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

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Sierra de Guadarrama

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76 Vacation rentals

(17) 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 $105 / night

$645 / week

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Responds fast!
avg. 3 hours 27 minutes

from $105 / night

18

Alpedrete Vacation chalet rental

Community of Madrid / Alpedrete

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • 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 $148 / night

$614 / week

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from $148 / 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 $309 / night

$1,853 / week

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from $309 / night

51

Guadarrama Vacation home rental

Community of Madrid / Guadarrama

5 8 3 nights min

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Large 280sq 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, ma …see more

from $369 / night

$1,843 / week

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avg. 3 hours 20 minutes

from $369 / 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 $50 / night

$344 / week

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from $50 / night

14

Vacation home in Collado Villalba

Community of Madrid / Collado Villalba

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights 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 $210 / night

$1,470 / week

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avg. 3 hours 41 minutes

from $210 / 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

12

Robledo de Chavela Vacation studio rental

Community of Madrid / Robledo de Chavela

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
This studio, located in Robledo de Chavela, is ideal for 3 vacationers. It is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book. The kitchen is well-equipped for cooking up your favorite meals. Enjoy your feast arou …see more

from $92 / night

$647 - $714 / week

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avg. 2 hours 7 minutes

from $92 / night

(1) Very Good 

22

Vacation apartment with shared pool, golf nearby 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 $84 / night

$457 - $533 / week

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avg. 2 hours 7 minutes

from $84 / night

12

Ski home to rent in Manzanares el Real

Community of Madrid / Manzanares el Real

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
This house, located in Manzanares el Real, is ideal for 8 vacationers. It offers 4 bedrooms, a furnished terrace and WiFi. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book in front of the fireplace or …see more

from $210 / night

$1,163 - $1,268 / week

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avg. 1 hour 58 minutes

from $210 / night

(1) Excellent 

15

El Escorial Vacation apartment rental

Community of Madrid / El Escorial

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
In the municipality of El Escorial, on the slopes of the Sierra de Guadarrama, I offer a detached single-family housing -including an apartment with separate entrance comprising entrance hall, two large rooms and bathroom with tub. A stay living-dining-kitchen. It has a …see more

from $68 / night

$400 - $606 / week

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avg. 3 hours 44 minutes

from $68 / 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 $56 / night

$346 - $519 / week

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avg. 1 hour 45 minutes

from $56 / night

(4) Excellent 

12

Vacation apartment rental

Community of Madrid / Moralzarzal

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $62 / night

$369 / week

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Responds fast!
avg. 3 hours 58 minutes

from $62 / night

39

Vacation apartment in Galapagar

Community of Madrid / Galapagar

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
It is a very cozy, very bright as it is south facing. Has as many services around: bus stop (Madrid, El Escorial, Colmenarejo), supermarkets, banks, post office, shops of all kinds ... Galapagar is a strategic point to visit Madrid and surrounding areas such as San Lore …see more

from $28 / night

$247 - $272 / week

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from $28 / night

(2) Excellent 

31

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • 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 $105 / night

$734 / week

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Responds fast!
avg. 1 hour 13 minutes

from $105 / 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 $105 / night

$731 / week

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from $105 / night

(6) 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 $74 / night

$516 - $1,376 / week

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from $74 / 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 $139 / night

$964 / week

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from $139 / 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 $215 / night

$1,044 - $1,351 / week

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avg. 1 hour 27 minutes

from $215 / night

15

Vacation studio in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

Studio 5 2 nights min

  • Studio
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden
It is a studio-flat with all amenities. Very quiet room to rest. perfect to enjoy the countryside and with all amenities nearby and not far from downtown situation. The comfortable and spacious beds. Come to know you'll love. Refraining guests for parties, provides acco …see more

from $62 / night

$369 - $885 / week

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avg. 1 hour 1 minutes

from $62 / night

(9) Excellent 

15

Vacation apartment in Cercedilla

Community of Madrid / Cercedilla

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
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 $68 / night

$402 / week

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Responds fast!
avg. 2 hours 49 minutes

from $68 / 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 $271 / night

$1,351 / week

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avg. 3 hours 16 minutes

from $271 / night

(19) 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 $65 / night

$382 - $563 / week

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from $65 / night

(8) Very Good 

13

Vacation apartment in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $62 / night

