm glow on the tile flooring, while a decorative candle holder and a stack of books add subtle details to the inviting outdoor space facing the sea.

Home in Gansbaai

Ons C-Huis: Gansbaai Seafront Accommodation

This beautifully renovated seafront holiday house is situated between Gansbaai and De Kelders in the Overberg region of the Western Cape. Overlooking Walker Bay, the generous elevated deck allows for the best seaview and up close whale watching opportunities from August to November each year. There are two barbeque (braai ) areas, indoors and outdoors on the seaview deck. Enjoy uninterrupted seaviews from the lounge and wake-up to the soothing sounds of the ocean in the two seafront bedrooms.

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 173 reviews

Home in Stanford

Ferrybridge river house

FERRYBRIDGE HOUSE Loadshedding proof • pet friendly • family friendly • remote work friendly • ideal for birdwatchers • not available over public holiday weekends, Christmas and New Years. Located right on the river with sweeping views, our beloved family holiday home is ideal for family getaways, gatherings with friends, business retreats, and quiet weekends away. Please note we don’t accommodate parties, and only accept guests over 25 years of age, with prior reviews and a 4.5+ rating.

FamilyKitchenQuiet

4.85 out of 5 average rating, 277 reviews

Home in Pearly Beach

Beachfront Home overlooking Ocean

A safe, secluded beachfront house sleeping up to 6 persons. Enjoy the ocean from each room. Breathtaking sunsets over the ocean. Long walks on the beach across the road. One of the best-situated properties in Pearly Beach. Across the prestigious Blue flag status beach, Castle Beach. "Blue Flag Status" is an eco-label for beaches recognized as a trusted symbol of clean quality, environmental awareness, and environmental practices. Cleaned according to AirBnB's C-19 Enhanced Cleaning Protocol.

Indoor spacesKitchenCleanliness

4.99 out of 5 average rating, 110 reviews

A spacious bedroom features a canopied bed draped in soft fabric, complemented by natural wooden accents. A vintage-style bathtub is positioned nearby, and a small wooden table with a chair is visible. Large windows allow natural light to illuminate the earthy tones of the interior.

Earthen home in Stanford

Vineyard Cottage | Goodluck Homestead

Off-grid eco cottage situated on a working regenerative farm in the heart of the Overberg, with panoramic views towards Walker Bay and the Kleinriviersberg mountains. Surrounded by fynbos and vineyards, this cottage has pure spring fed water, a wood fired hot tub, solar power so is not affected by load shedding. Guests are welcome to wander around the farm, swim and fish in the dams, and meander through the veggie gardens We regret no babies, children or pets are allowed for safety reasons.

Indoor spacesKitchenHiking

4.99 out of 5 average rating, 268 reviews

The garden cottage is framed by neatly manicured greenery, with a sparkling swimming pool in the foreground. Sun loungers and an umbrella provide shaded seating. Large glass doors open to a spacious patio area, enhancing the connection between indoor and outdoor living.

Guesthouse in Hermanus

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.

KitchenFamilyBathroom

4.94 out of 5 average rating, 144 reviews

The villa is situated on a hillside surrounded by lush greenery, offering expansive ocean views. Its architectural design features a thatched roof and spacious deck area, which includes a private pool. The surrounding landscape creates a serene coastal atmosphere.

Home in De Kelders

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.

FamilyKitchenCheck-in

4.92 out of 5 average rating, 182 reviews

The exterior of the homestead is showcased, featuring a thatched roof and whitewashed walls set against lush green lawns and trees. A pathway leads to the entrance, surrounded by manicured gardens that enhance the serene atmosphere of the property.

Farm stay in Stanford

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!

Indoor spacesFamilyComfort

4.93 out of 5 average rating, 119 reviews

An aerial view showcases a cottage beside a small dam, surrounded by lush vegetation. The cottage features a simple, functional design with a light-colored exterior. A kayak is visible on the water, complementing the serene landscape of greenery and reflective water.

Farm stay in Gansbaai

Fountainbush Cottage @ Amàre (Stanford/Gans Bay)

Fountainbush cottage is a self catering, eco friendly, family farm stay situated between Stanford and Gansbaai. The cottage is very safe and private overlooking a small farm dam, with horses and sheep wandering past your front gate. Our animals are all tame and your children can get up close and personal with mini pigs, chickens, sheep, horses and dogs. The cottage is well stocked with books, board games, a dress up basket for kids and everything a family needs to relax.

FamilyIndoor spacesGetting around

4.91 out of 5 average rating, 146 reviews

The outdoor pool area features a rectangular pool surrounded by a wooden deck and lounge chairs. A fenced lawn area offers a view of the distant mountains and ocean under a clear blue sky.

