50 Best Vacation Rentals in Sierra de Guadarrama - Holiday Lettings - Cabins

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78 Vacation rentals

18

Alpedrete Vacation chalet rental

Community of Madrid / Alpedrete

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Car not necessary
THE PROPERTY IS LOCATED 40 KMS FROM MADRID (25 MINUTES DRIVING) IN THE MOUNTAIN AREA. THE HOUSE IS A 3000 M2 PARCEL WITH TENNIS COURT AND SWIMMING POOL. HAS THREE LEVELS PERFECTLY COMUNICATED: GROUNDWITH THE KITCHEN AND BATHROOM, SECOND 80M2 SALON, THIRD ROOMS AND TWO B …see more

from $169 / night

$1009 / week

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from $169 / night

(16) Excellent 

24

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
Situated five minutes walk from the town centre, the fully furnished flat is in an ideal location for restaurants, bars, shops and local amenities. The flat is on the top floor of a four storey building with views of the mountain sierra. There is parking outside the bui …see more

from $96 / night

$589 / week

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from $96 / night

21

Vacation apartment with shared pool in Collado Villalba

Community of Madrid / Collado Villalba

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This apartment, located in Collado Villalba, is ideal for 5 vacationers. It offers 3 bedrooms, a pool access and a furnished balcony. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book or take advantage …see more

from $74 / night

$467 / week

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from $74 / night

(4) Excellent 

12

Vacation cottage in Valdemorillo

Community of Madrid / Valdemorillo

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
First of all, we want to show you a video from the cottage that was recorded some months ago (go to vimeo and look for "casa nacho y pino") 1500 square meter garden with a private swimming pool, nice trees, barbecue, canoe, a cozy porch at a private urbanization with 2 …see more

from $281 / night

$1682 / week

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from $281 / night

(1) Very Good 

14

Las Dehesas Vacation villa rental

Community of Madrid / Las Dehesas

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
The Villa Rosalva is a apartment-complex with a warm and familial atmosphere. We are perfectly situated in Las Dehesas with a spectacular view on the mountains and the Teide, the city of Puerto and the Atlantic Ocean. Within walking-distance you can reach the beach, the …see more

Pricing unknown

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Pricing unknown

30

Villa rental in Valdemorillo with swimming pool

Community of Madrid / Valdemorillo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning large luxurious villa with private pool recently renovated inside out! Located on the north west of Madrid; it's the perfect holiday home for those looking for a relax and private surrounding with fantastic views to the mountains. The beautiful Va …see more

from $260 / night

$1820 / week

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from $260 / night

51

Guadarrama Vacation home rental

Community of Madrid / Guadarrama

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Large 230sq m house with a charming 3000 sq m garden. 4 double bedrooms (one large suite with fireplace, dresser and bath), living room with fireplace, glass enclosed dining room, kitchen (with all necessary) , woodshed, independent guest house with large fireplace, m …see more

from $337 / night

$1682 - $2130 / week

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from $337 / night

14

Vacation home in Collado Villalba

Community of Madrid / Collado Villalba

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Rooms to rent in Madrid a Bus and train ride from the central; the house is in a really good location for tourists. Especially if you want to get away to relax. We also have numerous bars, restaurant, markets, supermarket, pharmacy, shop of all kinds. Perfect for visi …see more

from $68 / night

$410 / week

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from $68 / night

4

Vacation private room in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
Our place is close to the historic part of town, several restaurants and dining options, and has great views of the mountains. You’ll love our home because of the location, easy access to both the historic centre and the surrounding natural space. Our place is good for …see more

from $45 / night

$314 / week

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from $45 / night

(2) Very Good 

22

Vacation villa in Los Molinos

Community of Madrid / Los Molinos

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Detached villa in the Sierra de Madrid with a view to the mountain in the town of Los Molinos, 1 km. From the center of the village, 3 floors, 4 bathrooms, 4 bedrooms, garage and terrace - garden with barbecue, room games, billiard, darts, etc. Computer, free Wi-Fi. Swi …see more

