
House holiday rentals in Sierra de Guadarrama
Find and book unique houses on Airbnb
Top-rated house rentals in Sierra de Guadarrama
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa Salamandra. With swimming pool, next to the swamp
Privileged environment, surrounded by pine forests next to the swamp, located between three of the most representative cities of Spain: Toledo, Ávila and Madrid. Very interesting design house in the shape of an A, with a lot of light, in the middle of nature, with views of the lake and mountains. Private garden of 1500 m2 with private pool. Furnished terrace with BBQ. 7 km from San Martín de Valdeiglesias (where all kinds of services are available). Possibility of carrying out a variety of aquatic activities.

Nature in the San Juan swamp
In the middle of nature, surrounded by pine trees and 200 meters from the Bungalows beach. First floor: living room with terrace with wonderful views of the pine forest and the surroundings of the swamp. Double bedroom, bedroom with two beds, bathroom and kitchen. Ground floor: large multifunctional living room with bar, ping pong, billiards, dartboard and an apartment with two beds. A place that invites you to relax with the possibility of doing nautical and multi-adventure activities in the swamp area.

Cabaña del Burguillo
Idyllic environment surrounded by wild nature, located in a pinewood on the edge of the lake with direct access to the beach. Ideal for couples, the house consists of a spacious living room, fully equipped kitchen, bedroom with double bed and extra bed or optional cradle, bathroom and large terrace overlooking the lake. Place that invites you to rest, with the possibility of carrying out nautical and sports activities. Pets are allowed, except february, march & april due to pine processionary.

Virgen de Gracia Viewpoint
A unique house restored in 2023, dating back to the 16th century, built on 10th century ruins. It is located in the Jewish quarter, next to the Virgen de Gracia viewpoint, on a pedestrian street where silence and tranquility prevail. This small house stands out above all for the care with which it has been restored, trying as much as possible to preserve its oldest essence. The added details give it that peculiar touch, which together with its special architecture make it very special.

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.

The Rascafria granary
Escape the daily grind at this unique property in the Sierra de Guadarrama, IG @elpajarderascafria. Located in the beautiful village of Rascafría, the starting point for the best routes to Peñalara. Ideal for a family holiday at any time of the year. We also organise retreats (IG @nkalmaretreats) for groups or celebrations, featuring a range of workshops. The pool has a massage bench in summer. In winter you can enjoy the fireplace. One hour from Madrid and Segovia.

Spectacular views one hour from Madrid
Disconnect and enjoy a paradise just an hour from Madrid. Spectacular views, infinity pool, fireplace, garden with barbecue, walking access to the lake and everything you need to enjoy with your family or friends. No parties. No smoking. Pets are not allowed. Late check-out ONLY WITH PRIOR NOTICE: ask for price Tourist licence: CRU05005000026499 According to decree 933 we will request the details of the guests according to these regulations.

Casa Josephine Riofrío - retreat 1 hour from Madrid
Casa Josephine Riofrío B&B is a capsule of peace and rest one hour from Madrid, in a quiet village in a protected landscape at the foot of the mountain. A place where time passes differently. A retreat, a space to create, rest, or work at a different pace. A house completely renovated in 2022 with an architectural and interior design project based on geometry, materials and proportions, signed by Casa Josephine Studio. License VUT 40/718

House with a garden and pool in Navacerrada
A detached house where you can enjoy a quiet stay, with a beautiful garden and private seasonal pool, and in a unique environment. Ideal for relaxing, as a starting point for mountain routes or enjoying summer or winter in the mountains. A 7-minute walk to the town center and 7 minutes to the Navacerrada reservoir. An option for families with children, couples, or small groups looking for a little nature and relaxation.

Rural Boutique with Jacuzzi and Garden
Welcome to the Pertenera house. Immerse yourself in the luxury of our stone-surrounded Jacuzzi for two, where elegance and good taste are present in every detail of this charming house. From the comfortable bed, you can gaze at the stars through the window on clear nights. Relax in our charming courtyard with a cactus garden. Your perfect getaway less than an hour from Madrid, where style meets rural!

Cigarral de la Encarnación (The Incarnation Cigarral)
Un Cigarral, with stunning views of Toledo, a 20-minute walk from the historic center, and a five-minute drive, with an 11,000-meter garden and a magnificent swimming pool. A family of caretakers who live in a separate house across the garden take care of the property and can help you in any situation. Parking for 5 cars. Five double bedrooms, each with its own bathroom.

Romantic Triplex with Jacuzzi + Musical Thread
Discover Casa Capricho, a space designed for enjoyment ✨ The centrepiece is the private hot tub in the master bedroom, available all year round, accompanied by piped music throughout the house 🎶 Located less than an hour from Madrid, it is ideal for getaways as a couple, with friends or as a family. Relax, switch off, and create the perfect atmosphere at any time 💫
Popular amenities for house rentals in Sierra de Guadarrama
House rentals with a pool

Casa Pantano San Juan

The Pumpkin House, special for mountaineers

A little house in the countryside within the city

El Espinar: BBQ and winter Jacuzzi

House in the countryside to disconnect in Madrid. Animals

Luxury villa in the Sierra de Madrid with no steps

House next to the Pantano de Burguillo

Beautiful house in Madrid, private pool and garage
Weekly house rentals

VUT La Casa de la Vega

Casitas del Molino Grande del Duratón (Small Houses)

House in Soto del Real

Cozy and romantic little house in the mountains

Disconnect in the mountains. House with terrace & BBQ.

A cozy house that offers total privacy

Beautiful house on the side of the mountain in Segovia

El Refugio de Pedraza 1st Floor
Private house rentals

Wooden house surrounded by nature

Rural charm and comfort near Segovia and Madrid

La Villa de Pi

Charming house 1 hour from Madrid

Views of Miraflores

Finca El Rivero

F1 Madrid 2026 · VIP villa 1 minute from the circuit

Ángel's Balcony
Destinations to explore
- Metropolitano Stadium
- Santiago Bernabéu Stadium
- Chueca
- Parque Warner Madrid
- El Retiro Park
- Plaza Mayor
- La Latina
- Feria de Madrid
- Las Ventas Bullring
- Museo Nacional del Prado
- WiZink Center
- Royal Palace of Madrid
- Palacio Vistalegre
- Teatro Lope de Vega
- Aqueduct of Segovia
- Faunia
- Parque de Atracciones de Madrid
- Teatro Real
- Matadero Madrid
- Mercado De San Miguel
- Complutense University of Madrid
- Ruta de los Pueblos Negros
- Caja Mágica
- La Pinilla ski resort





