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

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78 Vacation rentals

18

Vacation finca with indoor pool in Valdemorillo

Community of Madrid / Valdemorillo

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The house is built in Mediterranean / rustic style on several levels and has a total of about 250 square meters of living space. The house is ideal for families with children, has its own games room, large pool is heated with solar energy. The land area is 2.5 hectares …see more

from $173 / night

$1151 / week

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Responds fast!
avg. 58 minutes

from $173 / night

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 $173 / night

$1036 / week

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from $173 / 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 $98 / night

$604 / week

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Responds fast!
avg. 3 hours 43 minutes

from $98 / 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 $288 / night

$1726 / week

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from $288 / 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 $76 / night

$479 / week

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Responds fast!
avg. 3 hours 16 minutes

from $76 / 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 $346 / night

$1726 - $2186 / week

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from $346 / 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; keys will be given to guests for the room. 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, ph …see more

from $108 / night

$748 - $1183 / week

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Responds fast!
avg. 3 hours 40 minutes

from $108 / 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

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 $47 / night

$323 / week

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from $47 / night

8

Vacation apartment with shared pool in Moralzarzal

Community of Madrid / Moralzarzal

3 6 90 nights min

  • 3 bedrooms
  • Sleeps 6
  • 90 nights min
  • Swimming pool
  • Child friendly
It is a third floor facing the pasture with two terraces (overlooking the Maliciosa and the other to the pasture). Urbanization is the best of the mountain, has 3 tennis courts, a football / basketball court, playground and extensive gardens. It has covered garage and s …see more

from $24 / night

$162 / week

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from $24 / 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 $59 / night

$349 / week

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from $59 / 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 $57 / night

$398 / week

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from $57 / night

36

Vacation villa with swimming pool in Guadarrama

Community of Madrid / Guadarrama

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 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. ONE NIGHT PRICES FOR 1 (Saturday-Sunday): 45 € / night per person and minimum 8 people. For stays of only 1 night, …see more

from $242 / night

$944 - $2273 / week

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Responds fast!
avg. 3 hours 48 minutes

from $242 / 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 $70 / night

$484 - $1289 / week

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from $70 / 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 $254 / night

$1266 / week

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from $254 / night

(1) Very Good 

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 $403 / night

$2301 / week

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from $403 / night

20

Vacation chalet in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Pet friendly
The villa has two floors and a large garden. On the ground floor we can find the living room with a cozy fireplace and a large table. The kitchen is completely equipped. In addition, on this floor there is a bathroom and a cozy conservatory overlooking the mountains. Th …see more

from $231 / night

$1611 / week

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from $231 / night

(1) Excellent 

21

Vacation home in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Building Gravelines. Urbanización with large green areas. Views of the garden and the monastery. Great social and sports area with restaurant, pool, gym, tennis court, paddle tennis courts, playgrounds, etc. Bus to Madrid at the entrance station. Close to shopping area …see more

from $70 / night

$403 / week

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from $70 / night

(5) Excellent 

32

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 $130 / night

$904 / week

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from $130 / night

(5) Excellent 

25

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 $81 / night

$564 / week

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Responds fast!
avg. 2 hours 7 minutes

from $81 / 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 $53 / night

$319 - $371 / week

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from $53 / night

10

Vacation private room rental

Community of Madrid / Alpedrete

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
RENTAL ROOM IN VILLA IN PRIVATE URBANIZATION, QUIET AND EASY PARKING. THE PRICE IS PER ROOM FURNISHED WITH DOUBLE BED AND LARGE CLOSET. Area ideal for cycling and hiking. TYPICAL wide range of restaurants in the area. Located one kilometer Collado Villalba and Alpedrete …see more

from $47 / night

$231 / week

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from $47 / night

(5) Very Good 

22

Puerto de Navacerrada ski condo to rent.