from $247 / night

$1233 / week

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from $247 / night

(5) Very Good 

11

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
Stone house built in 1925, completely renovated, retains some of the original, convenient and comfortable to spend a few days in the Sierra, family room furniture. Features: It has 3 double rooms outside, two bathrooms with shower, living room with sofa bed and TV, kitc …see more

from $68 / night

$471 - $1256 / week

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from $68 / night

(5) Excellent 

12

Vacation apartment in Cercedilla

Community of Madrid / Cercedilla

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
It is located in the heart of the village of Cercedilla, in the Plaza Mayor, where you can enjoy its restaurants, bars, shops and stroll through its streets. Ideal for couples, families with children and athletes. The village environment, Las Dehesas Cercedilla Puerto d …see more

from $55 / night

$385 / week

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from $55 / night

31

Collado Mediano Vacation apartment rental

Community of Madrid / Collado Mediano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Opened in 2007, new account with innovative and modern facilities: hot water and heating during 24 hours a day, phone, Internet, complete and spacious bathrooms, apartments with plenty of natural light in all instances and ceramic floors among other details, all accompa …see more

from $136 / night

$664 - $796 / week

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from $136 / night

8

Cercedilla ski apartment to rent.

Community of Madrid / Cercedilla

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Ski
  • Child friendly
Apartamento de 1 Dormitorio con Cama de Matrimonio y dos sofas cama, de dos camas cada uno, con maravillosas vistas, salón comedor y cocina americana con barra al salón. Ultimo piso con vistas al Vallle. tiene doble ventana con doble pared para aislamiento acustico y t …see more

from $85 / night

$589 / week

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from $85 / night

(1) Very Good 

12

Vacation apartment rental

Community of Madrid / Moralzarzal

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
prime location in the city, with easy access (1-3 min. walk) to supermarkets, medical center, pharmacy, bus station, entertainment area ... Free public parking. WIFI. The apartment is located in a natural environment. Not surprisingly, the municipality is within the R …see more

from $57 / night

$337 / week

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from $57 / night

28

Vacation finca with swimming pool in Valdemorillo

Community of Madrid / Valdemorillo

4 14 2 nights min

  • 4 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
3 hectare farm with luxury and natural pool principal and up to 14 people. Also rent in the same building, wooden house can accommodate 6 people. Located in a protected park in the Sierra de Madrid, with beautiful mountain views and direct access to hiking in the countr …see more

from $393 / night

$2242 / week

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from $393 / night

(8) Very Good 

13

Vacation apartment in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Suitable for children age 5+
  • Car not necessary
  • Ask about pets
Garret rustica in the Centre of San Lorenzo de el Escorial, next to the Town Hall square and 200 metres from the monastery. Opposite the health centre and 50 meters from the municipal market. 500 m from the bus station. 664 and 661 numbers take you from Moncloa station …see more

from $51 / night

$281 / week

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from $51 / night

(5) Excellent 

9

Ski apartment to rent in Matalpino

Community of Madrid / Matalpino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Ground floor apartment located in the National Park of the Upper Basin of the Manzanares, with pool and garden shared only with the owner. A place to enjoy nature and perfect for those who want to improve their English in a very special way. The property is let to 4 peo …see more

from $127 / night

$880 / week

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from $127 / night

(4) Excellent 

18

Robledo de Chavela Vacation villa rental

Community of Madrid / Robledo de Chavela

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa has 250 square meters is located in Robledo de Chavela, mountain town with beautiful mountain walks and hiking. Possibility of horse riding. Tourist visits to the monuments of San Lorenzo de El Escorial. Walking up the Rio Cofi. The villa is an excellent start …see more

from $197 / night

$953 - $1177 / week

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from $197 / night

9

Puerto de Navacerrada ski apartment to rent.