$307 / week

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avg. 2 hours 1 minutes

from $62 / night

(1) Excellent 

21

Vacation home in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $74 / night

$433 / week

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from $74 / night

22

Vacation apartment rental

Community of Madrid / Galapagar

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
new apartments in the Sierra de Madrid, Galapagar. Excellent area for sightseeing, hiking, eating at the best restaurants, activities, entertainment, culture, well connected. The private swimming pool, tennis court, wifi, kitchen and common areas .. Services Tennis cour …see more

from $121 / night

$613 / week

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Responds fast!
avg. 2 hours 54 minutes

from $121 / night

31

Collado Mediano Vacation apartment rental

Community of Madrid / Collado Mediano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights 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 $149 / night

$727 / week

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from $149 / night

(10) Very Good 

Certificate of Excellence

26

Apartment rental in San Lorenzo de El Escorial with shared pool

Community of Madrid / San Lorenzo de El Escorial

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ideal for couples with child in quiet residential area with 50m pool and children's pool, tennis, paddle tennis, playground, sauna, social club and restaurant in very garden located at the foot of Mount Abantos apartment. * If deemed appropriate, a deposit (150 €) will …see more

Certificate of Excellence

from $73 / night

$492 - $578 / week

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Responds fast!
avg. 35 minutes

from $73 / night

18

Vacation apartment in El Escorial

Community of Madrid / El Escorial

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
Located in one of the most famous rural areas of the Community of Madrid, El Escorial, it is perfect for relaxing few days near the bustle of the city. In the area you can find bars, restaurants, and tours of all kinds! It has wifi, trousseau toilet and kitchen. A 1 min …see more

from $74 / night

$516 / week

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Responds fast!
avg. 2 hours 0 minutes

from $74 / night

27

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 $246 / night

$1,720 / week

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from $246 / 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 $86 / night

$602 / week

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Responds fast!
avg. 3 hours 17 minutes

from $86 / night

14

Vacation home in Manzanares el Real

Community of Madrid / Manzanares el Real

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Excellent location opposite the mountain, river and Chapel of the Sacra rock. Panoramic views and unique completely open and unobstructed mountain and mundo.Privacidad ball and privacy, ideal for relaxation, meditation, relaxation. limpio.Posibilidad fresh air and varie …see more

from $105 / night

$735 / week

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from $105 / night

56

Vacation home with swimming pool in Manzanares el Real

Community of Madrid / Manzanares el Real

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
In the natural park of Pedriza, enjoy this fabulous villa, its beautiful decor, neat garden with orchard, fruit trees and beautiful salt water pool without chlorine. In a relaxing atmosphere, quiet and wonderful views .... and be amazed, unruffled by the capricious rout …see more

from $148 / night

$958 - $1,646 / week

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from $148 / 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 $50 / night

$246 - $418 / week

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from $50 / 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 $246 / night

$1,720 / week

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from $246 / night

34

Home rental in Collado Villalba

Community of Madrid / Collado Villalba

5 9 2 nights min

  • 5 bedrooms
  • Sleeps 9
  • 2 nights 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 $590 / night

$2,457 / week

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from $590 / night

37

Home rental in Robledo de Chavela with shared pool

Community of Madrid / Robledo de Chavela

5 15 2 nights min

  • 5 bedrooms
  • Sleeps 15
  • 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 $371 / night

$1,482 / week

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from $371 / night

(10) Excellent 

16

Vacation cottage in Valdemanco

Community of Madrid / Valdemanco

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
La Mimosa is a beautiful rural cottage located on a ground floor, with a large porch and barbecue. The House has 2 double bedrooms, sofa bed, fireplace in the living room and fully equipped both the kitchen and the rest of the House. To be in a ground floor is ideal f …see more

from $215 / night

$737 / week

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Responds fast!
avg. 3 hours 25 minutes

from $215 / night

5

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
It is a cozy apartment with 2 bedrooms, a study, two bathrooms, living room, kitchen and small terrace clothesline. There is also a small balcony in the living room and another in the master bedroom. It is a 10-minute walk from the town center -Extensive culture, restau …see more

from $93 / night

$649 / week

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from $93 / night

(1) Very Good 

66

Vacation home in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Las Pozas, is a house located just outside the village, in a quiet residential area, in a natural environment surrounded by mountains, 100 meters from the River Cofi, opposite the Monte de Santa Catalina, ideal for living a rural getaway with family with friends or pare …see more

from $277 / night

$1,935 / week

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from $277 / night