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Holiday rentals with a pool in Cape Winelands District Municipality

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Top-rated rentals with a pool in Cape Winelands District Municipality

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view captures the villa's spacious garden and the inviting pool area, framed by lush greenery. The surrounding landscape features majestic mountains and valleys, creating a serene backdrop. Solar panels on the roof contribute to the sustainable features of the home.
Villa in Franschhoek

VillaFortyTwo - quiet & spacious. Sleeps 4-10.

This hidden gem is situated in the centre of Franschhoek within walking distance of shops, market, galleries and superb restaurants. It's the ideal place to escape to, year-round, with family and friends. This lovely and very spacious solar-powered family home offers a large garden with magnificent views from the veranda, a 15m pool at the Poolhouse and enough fireplaces🔥🔥to keep you warm in winter. For outdoor sports & nature lovers, our "backyard" has abundant trails for hiking and cycling.

LocationFamilyWalkability

4.95 out of 5 average rating, 149 reviews
Top Guest favourite
A stone cottage is set against a dramatic sky, surrounded by rugged rocks and a landscape of rolling hills. The outdoor patio is visible, providing a space for relaxation. Clouds drift lazily, creating a serene atmosphere in the secluded location.
Home in Cape Winelands District Municipality

Peace and Quiet Stone Cottages

Rust en Vrede means rest and peace in Afrikaans which describes the experience of staying in these these two stone cottages. They are 20m apart and are ONLY offered as a pair, and have exclusive use of a rock pool. Each cottage has two 3/4 beds, bathroom, kitchenette and patio. The pair of cottages accommodate a MAX of 4 people in TOTAL in a private setting, with expansive views. These new cottages are in the same format as the other four on the farm which have received hundreds of 5* reviews.

ValueLocationPool

4.98 out of 5 average rating, 105 reviews
Top Guest favourite
A sprawling outdoor area is showcased with lush greenery and desert landscaping. A covered patio with stone pillars is visible, along with rustic seating arrangements. In the foreground, a lap pool glistens under the sun, framed by natural elements and mountains in the background.
Home

SUGARBIRD HOUSE EDENVELDT FARM

I have decided to rent out my personal farm house\ guest house to happy road trippers seeking solitude and a peaceful surrounding. The house is within a valley surrounded by 48 hectares of open land,beautiful mountain (cederberg) backdrops and a river with three natural swimming areas within walking distance of the guest house and the place include a 25m lap pool right in front of the veranda! Oh and plenty of clean breathable air :). There is one full sized bed so its best suited for couples.

LocationFamilyBarbecue

4.97 out of 5 average rating, 407 reviews
Top Guest favourite
A serene outdoor area is showcased with a rim flow pool surrounded by manicured grass and blooming lavender. A large umbrella provides shade over two loungers, while rolling hills and vineyards create a scenic backdrop under a clear blue sky.
Cottage in Franschhoek

Blueberry Hill Cottages - Lavender - Franschhoek

Lavender Cottage is a modern three bedroom self catering cottage with three bedrooms, main ensuite and the other two bedrooms share a full bathroom. There is a fully equipped kitchen with cooker, microwave and Nespresso coffee maker. The cottage has its own private terrace overlooking the large rim flow pool. The pool is situated on it's own large terrace and is shared with Olive cottage. We are ideal for guests who enjoy wine tours, the outdoors, hiking and biking plus horse riding.

ValueFamilyHospitality

4.87 out of 5 average rating, 317 reviews
Top Guest favourite
The open-plan lounge and dining area features a central wooden table surrounded by classic chairs. A cozy seating arrangement with woven chairs sits beside a rustic broom. Light enters through windowpanes, illuminating the clay-tiled floor and highlighting the textural elements of the thatched-roof interior.
Cottage in Greyton

Potato Patch Self Catering Cottage

This versatile thatched roofed cottage is centrally located in a private setting offering contemporary country comfort with a dash of history. It is one of the two cottages located on the owners property with its own entrance and secluded garden. The cottage consists of 3 en suite bedrooms furnished with king sized beds. The rates are based on 2 people sharing a room. Using additional rooms comes with an additional charge. Pets are permitted on request at an additional charge.

