Chalet holiday rentals in Sur

5 out of 5 average rating, 26 reviews

A private saltwater pool is framed by wooden decking and equipped with sun loungers. An umbrella provides shade beside the pool, while a light-colored house with large windows is visible in the background, surrounded by trees.

Chalet in Valdemorillo

Family Villa with Private Pool

¡Escápate al campo! Descanso y relax a tan solo 45 minutos de Madrid en coche. Amplia y cómoda casa situada en un entorno tranquilo con piscina privada. Ideal para unas vacaciones aptas para niños: Parque Infantil y Casita en el árbol. Ideal para invitar a amigos y familiares: barbacoa y cenas al aire libre. Destino popular para senderistas. Explora las cercanías de El Escorial y la Sierra de Guadarrama, Ávila, Segovia y San Ildefonso. Parque Acuático Aquopolis a tan solo 15 minutos en coche.

4.98 out of 5 average rating, 99 reviews

Chalet in La Cascabela

Oasis with private pool just steps from downtown!

Enjoy a Premium Experience in Madrid!! 🏡Stay in a beautiful design house with private pool & garden near Madrid Río, just minutes from the historic city center! 2 bedrooms + 2 bathrooms, heated floors, A/C, fast Wi-Fi. 🏊‍♂️ Relax in your private pool (mid-April to early October) or stroll to nearby park & cafés. 🚇 Direct metro to El Rastro, Royal Palace & Gran Vía. Quick access to main attractions! ✨ Perfect for families or friends looking for a stylish, peaceful stay 😉 You Will ❤️ it!!

Chalet in Las Ventas de Retamosa

A rectangular salt-water pool is surrounded by a well-maintained green lawn. Several white lounge chairs are positioned alongside the pool, facing a warm sunset sky punctuated by scattered clouds. A stone wall encloses the area, providing privacy.

4.91 out of 5 average rating, 130 reviews

Family-friendly villa with a pool and garden

Family-friendly villa, 30 minutes from Madrid and 30 minutes from Toledo. It has a swimming pool, garden, barbecue and porch to enjoy outdoor meals, open kitchen with American fridge. It has 4 bedrooms + 3 bathrooms, a basement with beds, a ping pong table, foosball, darts and games. Ideal to get away and have a good time. Close to 2 parks, sports center, country walks, Dia supermarkets. Unide and shops. Close to Puy du Fou, Xanadú Shopping Center. No groups that throw parties

4.92 out of 5 average rating, 65 reviews

A spacious white chalet is shown with a covered terrace on the upper level. Lush greenery and a manicured lawn surround the property, which is complemented by tall trees. Bright blue skies with a few fluffy white clouds fill the background.

Chalet in Torrelodones

Ground floor in a country house

An accommodation in the middle of nature (GROUND FLOOR) To enjoy peace, nature, gastronomy and sports. Have a barbecue or swim in the pool in summer. 5 minutes from a lake with hiking trails IDEAL for climbers: Vías de Torrelodones 5 minutes away and La Pedriza 25 minutes away. YOU CAN park the van inside. Well connected to go to Madrid. Close to the shopping centers of LAS ROZAS, CASINO DE TORRELODONES, the Sierra de Madrid and Toledo, Segovia, Ávila, etc.

An outdoor area is illuminated at night, showcasing stone steps leading to a spa area and a pool. Soft lighting highlights the structure, and surrounding greenery adds to the serene environment.

4.93 out of 5 average rating, 44 reviews

Exclusively for couples

Natural environment between encinas and the Alberche river, just 40 minutes from Madrid. Located in the Urbanización Calalberche, second largest urbanization in Europe. Enjoy our comfortable facilities and exceptional service. •Jacuzzi •Chill area •Pool ( Open from 19-May to 30-Septiembre ) •BBQ Our apartment is designed with a modern twist and offers breathtaking views. (THE ENTIRE VILLA IS FOR A SINGLE RESERVATION, THERE ARE NO COMMON AREAS TO SHARE)

Superhost

A bright living area features a comfortable seating arrangement with a white couch and decorative cushions. A dining table with patterned covers is accompanied by black chairs. Natural light enters through large windows adorned with sheer curtains, contributing to a spacious and airy atmosphere.

Chalet in Colmenar de Oreja

4.66 out of 5 average rating, 319 reviews

Chalet Apt. (Aranjuez/Chinchón/Warner/Madrid)

Chalet consisting of 2 separate floors, single entrances, Valle San Juan urbanization, minutes from Aranjuez, Chinchón, Warner, and Danco Aventura. Quiet part of the Ruta de la Vega, bathed by the Tagus, Jarama and Tajuña rivers. Ideal for leisure and leisure activities, with a varied landscape, perfect for nature lovers in rural areas, hiking such as the Barranco de Villacabras route, the Cueva del Fraile,etc.Air conditioning, outdoor barbecue, crib.