Cercedilla / Puerto de Navacerrada

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Ski
  • Ask about children
  • Pet friendly
Es un precioso apartamento en plena montaña a 1800 M de altura en la estación de esquí en el Puerro de Navacerrada con unas vistas increíbles, ideal para amantes del esquí, senderismo, bicicleta, o simplemente para desconectar y cargar pilas, se alquila por fines de s …see more

from $40 / night

$219 - $555 / week

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from $40 / night

(1) Excellent 

28

Vacation apartment with shared pool in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Quartzite Rural House consists of: large living room with access to the covered porch with view of pool and Valley bedroom quadruple (1 double + 2 single) 1 triple bedroom (bunk + individual) 2 double bedrooms (2 beds in each) 2 bathrooms 1 toilet kitchen fully equipped …see more

from $269 / night

$1883 / week

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from $269 / night

(2) Very Good 

29

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Car not necessary
  • Private garden
Rural apartment with panoramic views to the mountains and the village of Robledo de Chavela. We have private garden and chill out with outdoor spa for exclusive use. What you will find in the House: a living room with flat tv 32 ', a kitchen equipped with electrical ap …see more

from $152 / night

$583 / week

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from $152 / night

(2) Excellent 

18

Ski condo to rent in Puerto de Navacerrada

Cercedilla / Puerto de Navacerrada

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • Min stay varies
  • Ski
  • Child friendly
Loft Puerto de Navacerrada is a new modern and sophisticated housing concept. Unique in the area and exclusive, perfect to unwind from the city or for various sports, including cycling, mountain biking, hiking, climbing, winter sports season, snowshoe routes, etc. It is …see more

from $73 / night

$510 / week

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from $73 / night

(1) Excellent 

21

Vacation home rental

Community of Madrid / Santa Maria de la Alameda

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Equipment: Fully furnished, kitchen appliances Heating. Appliances: refrigerator, microwave, electric oven, toaster, Dishwasher Audio Video: 4 television, wi-fi Outside: barbecue, outdoor furniture, tables, chairs and deck chairs, fenced private pool, porch linen: blank …see more

from $79 / night

$841 / week

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from $79 / night

(1) Excellent 

29

Valdemorillo Vacation cottage rental

Community of Madrid / Valdemorillo

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
Country wooden house farm located in a protected park in the Sierra de Madrid, with beautiful views and direct access to hiking in the countryside or bike rides. Located 14 km from El Escorial, 7km from Valdemorillo, 40 km from Madrid and 60km from the airport. The hous …see more

from $169 / night

$1009 / week

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from $169 / night

37

Vacation villa with swimming pool in Guadarrama

Community of Madrid / Guadarrama

4 13 1 night min

  • 4 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful rustic house with garden of 5,000 m2, with barbecues, private pool, swings, basketball basket, children's games and more. Children under 3 free. Pre-cleaning expenses: 30 € normal cleaning; 80 € cleaning. You tell what kind of house cleaning is desired. For st …see more

from $236 / night

$1065 - $2854 / week

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from $236 / night

26

Vacation home rental

Community of Madrid / El Escorial

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
detached house in a quiet and beautiful setting with common areas: salt pool, lighted paddle tennis, football, basketball and children play. South orientation. Very bright. Large living room with Home cinema and direct access to the terrace, kitchen with all appliances …see more

from $135 / night

$841 - $897 / week

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from $135 / night

(7) Excellent 

Certificate of Excellence

15

Vacation home with shared pool in Moralzarzal

Community of Madrid / Moralzarzal

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Guest house near Madrid in a very calm and quiet. It has 2 bedrooms, 1 bathroom, kitchen and living room with chimenea.Se you can put a sofa-bed for two person, surcharge payment. Garden of 1500 m² with pool, barbecue, playground and parking for the common use of tenant …see more

Certificate of Excellence

from $90 / night

$628 / week

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from $90 / night

(7) Very Good 

23

Apartment rental in San Lorenzo de El Escorial with shared pool

Community of Madrid / San Lorenzo de El Escorial

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Apartment ideal for couple with child in residential quiet pool of 50m and children's pool, tennis, paddle, playground, sauna, clubhouse and restaurant in Garden located at foot of Mt. abantos. …see more

from $63 / night

$404 - $482 / week

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from $63 / night

(1) Excellent 

29

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Spend some wonderful days in Cercedilla, the prettiest village in the mountains of Madrid. Three-storey villa, 150m2 home and 120 m2 private garden. Beautiful complex with pool and tennis court and parking 50 km from Madrid. Located in a complex with spectacular mountai …see more

from $107 / night

$942 / week

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from $107 / night

15

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
La Pizarra es un bungalow de 35m2 perfecto para una pareja e incluso para compartir con 1 ó 2 niños. Está compuesto por un dormitorio con cama de matrimonio, un salón-comedor con cocina americana y sofá/cama. Un cuarto de baño con bañera infantil. En su parte exterior …see more

from $90 / night

$628 / week

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from $90 / night

(16) Excellent 

9

Collado Mediano ski condo to rent.

