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

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83 Vacation rentals

(17) Excellent 

24

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 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 $111 / night

$684 / week

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avg. 2 hours 9 minutes

from $111 / night

19

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 $216 / night

$1,512 / week

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avg. 3 hours 39 minutes

from $216 / 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 $326 / night

$1,953 / week

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avg. 3 hours 50 minutes

from $326 / night

(1) Excellent 

18

Alpedrete Vacation chalet rental

Community of Madrid / Alpedrete

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • 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 $131 / night

$781 - $976 / week

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from $131 / 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 $52 / night

$365 / week

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avg. 2 hours 32 minutes

from $52 / night

18

Robledo de Chavela Vacation studio rental

Community of Madrid / Robledo de Chavela

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • 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 $110 / night

$704 / week

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avg. 3 hours 12 minutes

from $110 / 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

(1) Very Good 

21

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 $93 / night

$499 - $581 / week

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avg. 3 hours 12 minutes

from $93 / 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 $201 / night

$1,113 - $1,220 / week

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avg. 1 hour 55 minutes

from $201 / night

21

Cercedilla ski apartment to rent.

Community of Madrid / Cercedilla

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
This apartment, located in Cercedilla, is ideal for 5 vacationers. It offers a bedroom. 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. The kitchen is well-equipped for co …see more

from $98 / night

$684 / week

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avg. 3 hours 12 minutes

from $98 / night

35

Vacation villa rental

Community of Madrid / Hoyo de Manzanares

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This villa, located in Hoyo de Manzanares, is ideal for 12 vacationers. It offers 6 bedrooms, a private pool, an enclosed garden 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 …see more

from $462 / night

$2,690 / week

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avg. 3 hours 12 minutes

from $462 / night

(8) Very Good 

13

Vacation apartment in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 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 $62 / night

$307 / week

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avg. 2 hours 7 minutes

from $62 / night

31

Vacation chalet with swimming pool in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The villa has two floors and a large garden. On the ground floor we 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. The up …see more

from $284 / night

$1,987 / week

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from $284 / night

(1) Excellent 

15

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 $111 / night

$614 / week

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avg. 34 minutes

from $111 / night

(1) Excellent 

42

Home rental in Valdemorillo

Community of Madrid / Valdemorillo

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
House on one floor with spectacular natural park views. If you're looking to enjoy your family, friends, trips into the countryside, this villa with colonial decor immerses you in calm, relaxation and peace with nature. The space is unique for its views and tranquility. …see more

from $369 / night

$1,412 / week

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from $369 / 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 $92 / night

$645 / week

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from $92 / night

(9) Excellent 

15

Vacation apartment in Cercedilla

Community of Madrid / Cercedilla

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • 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 - $574 / week

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avg. 1 hour 48 minutes

from $68 / night

45

Vacation condo in Colmenar Viejo

Community of Madrid / Colmenar Viejo

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min
105 m2 apartment with 4 bedrooms and kitchen common room. One of them has 3 beds another 2 singles and the third with double bed. It has 2 bathrooms. Equipped with high-speed WiFi and TV. You will receive your own set of keys for free access at any time. The kitchen onl …see more

from $113 / night

$790 / week

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avg. 2 hours 40 minutes

from $113 / night

(1) Excellent 

29

Vacation chalet in Colmenar Viejo

Community of Madrid / Colmenar Viejo

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Ask about children
  • Ask about pets
We offer you live a few days with the Prairies where riding Clint Eastwod and Kirk Douglas fought the Romans in the natural settings of films like; “Spartacus”, “El Cid”, “The Good, the Bad. and the Ugly”, “For a Few Dollars More”…and more than 200 movies filmed in th …see more

from $209 / night

$1,302 / week

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avg. 1 hour 58 minutes

from $209 / night

15

Vacation b&b rental

Community of Madrid / San Lorenzo de El Escorial

50 2 1 night min

  • 50 bedrooms
  • sleeps 2
  • 1 night min
  • Car not necessary
Historic building with spacious, 8 meeting rooms (open, high ceilings and natural light), area of terraces for lunch, and Chapel. Located opposite the Royal Monastery of San Lorenzo of el Escorial, choir and cross of the fallen. Located in the Valle de los Caídos (nati …see more

from $86 / night

$602 / week

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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 $117 / night

$815 / week

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avg. 3 hours 39 minutes

from $117 / night

(1) Very Good 

53

Vacation finca with swimming pool in Valdemorillo

Community of Madrid / Valdemorillo

4 18 2 nights min

  • 4 bedrooms
  • sleeps 18
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Finca of 3 hectares with luxury house and main natural pool and capacity for 12 people. and a wooden guest house with three bedrooms and capacity for 6 people. Located in a protected park in the Sierra de Madrid, with beautiful views of the mountains and direct access t …see more

from $553 / night

$2,456 / week

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avg. 3 hours 29 minutes

from $553 / night

(19) Excellent 

9

Collado Mediano ski condo to rent.