LocationFamilyBackyard

4.87 out of 5 average rating, 297 reviews
Top Guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality

Heidi's Barn, Franschhoek

Situated on a small holding 5km outside Franschhoek, opposite the exquisite La Motte Wine Estate, Heidi’s Barn offers the perfect self-catering base from which to explore the Winelands. A fire pit, outdoor dining area and a large swimming pool (shared with one other cottage) are perfect for summertime relaxation while an indoor wood-burning fireplace and wooden floors throughout make for a cosy winter escape. The barn runs on mains power with solar back up for load shedding.

LocationValueSleep quality

4.99 out of 5 average rating, 176 reviews
Top Guest favourite
A quaint cottage is enveloped by lush vines, with a welcoming front porch featuring two chairs. The roof is made of metal, and wooden doors and windows complement the natural surroundings. Soft light accents the stone pathway leading to the entrance.
Cottage in Wellington

Vineyard Cottage at Bosman Wines

A serene, beautifully styled cottage with layered textures, soft neutral tones, and thoughtful finishes throughout. It features a cosy lounge, a well-appointed kitchen, and a dreamy en-suite bedroom designed for restful comfort. Set on the 8th generation Bosman Family Vineyards, the cottage offers sweeping vineyard views and an authentic sense of countryside living. A scenic 10-minute walk leads to the cellar, where a complimentary tasting awaits.

ValueFamilyLong stay

4.97 out of 5 average rating, 230 reviews
Guest favourite
An open-plan living room is furnished with a comfortable couch and decorated with cushions. Large glass doors provide views of the outdoor area, which features a dining set on the stoep. Natural light enhances the airy ambiance, complemented by wooden beams on the ceiling.
Farm stay in Worcester

Vineyard House

30km outside Worcester (towards Villiersdorp) The perfect romantic getaway in beautiful and tranquil surroundings. Vineyard House is surrounded by a 360° view of vineyards and mountains. We offer a modern, private stay just outside Worcester, approximately 1½ hours drive from Cape Town. Vineyard House offer a 2 bedroom house (sleeps 4), a bathroom, fully furnished kitchen, livingroom with a fire place and a stoep looking onto the vineyards.

FamilyLocationNearby

4.96 out of 5 average rating, 331 reviews
Top Guest favourite
A spacious living area is featured with large glass panels offering views of the mountains and sea. A comfortable sofa and armchair are arranged around a coffee table. A dining table is set for four, complemented by decorative plants and fresh flowers.
Apartment in Somerset West

Luxury apartment Kandinsky with panoramic views

High-quality luxury apartment for 2 people in Somerset West, prime location. 10 m long panoramic glass front overlooking mountains and sea. The apartment has a living area with kitchen, bathroom and one bedroom. A Nespresso machine, toaster, kettle, hair dryer, towels and linens are available. Extra long king size bed and TV. Pool and outdoor area are available for shared use and sauna and jacuzzi can also be offered by arrangement.

ValueFamilyDecor

4.99 out of 5 average rating, 182 reviews
Top Guest favourite
A wide opening reveals a scenic view of the mountains. An outdoor seating area is situated beside a tranquil eco pool, adorned with colorful plants. A dining table with a simple white tablecloth is positioned indoors, with an orchid centerpiece adding a touch of elegance.
Home

Dassieshoek - Or Skool

Situated in the mountains of Robertson, this double volume, beautifully restored Old School is a tranquil getaway for the whole family. There is a gorgeous eco pool and plenty of amenities for children. Located next to the Marloth Nature Reserve, the house is at the beginning of the Arangieskop Hiking Trail. Mountain biking, hiking, birding and river and dam access mean that there are plenty of outdoor activities for the whole family.

ValueFamilySleep quality

4.96 out of 5 average rating, 195 reviews
Top Guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch

Romantic cottage with a pool AND an open air tub!

RiverStone Cottage lies at the foot of the majestic Simonsberg mountain with panoramic views in all directions. Whether you are relaxing under vast oaks or at the plunge pool and watching the sunset turn the mountains pink or are an early bird and watching the sun rise behind cheeky, pointed Botmanskop, there are moments aplenty to ooh and aah at the majesty that surrounds this very special place.