Community of Madrid / Puerto de Navacerrada

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ski
  • Child friendly
  • Ask about pets
holiday apartment in la sierra, perfect condition in the best area of the puerto de navacerrada, officially recognized as National Park, perfect for lovers of snow, and nature for families or athletes, fully furnished, has garage included in the price, very quiet and wi …see more

from $52 / night

$323 - $564 / week

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Responds fast!
avg. 1 hour 19 minutes

from $52 / night

(9) Very Good 

25

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 $65 / night

$414 - $495 / week

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Responds fast!
avg. 1 hour 57 minutes

from $65 / night

(17) 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 $60 / night

$356 - $525 / week

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from $60 / night

15

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • 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 $87 / night

$609 / week

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from $87 / 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
  • Car not necessary
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 $93 / night

$576 - $2025 / week

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Responds fast!
avg. 1 hour 51 minutes

from $93 / night

(1) Very Good 

11

Vacation chalet with swimming pool in El Escorial

Community of Madrid / El Escorial

6 14 2 nights min

  • 6 bedrooms
  • Sleeps 14
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
The chalet is located on a plot of 3,000 meters. with pool at the foot of the Sierra de Madrid where you can enjoy a holiday, a weekend with friends or family in a quiet environment. Near the marsh Valmayor, hiking trails, cultural and gastronomic nearby villages such a …see more

from $369 / night

$1726 - $2071 / week

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Responds fast!
avg. 2 hours 41 minutes

from $369 / 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 $41 / night

$225 - $570 / week

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from $41 / night

34

Home rental in Collado Villalba

Community of Madrid / Collado Villalba

5 9 1 night min

  • 5 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
Wonderful villa in the best area of ​​the Sierra de Madrid. Located in one of the most prestigious developments in Collado Villalba, surrounded by nature and indescribable enclave. Nature and Rest 20 minutes from Madrid. More than 5,000 meters of land in the open air, …see more

from $553 / night

$3866 / week

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from $553 / night

(2) 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 $173 / night

$1036 / week

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from $173 / night

38

Home rental in Robledo de Chavela with shared pool

Community of Madrid / Robledo de Chavela

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
We María Inés and Pedro Dubié and hope that you feel comfortable in our house. Deo Gratias and House of familias.Fue our home and now is home to those looking to relax and have fun with family and friends in a different and original place. The views from the living room …see more

from $288 / night

$1381 - $1496 / week

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from $288 / night

20

Vacation home in Santa Maria de la Alameda

Community of Madrid / Santa Maria de la Alameda

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
Rural House of 240 m at two plants located in Navalespino. The ground floor has a separate bar, a dining room accommodating up to 20 people, living room with fireplace, 2 toilets and a kitchen of 22 m. equipped with iron, furnace and industrial stove, microwave, dishwas …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

24

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Gite with panoramic village of Robledo de Chavela and mountains. We have private garden and chill out with outdoor spa conservatory exclusive use. As water is heated it can be used both summer and winter. What you'll find in the house: a living room with TV, a kitchen w …see more

from $145 / night

$603 / week

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from $145 / night

26

Vacation home rental

Community of Madrid / El Escorial

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $173 / night

$1036 - $1600 / week

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from $173 / night

17

Vacation home in Becerril de la Sierra

Community of Madrid / Becerril de la Sierra

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Private garden
House garden plot of 3000 meters with over 100 ornamental trees and fruit, garden, dog house, chicken coop, heated pool with solar energy and gas-oil 10x5 dimensions. social club with tennis courts and swimming pool Located in a privileged unentorno on the southern slop …see more

from $116 / night

$812 / week

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Responds fast!
avg. 1 hour 6 minutes

from $116 / 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 $110 / night

$967 / week

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Responds fast!
avg. 2 hours 52 minutes

from $110 / 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 $53 / night

$290 / week

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Responds fast!
avg. 2 hours 54 minutes

from $53 / 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 $141 / night

$687 - $824 / week

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from $141 / night

8

Apartment rental in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
This is a loft, penthouse with beautiful views of the monastery of San Lorenzo and mountains. Being an attic, has however entrance at street level as it is a built on the slope of Mount Abantos building. The loft has separate sections for space and furniture for the bed …see more

from $70 / night

$487 / week

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from $70 / night