4.87 out of 5 average rating, 92 reviews

A cozy outdoor seating area is presented, featuring a spacious L-shaped sofa arranged around a central glass table. Colorful cushions add comfort, while hanging planters filled with vibrant flowers enhance the ambiance. A pergola provides shade, creating a pleasant space for relaxation.

Chalet in Vaciamadrid

Family Garden Chalet 15 minutes from downtown and Warner

Modern and bright family house of 180 m² with a private garden of 250 m², located in a quiet development in Rivas Vaciamadrid. Ideal for families or groups looking for space, comfort and good connection with Madrid and Warner Located in one of the newest neighborhoods in the city, it is surrounded by greenery, shops and amenities. With bus stop at the gate, nearby metro station, and an environment designed for a comfortable, safe and relaxed stay.

Superhost

Chalet in Soto de Viñuelas

4.78 out of 5 average rating, 23 reviews

Apartment with a bathroom suite

Independent apartment with entrance from the garden of a chalet, Hosts Daniel and Rosa Equipped with room_bedroom with a leather sofa with an electric mobilization system, a folding table with two chairs to eat inside , and a double bed Also a kitchen and large bathroom , perfect for tourists who like the natural without moving away from the cities . Close to the Autónoma, Madrid, Sierra Norte. With private pool, common spaces and parking .

Chalet in San Lorenzo de El Escorial

A two-story chalet is shown, surrounded by greenery. The upper balcony features decorative railings, while outdoor stairs lead to the spacious ground level. A private swimming pool is visible, along with several sun loungers arranged nearby. The backdrop includes mountains under a clear blue sky.

4.86 out of 5 average rating, 65 reviews

SUYOLUCE, villa with private pool *El Escorial*

SUYOLUCE is a beautiful villa located between El Escorial and San Lorenzo de El Escorial. Its location makes it easily accessible from the center of both towns, as well as from some of the area's most outstanding tourist spots, such as the Royal Monastery of San Lorenzo de El Escorial or the Casita del Príncipe, both located about a 10-minute walk from the house. Excellent public transport connections with the 661 bus stop to Madrid at the door.

4.77 out of 5 average rating, 39 reviews

A spacious living area features a large, light-colored sectional sofa arranged around a low coffee table. A modern fireplace is positioned against a white wall, while large windows allow natural light to fill the room. Decorative elements include a floor lamp and a wooden shelving unit.

Chalet in Griñón

Beautiful villa. Enjoy/rest

Beautiful Villa!! Newly renovated (brand new) stylish Perfect for group trips. Large fenced pool for children/BBQ. It has a fireplace and central heating. 30 Mins Madrid and Toledo It has 7 rooms, for 14 people: Four bathrooms. Spacious living room of 50 m2 with fireplace and large TV. 60m2 kitchen with an American bar. Garden with Pool, BBQ Area. Large areas where you can enjoy with family and friends. Parking for 7 cars.

A modern yellow chalet is situated on a hillside, offering panoramic views of the surrounding landscape. Lush greenery and distant mountains can be seen under a partly cloudy sky. The serene environment suggests a peaceful retreat away from urban life.

4.97 out of 5 average rating, 74 reviews

El Mirador de Calalberche Cottage

Beautiful detached chalet with private pool, barbecue and wine cellar, Ideal for your family vacation or getaways with friends. Overlooking the Sierras de Gredos and Guadarrama, in a natural setting in which you can enjoy various activities such as: Safari Park visit, HUMOR. YELLOW, horse riding, hiking, bike trails, etc . Enjoy a getaway on the banks of the Alberche River, of and privacy. THE POOL IS OPEN FROM 12-4-2025

Superhost

Chalet in Villanueva de la Cañada

4.81 out of 5 average rating, 26 reviews

Cozy house Villanueva pool & air conditioning

Enjoy and relax in a great house in and we offer you a free parking space in central Madrid, two minutes from Gran Vía. Close to a La Dehesa golf club, water park, equestrian centers for horse riding and Warner Park 35 minutes away. Villanueva de la Cañada offers supermarkets, shops, services and excellent restaurants. But you can go to Madrid, leave your car and enjoy the city center comfortably.

Popular amenities for Sur chalet rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly chalet rentals

A charming two-story chalet is featured with a sloped roof and wide porch, constructed with brick and wood. Columns support the porch area, where outdoor furniture is set against a backdrop of landscaped greenery.

