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Holiday rentals in Cuenca del Guadarrama

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Top-rated holiday rentals in Cuenca del Guadarrama

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the house is constructed from stone and wood, featuring a large porch with comfortable seating. Lush greenery surrounds the property, while the upper balcony offers views of the garden below. A prominent stone chimney adds character to the inviting façade.
Cottage in Cerro Matallera
4.91 out of 5 average rating, 150 reviews

Casa Matallera - Mountain Retreat near Madrid

Beautiful house in Sierra de la Cabrera Guadarrama, 40 minutes from Madrid. Hiking, cycling, horse riding, leisure activities for families & a varied gastronomic offer. The loveliest municipal pool is just 10 km away. Very quiet area, ideal for disconnecting, resting, or working remotely. Large dining room, living room. Amazing fireplace and very well-equipped kitchen. Ideal for family gatherings, reduced weddings (30/40 pax) in spring and autumn (events subject to small extra payment to agree).

Top guest favourite
Flat in Fuente el Saz de Jarama
4.96 out of 5 average rating, 140 reviews

Sweet and cozy apartment

Relájate y desconecta en este apartamento tranquilo y elegante.Primeras calidades y nuevo,completo para todas tus necesidades. Entrada independiente al estudio directa desde la calle. Este alojamiento se encuentra a 15 minutos del AEROPUERTO y CIRCUITO JARAMA, 20 minutos IFEMA y centro de Madrid .Si buscas un poco de ocio o algo para comer,a menos de cinco minutos andando esta la zona de los bares y supermercados Día y Mercadona.Aparcamiento en la misma puerta sin necesidad de buscar.

Top guest favourite
Flat in San Sebastián de los Reyes
4.98 out of 5 average rating, 209 reviews

Madrid´s sky Luxury Penthouse 6Pax. 10 min Airport

Madrid´s Sky Luxury Penthouse 6pax. Airport Just 10 Minutes from Madrid Barajas AIRPORT in MADRID Designed for 2/3/4/5/6 People. Discover a duplex that redefines luxury in MADRID! This amazing space combines avant-garde design with dazzling lighting. From the first moment, the infinity effect of the views will take your breath away, creating a magical connection with the horizon. Every corner radiates elegance and sophistication. A visual experience that will captivate you!

Guest favourite
Flat in San Sebastián de los Reyes
4.93 out of 5 average rating, 135 reviews

Family Room on Lower Ground Floor at Casa Caliche

Enjoy a private family room (two bedrooms, living room and more) with its own bathroom in a peaceful villa surrounded by nature, just 20–30 minutes from Plaza de Castilla and 15–25 minutes from Madrid Airport. A place to rest, work remotely, or disconnect while staying close to the city. ✔ Fast WiFi + dedicated workspace ✔ Saltwater swimming pool (open year-round) ✔ Garden, BBQ and terraces with mountain views ✔ Free parking inside the property ✔ Quiet & relaxing atmosphere

Guest favourite
A modern bathroom features a freestanding white tub and a glass shower. Natural light enters through a round window, highlighting the smooth, neutral wall textures. A small wooden table holds two glasses, a bottle of wine, and a candle, adding a subtle touch of elegance.
Home in Madrid
4.95 out of 5 average rating, 113 reviews

Dreamy treehouse

Discover the magic of this charming wooden house, an oasis of tranquility surrounded by trees and nature. Its unique design integrates modernity with the natural environment. Here, you will wake up to the sound of birds and the breeze through the trees, enjoying a cozy and sophisticated atmosphere. A few meters away, you will find hiking trails that cross landscapes where you can see horses, bulls and the beauty of the countryside. Perfect for disconnecting and relaxing.