ValueLocationAir conditioning

4.98 out of 5 average rating, 531 reviews
Guest favourite
Home in Franschhoek

Newly renovated, dreamy 3 bedroom house with Solar

Enjoy a beautiful artistic home full of character and carefully curated interiors. Don’t worry about loadshedding with the solar and inverter system. All rooms have en-suite bathrooms. The main bedroom has a super king bed, the second room has a queen bed and the third room has a 3/4 bed as well as a bunk bed (2 singles) We really love catering to easy-going guests.

LocationValueCondition

4.96 out of 5 average rating, 172 reviews

Popular amenities for Cape Winelands District Municipality rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
An open-plan living area features wooden beams and brick walls, with a spacious dining table surrounded by upholstered chairs. Natural light floods the space through large windows, highlighting the relaxed atmosphere. A staircase leads to a loft area, and a view of the pool can be seen outside.
Home in Franschhoek

Nooks Pied-a-Terre | Architecturally Stunning Home

FamilyLocationParking

4.92 out of 5 average rating, 156 reviews
Guest favourite
A spacious dining area features a large wooden table surrounded by metal chairs. The kitchen island is designed with a sleek white finish and includes modern appliances. Natural light floods the space through expansive glass doors that open to a green outdoor area.
Home in Greyton

Contemporary Barn style house

FamilyLocationAccess

4.86 out of 5 average rating, 249 reviews
Guest favourite
Home in Stellenbosch

Bellevlei Estate | The Rock House

FamilyLocationComfort

4.89 out of 5 average rating, 111 reviews
Guest favourite
Home in Wolseley

Trendy private container home! Riverstone House.

FamilyLocationBiking

4.94 out of 5 average rating, 123 reviews
Guest favourite
A scenic dirt road leads towards majestic mountains, framed by greenery. A group of children, accompanied by an adult, can be seen walking together down the path. The sky is partly cloudy, adding a touch of brightness to the landscape.
Home in Prince Alfred Hamlet

Spacious Elandsrivier Farmhouse

ValueFamilyAccuracy

4.95 out of 5 average rating, 115 reviews
Guest favourite
An outdoor area is framed by lush greenery, featuring a wooden pergola with seating. A swimming pool is visible in the background, surrounded by well-maintained plants. The natural light creates a serene atmosphere, inviting relaxation in the garden space.
Home in Swellendam

Exclusive Poolside Cottage in Prime Location

ValueFamilyHiking

4.91 out of 5 average rating, 528 reviews
Top Guest favourite
A spacious living area features a large sectional sofa and a stylish coffee table. A fireplace is positioned under a mantle, while a wide window offers views of the outdoors. Natural light filters through sheer curtains, creating a bright and comfortable setting.
Home in Franschhoek

Camphor House

ValueFamilyPool

4.97 out of 5 average rating, 111 reviews
Guest favourite
A spacious bedroom features a large bed with soft linens and light blue accents. The room is complemented by built-in cabinetry and a stylish red desk. Natural light filters through two windows, and a decorative chandelier enhances the ceiling's wood texture.
Home in Franschhoek

Luxury 2 bed Villa & pool, Sandstone, Franschhoek

LocationValueComfort

4.94 out of 5 average rating, 112 reviews

Condo rentals with a pool

Guest favourite
The spacious bedroom features a thatched roof with wooden beams, a large bed dressed in crisp linen, and a decorative throw. Natural light floods the room through large windows, illuminating a small desk and seating area. A cozy rug enhances the warm atmosphere.
Condo in Paarl

Shades of Africa - The Studio

FamilyLocationPets

4.87 out of 5 average rating, 255 reviews
Guest favourite
A contemporary studio apartment showcases a spacious bed with dark green decorative pillows. A compact kitchen is visible in the background, along with a dining table and chairs. Towels are neatly arranged on the bed, enhancing the clean and organized appearance of the space.
Condo in Stellenbosch

Unique Stay at The Den Stellenbosch

LocationValueComfort

4.99 out of 5 average rating, 103 reviews
Guest favourite
A spacious outdoor swimming pool is surrounded by lounge chairs and bordered by neatly landscaped greenery. The complex features modern buildings, with large windows that allow natural light to brighten the shared spaces. A tranquil atmosphere is created by the combination of water and greenery.
Condo in Cape Town

J Spot • Safe & Convenient • Backup Power

LocationValueGetting around

4.93 out of 5 average rating, 123 reviews
Guest favourite
Condo in Johannesdal

Villa Verde, farm stay with views for days.

