
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.

Retiro Park Industrial House
Bright, south-facing home in a quiet central neighborhood, just 600 meters from Retiro Park. Fun and original, with an industrial-chic vibe, this 160 m² house has lots of natural light, a small garden, and a private parking spot. Downstairs there’s a large open-plan kitchen, dining, and living area (about 70 m² / 750 sq ft), with underfloor heating and AC in every room. The kitchen is fully equipped, and we provide bed linens, towels, and all the basics you’ll need for a comfortable stay. You’ll also find a small private gym on this floor. Upstairs are the three bedrooms: • The main bedroom has a 180 x 200 cm / 71 x 79 inches bed (King Size) and a private bathroom. • The second bedroom also has a 180 x 200 cm / 71 x 79 inches bed (King Size) and shares a bathroom with the third room. • The third bedroom, which is the smallest, has a trundle bed (90 x 200 cm). It can be pulled out to create two single beds (90 x 200 cm each), placed very close together—ideal for two kids or two people who are comfortable sharing close space. There’s also the option to join them and form a 180 x 200 cm bed (King Size), suitable for a couple.
LocationValueNearby
4.99 out of 5 average rating, 143 reviews
Casa Salamandra. With swimming pool, next to the swamp
A privileged environment, surrounded by pine trees next to a marsh, located between three of the most representative cities in Spain: Toledo, Avila and Madrid. Very interesting design house in the shape of an A, with lots 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.
FamilyLocationAccuracy
4.92 out of 5 average rating, 122 reviews
The Rascafria granary
Get away from the daily grind at this unique accommodation in the Sierra de Guadarrama, IG @elpajarderascafria. Located in the beautiful town of Rascafría, the starting point for the best routes to Peñalara. Ideal for relaxing with the family at all times of the year. We also host retreats (IG @nkalmaretreats) for groups or celebrations, featuring a variety of workshops. The pool has a massage bench in summer. In winter you can enjoy the fireplace. One hour from Madrid and Segovia.
LocationFamilyKitchen
4.97 out of 5 average rating, 31 reviews
Romantic triplex with a private jacuzzi and terrace
Discover Casa Capricho, a place designed for enjoyment ✨ ✅ The house is intact and the area is functioning normally: roads and accesses are open, the reservoir and restaurants are operational. The star feature is the private jacuzzi in the master bedroom, available year-round, along with piped music throughout the house 🎶 Less than an hour from Madrid, it's ideal for getaways as a couple, with friends, or as a family. Relax, unwind, and create the perfect atmosphere at all times 💫
LocationValueNearby
4.88 out of 5 average rating, 173 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.
FamilyLocationHot tub
4.94 out of 5 average rating, 140 reviews
Lovely place with a pool in summer
Beautiful home, registered in Registry E. T. ref. no. VT-14878, two bedrooms (one double), two bathrooms, full kitchen. Separate entrance. It is the ground floor of a two-story villa (the owners live on the upper floor). Pets are allowed (max 2 medium) at an additional cost of €5 per day/pet. Independent access to the garden. Residential area. Downtown Los Molinos with all amenities a 7-minute walk away, two buses and commuter train connect with Madrid
ValueFamilyPool
4.85 out of 5 average rating, 73 reviews
House in Soto del Real
Keep it simple at this peaceful and centrally-located place. Spectacular house fully equipped with underfloor heating (cold and heat) by aerothermal. Divided into two floors, the main floor consists of an open kitchen, a full bathroom and a living-dining room. The first floor has a double bedroom and another with a trundle bed and a full bathroom (with a whirlpool bathtub) and a balcony overlooking the mountain. 60 m plot with artificial grass.
LocationFamilyCheckout
4.86 out of 5 average rating, 113 reviews
Apartamento Ocejón I mean Parents
Places of interest: Valverde de los Arroyos, Tamajón, Incredible views, Hayedo Tejera Negra. Lush oak forests, Pico Ocejón, Las Chorreras Despeñalagua, the route of the Black Villages, light, the comfort of the bed, the cozy space. You'll love my place because it's newly opened, all designed to be very comfortable, incredible views and very individual. Ideal for couples getaways. My accommodation is good for couples, adventurers, and pets.
ValueLocationHeating
4.89 out of 5 average rating, 211 reviews
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
FamilyValueCondition
5.0 out of 5 average rating, 22 reviews
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.
LocationFamilyView
5.0 out of 5 average rating, 44 reviews
Rural Boutique with Jacuzzi and Garden
Welcome to Pertenera. A boutique house less than an hour from Madrid, where rural charm meets design. The private Jacuzzi, built in next to a stone wall, is the heart of the house. The room opens onto the patio through a large glass door, and the small cactus garden invites you to have breakfast outside, read, or simply relax. A house where you can close the door and forget about everything for a while.
ValueFamilyHospitality
4.95 out of 5 average rating, 165 reviews
A little house in the countryside within the city
A beautiful country house in the city of Ávila. Ideal, cozy house with careful details designed for you to enjoy an independent stay in the middle of nature and at the same time discover the walled city. Feel at home and disconnect in the countryside, or enjoy just a 10-minute walk from the World Heritage City.
FamilyLocationParks
4.95 out of 5 average rating, 114 reviewsPopular amenities for Sierra de Guadarrama house rentals
House rentals with a pool