Holiday home in Gansbaai

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 (each sleeps 4). 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 available.

FamilyIndoor spacesLayout

4.96 out of 5 average rating, 407 reviews

A small bird with bright yellow-green plumage is perched above its nest, surrounded by vibrant green foliage. Two chicks with open beaks can be seen in the nest, nestled within soft twigs and leaves, awaiting nourishment from their parent.

Guest suite in Stanford

Studio suite, kingsize bed, private garden

Escape to a wonderland of rural tranquility. The Bird House is perfect for a weekend getaway, Garden Route stopover or longer stay for touring the Overberg-Hermanus area. Nestled in its own private garden, the stylish suite offers a well-equipped kitchenette, cosy seating & table for eating/work. Relax in the private bird-filled garden, enjoy a braai & experience starlight quiet. Convenient proximity to wedding venues, wine & cheese farms & places for fine food.

KitchenFamilyNearby

Farm stay in Baardskeerdersbos

Mini House Fynbos at SURYA - Nature Estate

Wake to wide views, fynbos hills, and the slow rhythm of the farm. FYNBOS is for those who want space to breathe — and a warm, off-grid sanctuary when the rest of the world feels stormy. Modern Mini House on a beautiful lifestyle farm with stunning views into the valley. 30 min walking distance to the quaint little village Baardskeerdersbos,

Indoor spacesKitchenWalkability

4.94 out of 5 average rating, 123 reviews

Cottage in Overstrand Local Municipality

COSY Kaleidoscope cottage, near beach and trials

Welcome to freestanding Kaleidoscope Cottage, nestled among the Hibiscus trees with a private varandah overlooking a 25 m pool. It is part of Wil Ahhh - a private property, 5minutes from Grotto Beach. It is designed to celebrate the outdoor lifestyle of Voëlklip, the beach suburb of Hermanus and its beautiful sea and mountain landscape.

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 253 reviews

Popular amenities for Pearly Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Shipping container in Baardskeerdersbos

An aerial view showcases a secluded eco cabin nestled on the mountainside, surrounded by open fields and trees. A winding gravel path leads to the cabin, which features a tent-like structure over an outdoor area. The sun sets behind distant hills, casting a warm light.

Fijnbox eco-cabin

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 130 reviews

Farm stay in Baardskeerdersbos

A cozy cottage stands against a backdrop of rolling hills, featuring a spacious porch with wooden beams. Green grass surrounds the cottage, complemented by vibrant fynbos and protea plants. Large windows allow natural light to enhance the inviting exterior.

Concordia Dam Cottage

KitchenIndoor spacesOutdoor spaces

4.85 out of 5 average rating, 166 reviews

4.98 out of 5 average rating, 142 reviews

Cottage in Sandbaai

Cosy Seaside Cottage | Hot Tub & Fire Pit

FamilyIndoor spacesQuiet

4.88 out of 5 average rating, 201 reviews

A charming house is viewed from an inviting garden filled with vibrant flowers. A covered verandah, furnished for relaxation, extends along the front. Lush green grass surrounds the property, enhancing its tranquil outdoor appeal, while the distant hills provide a serene backdrop.

Home in Hermanus

Veranda House

FamilyIndoor spacesBathroom

4.98 out of 5 average rating, 121 reviews

A scenic view of the surrounding mountains and lush landscapes is presented, featuring tall trees in the foreground and a range of hills in the distance. Soft clouds hover above the peaks, with a clear blue sky providing a serene backdrop.

Farm stay in Hermanus

Great escape with breathtaking view

Indoor spacesKitchenCondition

4.95 out of 5 average rating, 167 reviews

An outdoor area features a hexagonal hot tub surrounded by grassy space. A picnic table with benches is positioned beneath a large umbrella, while a braai area with a grill stands nearby, offering a scenic view of the surrounding landscape.

Cottage in Caledon

Treyntjes River Cottages

FamilyKitchenTV

4.94 out of 5 average rating, 185 reviews

Modern large cottage with Hot Tub, (-Flora studio)

FamilyKitchenHospitality

Cabin in Overstrand Local Municipality

A modern white cabin is positioned against a backdrop of rolling mountains and expansive grasslands, showcasing simple architectural lines. Large windows allow for natural light to fill the interior, and a peaceful outdoor area offers views of the surrounding landscape.

Thuúla Hidden Haven

KitchenFamilyNearby

4.96 out of 5 average rating, 95 reviews

Family- and pet-friendly home rentals

4.8 out of 5 average rating, 125 reviews

A covered deck area features three lounge chairs arranged on a wooden floor. A stone braai unit is visible in the background, offering a space for outdoor cooking. A large window allows natural light to fill the area.