Guest favourite
Cottage in Miraflores de la Sierra
4.91 out of 5 average rating, 315 reviews

Amazing garden and charming villa in the mountains

A beautiful renovated house from the 60s on a large 1500m plot with a private pool and large trees. Tranquility and privacy in the heart of the forest in one of the most beautiful villages in the Sierra de Madrid. You can walk for days through the forests and mountains of Guadarrama National Park from your doorstep. Great for two families to share. Totally charmingly equipped. Fireplace, gas BBQ, ping-pong, trampoline, slide, basketball basket, Wi-Fi, and more

Top guest favourite
Loft in San Sebastián de los Reyes
4.92 out of 5 average rating, 606 reviews

Amazing Views, Parking and Close to the Airport

ELEGANT LOFT WITH SPECTACULAR VIEWS. 10 minutes from MADRID AIRPORT. The luck of seeing everything from a unique perspective. Enjoying the light and views of this loft is a pleasure within your reach. Relaxing in it is finding the balance between details and simplicity in a unique atmosphere. Free Parking Rooftop pool in the summer months. 📌License number: VT-4679 📌Single Rental Registration: ESFCTU000028054000654561000000000000000000000VT-46793

Top guest favourite
A rustic stone house is positioned amid a natural landscape, featuring a wooden staircase leading to the entrance. Lush greenery surrounds the property, with expansive views of the mountains in the background under a clear blue sky.
Chalet in El Boalo
4.99 out of 5 average rating, 158 reviews

Beautiful rustic house in the mountains of Madrid

Very comfortable rustic house located in the heart of the "Sierra de la Pedriza", that belongs to the Guadarrama regional park, and just half an hour from Madrid. The land of this house has an area of ​​3000 square meters with natural vegetation in the area. 5 minutes walk you will find the beautiful town "El Boalo". Impressive views of the Sierra de Madrid. Possibility of beautiful excursions, horse riding and multiple activities.

Top guest favourite
A spacious living area features light wood flooring and soft overhead lighting, complemented by modern furniture. A comfortable sofa is positioned adjacent to a wall-mounted television. Decorative plants add a touch of greenery, while a stylish lamp stands beside a dining area with two chairs.
Holiday home in Alcalá de Henares
4.97 out of 5 average rating, 111 reviews

Luxury Suite in Libreros I Large Living Room I Balcony

Disfruta de este exclusivo refugio, reformado en febrero de 2025. Con vistas a la emblemática calle Libreros, su diseño sofisticado lo convierte en el lugar ideal para parejas que buscan una escapada inolvidable, nomadas digitales y pequeñas familias. Rodeados de los mejores restaurantes y comercios, viviréis la historia de la ciudad con el máximo confort moderno. ¿Listos para una estancia mágica? ¡Reservad vuestras fechas ahora!

Guest favourite
A wooden house with a welcoming porch is surrounded by lush greenery. Potted plants adorn the porch, while the stone wall and textured pathway complement the natural setting. Large windows provide ample light, enhancing the connection between the indoor and outdoor spaces.
Cabin in Uceda
4.88 out of 5 average rating, 552 reviews

Miguel's Cabin

Cozy wooden house with fireplace and 2700 Mt of wooded plot, fully fenced and private. Ideal for city getaways, enjoying nature, clean air and tranquility, 45 min from downtown Madrid. In a sparsely populated development in the municipality of Uceda, Guadalajara (400 meters bordering the community of Madrid). Near Patones de Arriba, Atazar, Jarama River.

Guest favourite
An open-concept loft features a modern living area with a gray sofa and unique coffee tables. A sleek kitchen with a breakfast bar is visible in the background. Stairs lead to a second level, adorned with artwork and large windows, highlighting the contemporary design.
Flat in Aeropuerto
4.88 out of 5 average rating, 570 reviews

Designer loft in Barajas

Cozy loft in historic Barajas, just minutes from the metro with direct links to the airport, IFEMA, and city center. Cozy loft in historic Barajas, just minutes from the metro with direct links to the airport, IFEMA, and city center. Cozy loft in historic Barajas, just minutes from the metro with direct links to the airport, IFEMA, and city center.

Top guest favourite
Farm stay in Braojos
4.95 out of 5 average rating, 163 reviews

Via Fera, with views of nature

Isolated rural space with capacity for 2/3 people, with a 1,000 square meter wild garden and a gazebo over the Lozoya river valley. Located in an old cattle farm. Kilometers of horizon over a score of towns in the Madrid mountains.

Popular amenities for Cuenca del Guadarrama holiday rentals

  1. Airbnb
  2. Spain
  3. Madrid
  4. Cuenca del Guadarrama