Dream House in Aranjuez, Madrid
ValueLocationNearby
4.91 out of 5 average rating, 228 reviews
Spectacular views one hour from Madrid
FamilyValueAccess
4.85 out of 5 average rating, 87 reviews
House next to the Pantano de Burguillo
FamilyLocationDecor
5.0 out of 5 average rating, 43 reviews
The Pumpkin House, special for mountaineers
LocationValueCleanliness
4.94 out of 5 average rating, 66 reviews
Sierra Madrid · Navacerrada · Reservoir · 8 people
LocationFamilyPool
4.86 out of 5 average rating, 29 reviews
Your home in La Pedriza
FamilyLocationCleanliness
4.91 out of 5 average rating, 34 reviews
Charming house in the heart of nature
LocationFamilyWalkability
4.94 out of 5 average rating, 86 reviews
La Serradilla, a house for tourist use in Labajos
FamilyLocationCheck-in
4.93 out of 5 average rating, 28 reviewsWeekly house rentals

Charming house at La Granja, Segovia
LocationValueBathroom
4.96 out of 5 average rating, 83 reviews
Cabaña del Burguillo
ValueLocationCheckout
4.98 out of 5 average rating, 48 reviews
Disconnect in the mountains. House with terrace & BBQ.
LocationValueWalkability
4.72 out of 5 average rating, 238 reviews
Villa in the Sierra de Madrid
LocationFamilySleep quality
4.95 out of 5 average rating, 63 reviews
Spectacular view in the Fuenfria
ValueLocationLaundry
4.83 out of 5 average rating, 192 reviews
Refugio 1900
FamilyLocationTV
5.0 out of 5 average rating, 34 reviews
Stone mountain house with pool
FamilyValueSleep quality
4.96 out of 5 average rating, 54 reviews
El Refugio de Pedraza 1st Floor
LocationValueSleep quality
4.92 out of 5 average rating, 12 reviewsPrivate house rentals

Country house with views near Madrid
FamilyLocationHospitality
4.79 out of 5 average rating, 62 reviews
the little blue house
LocationFamilyDecor
5.0 out of 5 average rating, 22 reviews
House in Pedraza
FamilyLocationCondition
4.99 out of 5 average rating, 84 reviews
Casa del Acebo
LocationFamilyKitchen
4.91 out of 5 average rating, 23 reviews
Casa La Huertona in Castroserna
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 7 reviews
La Lumbre: Charm with a year-round pool
FamilyLocationHeating
4.91 out of 5 average rating, 34 reviews
Family home for hiking trails
LocationValueAccuracy
4.98 out of 5 average rating, 53 reviews
The river house
FamilyLocationSleep quality
4.73 out of 5 average rating, 11 reviewsDestinations to explore
- Santiago Bernabéu Stadium
- Parque Warner Madrid
- Chueca
- El Retiro Park
- Metropolitano Stadium
- La Latina
- Plaza Mayor
- Feria de Madrid
- Las Ventas Bullring
- WiZink Center
- Royal Palace of Madrid
- Teatro Lope de Vega
- Faunia
- Complutense University of Madrid
- Aqueduct of Segovia
- Parque de Atracciones de Madrid
- Teatro Real
- Matadero Madrid
- Madrid Río
- Mercado De San Miguel
- Puerta de Toledo
- Parque Europa
- Círculo de Bellas Artes
- Caja Mágica