Home in De Kelders

The Beach House

KitchenIndoor spacesOutdoor spaces

4.78 out of 5 average rating, 152 reviews

A picturesque farmhouse is surrounded by lush green fields and gentle hills, with the Akkedisberg mountains rising in the background. The structure features a classic design, with a green roof and multiple sections, nestled among trees and open space.

Farm stay in Stanford

Boskloof Farm Escape

Indoor spacesKitchenHiking

Home in Overstrand Local Municipality

A person with long hair stands barefoot on a wooden deck beside a turquoise pool, holding a glass of wine. Striped towels and a hat are hung on the wall, enhancing the relaxed ambiance.

5 Bed Beach Bungalow w/ pool, fire-pit & solar

Indoor spacesKitchenOutdoor spaces

4.9 out of 5 average rating, 135 reviews

4.87 out of 5 average rating, 108 reviews

The coastal cottage is present at night, with warm light glowing from its windows. A pergola extends over the entrance, and the inviting pool reflects the surroundings. Lush greenery and potted plants frame the scene, contributing to a tranquil outdoor atmosphere.

Cottage in Hermanus

Eastcliff cottage with pool, garden & solar power.

KitchenIndoor spacesLong stay

4.85 out of 5 average rating, 148 reviews

An outdoor seating area is depicted with white wooden chairs arranged around a small table. Large glass doors open to a spacious interior featuring a dining table and comfy lounge. Natural light floods the space, emphasizing the connection between indoor and outdoor living.

Villa in Onrus

Breathe Cottage

FamilyKitchenParks

Cottage in Overstrand Local Municipality

The cottage is surrounded by a lush green lawn and tall trees, showcasing a two-story structure with a sloped roof and multiple windows. A spacious porch extends along the front, inviting relaxation and views of the garden.

Charming cottage in the Hemel & Aarde Wine Valley

Indoor spacesKitchenHeating

4.85 out of 5 average rating, 145 reviews

4.91 out of 5 average rating, 184 reviews

Home in Hermanus

House Vos, luxury family holiday home

FamilyKitchenAmenities

4.94 out of 5 average rating, 127 reviews

Soft sunlight filters through trees, illuminating the outdoor space. A spacious dining table is positioned underneath a covered patio, adorned with decorative candles and a small potted plant. The manicured garden surrounds the area, creating a serene and inviting environment.

Home in Hermanus

Perfect Luxury Holiday Home with Sophistication

KitchenFamilyCleanliness

Family-friendly home rentals with a pool

Guest suite in Overstrand Local Municipality

A tranquil garden is framed by lush greenery and colorful flowering plants, leading to views of the ocean in the distance. The edge of a pristine pool is visible, reflecting the clear blue sky above.

House Atlantic

Indoor spacesFamilyAccess

4.89 out of 5 average rating, 172 reviews

4.94 out of 5 average rating, 106 reviews

The image showcases the exterior of a rondawel with a thatched roof, featuring a circular design and large windows. A stone patio leads to a separate building, which includes large boat-house doors, with views of the tranquil lily pond and surrounding greenery in the background.

Tiny home

Fynbos Paradise

Indoor spacesKitchenAccuracy

Cabin in Overstrand Local Municipality

Flamingo Lake Cabin near Hermanus & Beaches

FamilyKitchenWi-Fi

4.92 out of 5 average rating, 209 reviews

4.89 out of 5 average rating, 226 reviews

Condo in Hermanus

Cliff Path Cottage

Indoor spacesKitchenAccuracy

Guest suite in Overstrand Local Municipality

A spacious outdoor area features a swimming pool surrounded by sunloungers and umbrellas. The stylish two-story cottage is framed by a backdrop of rugged mountains and lush greenery, creating a serene outdoor atmosphere for relaxation.

PROTEA Loft Cottage @ Grotto Beach

KitchenIndoor spacesPool

4.9 out of 5 average rating, 120 reviews

A small balcony features a round table with a yellow mug and a jar. Two wooden chairs are nearby, and a blanket is draped over one. The scene includes a view of the sea through a wide opening, enhancing the relaxing atmosphere.

4.95 out of 5 average rating, 555 reviews

Westcliff Balcony Room

KitchenIndoor spacesView

A spacious living area features a large flat-screen television on a wooden console. A cozy brown ottoman complements the room. Floor-to-ceiling glass doors provide a view of the ocean, while a small outdoor table is seen on the balcony. Soft natural light filters through the curtains.

4.89 out of 5 average rating, 137 reviews

Sea view apartment in Whale Rock Estate Hermanus.

KitchenFamilyGetting around

A balcony is visible, featuring two wooden chairs facing the ocean. The view highlights expansive blue water and distant landforms, with a clear sky above. The glass door allows natural light to create a bright and open atmosphere within the apartment.