Community of Madrid / Collado Mediano

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Ski
Warm apartment in one of the towns best connected with the rest of the Sierra de Madrid, 15 minutes from La Pedriza and the newly created National Park Guadarrama, also has direct connection with Madrid commuter and bus. The house is located near the center of town, wit …see more

from $59 / night

$347 - $512 / week

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from $59 / night

(1) Very Good 

18

Guadarrama Vacation apartment rental

Community of Madrid / Guadarrama

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Beautiful apartment of 70m 2 in Guadarrama, in the urban area. Aesthetics: modern and comfortable, spacious and bright spaces. Living room with exit to terrace, dining room, study area, bedroom with bathroom and a second bathroom, kitchen with indoor clothesline. Idea …see more

from $68 / night

$368 - $525 / week

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from $68 / night

(4) Very Good 

19

Valdemanco Vacation cottage rental

Community of Madrid / Valdemanco

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
Accommodation consisting of 2 Villa Semidetached houses with 8 seats each, are rented together or separately. Each chalet has 3 bedrooms, 3 bathrooms, rural kitchen with BBQ, very spacious living room, Garden, terrace, kitchen with all the necessary accessories. Each ch …see more

from $225 / night

$1569 / week

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from $225 / night

19

La Navata Vacation apartment rental

Community of Madrid / La Navata

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Our apartment is located on the ground floor of the chalet with views to the garden. It has two bedrooms, living room, kitchen and bathroom. You can accommodate 4 people and is located two blocks from bus stop, direct to the Centre of Madrid. The space to enjoy the tra …see more

from $78 / night

$542 / week

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from $78 / night

46

Vacation apartment in Collado Mediano

Community of Madrid / Collado Mediano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Opened in 2007, new account with innovative and modern facilities: hot water and heating during 24 hours a day, phone, Internet, complete and spacious bathrooms, apartments with plenty of natural light in all instances and ceramic floors among other details, all accompa …see more

from $72 / night

$407 - $488 / week

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from $72 / night

(1) Good 

12

Apartment rental in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
1 bd flat in very center of old town, situated in a XVIII century building, fully refurbished inside. 3rd (top) floor, no lift but easy staircase. Enjoys great views over monastery, mountains and the old square. Wide selection of restaurants, cafés and shops nearby. Qui …see more

from $62 / night

$367 - $485 / week

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from $62 / night

(1) Excellent 

22

Vacation apartment in Santa Maria de la Alameda

Community of Madrid / Santa Maria de la Alameda

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Our Apartments, built in stone and wood, have a capacity for 4 or 6 people each. In an environment of Nature The best experience of rural accommodation less than 1 hour from Madrid. An ideal place to enjoy nature, with friends, with family or friends environment. Stroll …see more

from $96 / night

$505 / week

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from $96 / night

31

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
The accommodation has everything you need to make you feel at home, is very spacious and bright. It has 3 bedrooms with 2 bathrooms. There are 4 single beds and a bed of 1.80 meters. The kitchen is completely equipped. You can also enjoy the garden which is very large a …see more

from $96 / night

$667 / week

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from $96 / night

8

Apartment rental in Collado Villalba with shared pool

Community of Madrid / Collado Villalba

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
functional and comfortable apartment complete 65 m. upstairs bedroom, bathroom with shower, living room-kitchen, courtyard garden of 25 m., garage, Wifi fiber, gated community, pool and garden. In the heart of the Sierra de Madrid, well connected by A6, cinemas, superma …see more

from $51 / night

$309 - $359 / week

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from $51 / night

1