4.66 out of 5 average rating, 35 reviews

Charming villa

An outdoor view of the chalet showcases a covered seating area and a swimming pool with a blue cover. Surrounding trees provide shade, and outdoor lighting enhances the ambiance. The lawn features artificial grass, contributing to an inviting space for relaxation.

4.97 out of 5 average rating, 95 reviews

The Wooden Whim

Chalet in Robledo de Chavela

5 out of 5 average rating, 10 reviews

Bergidum

A spacious garden area is highlighted by vibrant pink flowers, providing a colorful border. In the center, a rectangular pool is flanked by sun loungers and shaded seating. A gazebo stands in the background, with recreational equipment visible, under a clear blue sky.

4.77 out of 5 average rating, 129 reviews

Rural house apartment with fireplace

A spacious outdoor area features a clear swimming pool surrounded by a tiled patio. A dining set with white chairs and a patterned tablecloth is positioned under a large umbrella. Tropical plants and vibrant flowers add colors to the corner of the garden.

Chalet in Madrid

4.68 out of 5 average rating, 161 reviews

Accommodation with a year-round pool

A spacious outdoor area is shown, featuring a private swimming pool surrounded by a safety fence. Sun loungers are placed near the pool, and a covered barbecue area is visible alongside the house, complemented by ample greenery.

Chalet in Madrid

4.75 out of 5 average rating, 4 reviews

El Aligustre: Enjoy Valdelaguna with a Pool

Large windows provide a view of the lush outdoor landscape, featuring trees and pathways. A cozy seating area is visible with a warm blanket draped over the couch. The space is bright and airy, fostering a connection between indoor comfort and natural surroundings.

Chalet in Dominio de Fontenebro

4.89 out of 5 average rating, 19 reviews

A villa with stunning views

A single-story house sits under a clear blue sky, featuring a covered porch and surrounding open spaces. The large garden area is filled with green grass and shaded by trees, creating a serene environment that invites relaxation.

4.69 out of 5 average rating, 32 reviews

The villa for couples to relax

Luxury chalet rentals

Chalet in El Viso de San Juan

The exterior of the home features a vibrant red facade surrounded by green lawns. A playground slide is visible in the foreground, accompanied by picnic tables and shaded areas. The spacious yard provides an inviting atmosphere with ample room for outdoor activities.

4.96 out of 5 average rating, 25 reviews

House with a pool (up to 12 people) El Viso de San Juan

A three-story chalet with a terracotta roof is surrounded by lush greenery and palm trees. The exterior features a mix of stone and plaster, showcasing large windows. A clear sky provides bright lighting, enhancing the natural setting.

4.78 out of 5 average rating, 164 reviews

Villa Maribel, a 3-story chalet with a pool.

A modern two-story house is framed by a well-maintained lawn. A stone pathway leads to the entrance, bordered by lush greenery. The exterior features a mix of brick and stone, with large windows and a distinctive peaked roof. A driveway and garage are visible on the side.

Chalet in Las Rozas de Madrid

4.71 out of 5 average rating, 31 reviews

Nice Chalet to rest

A modern chalet featuring expansive glass walls is surrounded by lush greenery and landscaped gardens. A tranquil outdoor area includes a uniquely shaped saltwater pool, framed by natural rock formations and shaded by nearby trees, providing a peaceful retreat.

Chalet in Colmenarejo

4.92 out of 5 average rating, 49 reviews

Villa Shela

A swimming pool is framed by a stone terrace, featuring a gentle curve and steps for easy access. In the background, a residential structure with a traditional design is visible, alongside a tower topped with a spire, suggesting a serene setting.

Chalet in Yunclillos

4.86 out of 5 average rating, 29 reviews

Yunclillos Rural House. Casa Dori

A spacious outdoor area features a clear blue swimming pool surrounded by manicured lawns and a variety of trees. Nearby, a sun lounger is placed on a tiled patio, and additional seating can be seen along the grass.

Chalet in Villaviciosa de Odón

4.86 out of 5 average rating, 14 reviews

A villa residence with a large garden and swimming pool

The two-story chalet is constructed with brick, featuring a sloped roof and multiple windows. The property is surrounded by a green fence, with a clear view of nearby street signs indicating the location. A tree-lined street adds to the residential atmosphere.

Chalet in Pozuelo de Alarcón

Single-family home 10 pax madrid aravaca

A clear view of a swimming pool surrounded by a simple fence, with lounge chairs and an umbrella nearby. A small open area features a shaded structure with seating. The surrounding landscape consists of trees and hills, indicating a tranquil setting.