FamilyLocationCleanliness

5.0 out of 5 average rating, 24 reviews
Top Guest favourite
Condo in Stellenbosch

Avemore Vineyard View

ValueFamilyNearby

4.88 out of 5 average rating, 88 reviews
Top Guest favourite
A welcoming living area is designed with a plush couch and a flat-screen television mounted on a unit with wood accents. Large windows allow natural light to enter, offering views of greenery. A bookshelf is filled with various volumes, enhancing the cozy ambiance.
Condo in Cape Town

Serenity Haven - Two Bedroom

FamilyLocationPool

5.0 out of 5 average rating, 23 reviews
Superhost
Condo in Breede River District

Gemsbok House - Drie Kuilen Nature Reserve

FamilyValueBarbecue

4.86 out of 5 average rating, 7 reviews
Top Guest favourite
The outdoor space features a sparkling pool surrounded by lush greenery and a patio area. The house, with warm-toned brick walls, offers a spacious deck with seating. Palm trees and garden plants create a serene atmosphere, highlighting the inviting environment during twilight.
Condo in Somerset West

Thyme Out - Private Apartment

ValueLocationQuiet

4.91 out of 5 average rating, 81 reviews

Other holiday rentals with a pool

Guest favourite
A scenic view showcases Obiekwa Country House surrounded by a well-established indigenous garden. The property features a covered patio and swimming pool, with mountains providing a tranquil backdrop. The image captures the serene rural setting and proximity to vineyards.
Guesthouse in Riebeek-Kasteel

Obiekwa Country House

LocationFamilySleep quality

4.85 out of 5 average rating, 161 reviews
Guest favourite
An inviting living area features a comfortable gray sofa adorned with decorative pillows. A wooden table holds a vase filled with fresh flowers. Natural light filters in through large windows, illuminating the space beneath vaulted wood-beam ceilings, with a staircase leading to the loft.
Apartment

Off Grid Getaway with Breathtaking Mountain Views

FamilyLocationKitchen

4.88 out of 5 average rating, 658 reviews
Guest favourite
The entrance to the cottage is framed by a serene vine-covered trellis, leading to a cheerful red door. Flanking the path, a mix of local plants and herbs adds vibrant greenery to the welcoming atmosphere.
Cottage in Franschhoek

Gorgeous Cottage in the ❤️ of Town

ValueFamilyWi-Fi

4.85 out of 5 average rating, 346 reviews
Top Guest favourite
A modern double-storey townhouse features a light-colored exterior with a sloped roof. Two small pools are visible in the front yard, alongside a covered dining area. The backdrop consists of scenic mountains, enhancing the serene setting.
Townhouse in Franschhoek

Four Seasons, Franschhoek

LocationValueTV

4.93 out of 5 average rating, 206 reviews
Guest favourite
Villa in McGregor

The FAIRY FLYCATCHER (Lucky Crane Villas)

ValueLocationIndoor spaces

4.95 out of 5 average rating, 168 reviews
Guest favourite
A heated outdoor pool is surrounded by natural stones, with two lounge chairs positioned nearby. Lush greenery and rolling mountains create a stunning backdrop, illuminated by soft sunlight. This serene setting emphasizes the connection to nature and offers a peaceful retreat.
Tiny home in Cape Winelands District Municipality

The Pod Robertson

ValueLocationAmenities

4.9 out of 5 average rating, 262 reviews
Guest favourite
A spacious main room features a comfortable bed with elegant bedding, flanked by two nightstands with lamps. Large windows provide views of the outdoor area. A decorative rug adds warmth to the concrete floor. A stylish seating area is visible in the corner.
Cottage in Worcester

Tango - Luxury Honeymoon Suite with Hot Tub

FamilyLocationComfort

4.94 out of 5 average rating, 118 reviews
Top Guest favourite
A single-story guest house is framed by natural greenery and rugged mountains. The structure features a sloped roof and large windows that invite ample sunlight. Surrounding outdoor spaces are marked by well-maintained plants, offering a serene and open atmosphere.
Farm stay in Clanwilliam

SKILPAD FARM HOUSE EDENVELDT FARM CEDERBERG

ValueLocationGetting around

4.94 out of 5 average rating, 212 reviews

Destinations to explore