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

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Sierra de Guadarrama

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54 Vacation rentals

(16) Excellent 

24

Sierra de Guadarrama 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 $91 / night

$561 / week

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from $91 / 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 urb  …see more

from $267 / night

$1602 / week

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from $267 / night

(6) Excellent 

15

Community of Madrid / Moralzarzal

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $86 / night

$598 / week

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from $86 / night

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 beautif  …see more

from $252 / night

$1764 / week

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from $252 / night

(6) Very Good 

23

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

 …see more

from $59 / night

$385 - $460 / week

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from $59 / night

31

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

 …see more

from $86 / night

$598 / week

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from $86 / night

(5) Excellent 

9

Community of Madrid / Matalpino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly

 …see more

from $121 / night

$839 / week

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from $121 / night

41

Vacation chalet with swimming pool in Valdemorillo

Community of Madrid / Valdemorillo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
In this beautiful house with private pool and Jacuzzi you can enjoy and relax in the village of Valdemorillo all year long a lovely village placed in the middle of the Sierra de Guadarrama just 25 minutes by bus to Madrid, Valdemorillo is a historical village with all  …see more

from $214 / night

$1495 - $1944 / week

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from $214 / night

18

Sierra de Guadarrama 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 $161 / night

$962 / week

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from $161 / night

(14) Excellent 

9

Community of Madrid / Collado Mediano

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ski

 …see more

from $56 / night

$337 - $464 / week

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from $56 / night

(4) Very Good 

13

Community of Madrid / San Lorenzo de El Escorial

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Ask about pets

 …see more

from $49 / night

$267 / week

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from $49 / night

22

Community of Madrid / Los Molinos

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $267 / night

$1058 / week

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from $267 / night

(1) Excellent 

27

Community of Madrid / Cercedilla

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $102 / night

$711 / week

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from $102 / night

(4) Very Good 

11

Community of Madrid / Cercedilla

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from $65 / night

$449 - $1196 / week

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from $65 / night

(2)  

12

Community of Madrid / San Lorenzo de El Escorial

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Car not necessary

 …see more

from $214 / night

$267 / week

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from $214 / night

(1) Very Good 

14

Sierra de Guadarrama 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) Excellent 

21

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

 …see more

from $65 / night

$374 - $534 / week

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from $65 / night

24

Vacation apartment in Sierra de Guadarrama

Community of Madrid / San Lorenzo de El Escorial

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
Wide apartment, 3 bathrooms, 1 bathrooms, 1 bath, living room, kitchen with office and wide terraceGreat location in city center in a very peaceful zone.Shared gardenthe best area of the Sierra de MadridPerfect for familiesSan Lor  …see more

Pricing unknown

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Pricing unknown

(1)  

29

Community of Madrid / Guadarrama

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Ask about children
  • Private garden

 …see more

from $134 / night

$801 - $1399 / week

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from $134 / night

(1) Very Good 

18

Community of Madrid / Guadarrama

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $65 / night

$351 - $500 / week

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from $65 / night

(1) Good 

12

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

 …see more

from $59 / night

$350 - $462 / week

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from $59 / night

(3) Very Good 

22

Community of Madrid / Puerto de Navacerrada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ski
  • Child friendly
  • Ask about pets

 …see more

from $52 / night

$299 - $412 / week

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from $52 / night

100

Vacation villa with swimming pool in Sierra de Guadarrama

Community of Madrid / Los Abetos, Moralzarzal

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
House located in the countryside, on a hill overlooking the valley of San Miguel, in the Es Portixol. Absolute quiet, close to some of the most beautiful and wild island coves. About 7 minutes from the village of San Miguel and San Mateo, Santa Gertrudis 15 minutes, 25  …see more

from $210 / night

$1469 - $2713 / week

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from $210 / night

39

Community of Madrid / El Escorial

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $699 / night

$4892 / week

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from $699 / night

12

Community of Madrid / Alpedrete

5 4 2 nights min

  • 5 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ski
  • Ask about children
  • Ask about pets

 …see more

from $43 / night

$225 - $449 / week

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from $43 / night

(2) Excellent 

19

Community of Madrid / Hoyo de Manzanares

7 10 2 nights min

  • 7 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly

 …see more

from $454 / night

$1442 / week

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from $454 / night

25

Community of Madrid / Galapagar

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $145 / night

$1015 / week

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from $145 / night

9

Cercedilla / Puerto de Navacerrada

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Ski
  • Ask about children
  • Pet friendly

 …see more

from $49 / night

$209 - $529 / week

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from $49 / night

11

Community of Madrid / Matalpino

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ski
  • Child friendly

 …see more

from $118 / night

$695 / week

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from $118 / night

(1) Excellent 

28

Community of Madrid / Robledo de Chavela

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $264 / night

$1847 / week

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from $264 / night

(1) Excellent 

29

Community of Madrid / Colmenar Viejo

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $161 / night

$1068 / week

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from $161 / night

15

Community of Madrid / Robledo de Chavela

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $93 / night

$651 / week

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from $93 / night

37

Community of Madrid / Guadarrama

4 13 1 night min

  • 4 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $191 / night

$1331 / week

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from $191 / night

53

Community of Madrid / Colmenar Viejo

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden

 …see more

from $161 / night

$1068 / week

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from $161 / night

12

Community of Madrid / Moralzarzal

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from $54 / night

$321 / week

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from $54 / night

25

Community of Madrid / El Escorial

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $161 / night

$855 - $1004 / week

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from $161 / night

(2) Very Good 

29

Community of Madrid / Robledo de Chavela

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Car not necessary
  • Private garden

 …see more

from $145 / night

$556 / week

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from $145 / night

15

Community of Madrid / El Escorial

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $59 / night

$348 - $527 / week

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from $59 / night

22

Community of Madrid / Los Molinos

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $57 / night

$399 / week

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from $57 / night

19

Community of Madrid / La Navata

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from $74 / night

$516 / week

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from $74 / night