Community of Madrid / Collado Mediano

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 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 $64 / night

$380 - $560 / week

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from $64 / 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

25

Vacation private room in Colmenar Viejo

Community of Madrid / Colmenar Viejo

1 1 2 nights min

  • 1 bedroom
  • sleeps 1
  • 2 nights min
Comfortable very spacious and bright room with 1 single bed. The apartment is not inhabited and bathroom is shared with 2 other rooms. The room has a desk with study lamp, high-speed WiFi, TV and lock. You will receive your own set of keys for free access at any time. T …see more

from $28 / night

$167 / week

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avg. 2 hours 40 minutes

from $28 / 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

50

Cercedilla ski finca to rent.

Community of Madrid / Cercedilla

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Finca 4000 m2, divided into two separate houses with a pool between them. It is located in the town of Cercedilla, with direct access to the ski resorts of Navacerrada, Cotos and Valdesqui, located in the Guadarrama National Park funicular. The first house has three bed …see more

from $506 / night

$2,731 / week

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from $506 / 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

$430 / week

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from $74 / 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 $307 / night

$1,842 / week

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avg. 3 hours 15 minutes

from $307 / night

15

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • 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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from $86 / night

12

Ski chalet to rent in Alpedrete

Community of Madrid / Alpedrete

5 2 2 nights min

  • 5 bedrooms
  • sleeps 2
  • 2 nights min
  • Ski
RENTAL 2 ROOMS IN VILLA. PRICES ARE OFFERED BREAKFAST. DEPENDING ON THE NUMBER OF ROOMS REQUIRED WILL CHANGE THE PRICE. Located one kilometer ALPEDRETE VILLAGE AND YET kilometer from the town of Collado Villalba. THE DETACHED HOUSE CONSISTS OF 2 ROOMS WITH A LARGE LIVIN …see more

from $50 / night

$258 - $430 / week

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from $50 / night

29

Private room rental in Colmenar Viejo

Community of Madrid / Colmenar Viejo

2 2 1 night min

  • 2 bedrooms
  • sleeps 2
  • 1 night min
Spacious room with bed and bathroom included matrimio suite overlooking the Plaza de Los Arcos. The apartment is not inhabited, there are 3 other rooms in the. The room has high speed WiFi, TV and lock. You will receive your own set of keys for free access at any time. …see more

from $59 / night

$375 / week

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avg. 2 hours 40 minutes

from $59 / night

(19) Excellent 

27

Vacation home with golf nearby in Robledo de Chavela

Community of Madrid / Robledo de Chavela

6 20 2 nights min

  • 6 bedrooms
  • sleeps 20
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Spectacular villa with unique charm and in an environment of great beauty. The house is situated on top of a hill, in a quiet area called the Spanish Switzerland, overlooking beautiful mountains and bucolic valleys under which the singular village of Robledo de Chavela …see more

from $513 / night

$3,591 / week

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from $513 / night

29

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
El apartamento Madera tiene 175m2 y está enclavado en la planta alta de uno de los edificios que pertenecen a la finca de Roqueo de Chavela. Está distribuido de la siguiente forma: consta de 2 dormitorios dobles, 1 dormitorio con litera, 1 dormitorio individual y un a …see more

from $197 / night

$1,375 / week

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from $197 / night

4

Valdemorillo Vacation home accommodation

Community of Madrid / Valdemorillo

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Detached house loft 38 km from Madrid and 13 Km of San Lorenzo del Escorial. Two plants. First floor with large living room and TV area with built-in living room, bedroom and bathroom. Second floor with 3 bedrooms and two bathrooms. separate pool. Terrace of 38 m2 barbe …see more

from $276 / night

$1,930 / week

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from $276 / night

(11) Very Good 

Certificate of Excellence

29

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
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

$491 - $577 / week

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Responds fast!
avg. 1 hour 33 minutes

from $73 / night

18

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 7 6 nights min

  • 3 bedrooms
  • sleeps 7
  • 6 nights min
  • Child friendly
Rural apartment in Cercedilla. 50 m away of the Cercanías Station. Next to urban bus stop and Madrid. Full kitchen. Washing machine and dishwasher, induction, bedding and complete crockery. Double bed and 5 bunk beds. Two bathrooms. Completely renovated. Exterior. Heati …see more

from $111 / night

$613 / week

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from $111 / 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

$399 - $606 / week

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from $68 / 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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avg. 2 hours 16 minutes

from $215 / night

(5) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $72 / night

$424 / week

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Responds fast!
avg. 3 hours 23 minutes

from $72 / night

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