40 Best Vacation Rentals in Roccastrada - Holiday Lettings - Cabins

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990 Vacation rentals

(1) Excellent 

19

Roccastrada Vacation home rental

Province of Grosseto / Roccastrada

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 45 mi
  • Child friendly
Casa Dell' Artista ,situated in the medieval perched village of Roccatederighi in the heart of Tuscany, is 45 minutes drive from Siena. The house, which has its own small turret & secluded garden offers spectacular views over the Maremma Plain and to the sea beyond. Th …see more

from $110 / night

$770 / week

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from $110 / night

9

Vacation apartment in Roccastrada

Province of Grosseto / Roccastrada

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
The apartment is located close to the Centre of Roccastrada and just a short distance from the public gardens in the country. As soon as you enter there is the kitchen followed by 2 bedrooms: 1 double (with double bed) and one with 2 single beds. Bathroom and small stor …see more

from $123 / night

$860 / week

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from $123 / night

(6) Excellent 

35

Vacation townhouse rental

Province of Grosseto / Roccastrada

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
* * WE OTHER APARTMENTS AND ROOMS AVAILABLE * * SEE OTHER ADS FOR LA PESCAIA RESORT! 450 years of tradition-150 hectares of The Tolomei family charm opens his estate to guests who love nature A historic property with a long equestrian tradition-surrounded by 150 acres …see more

from $273 / night

$1,859 / week

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from $273 / night

6

Vacation b&b in Roccastrada

Province of Grosseto / Roccastrada

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 52 mi
  • Child friendly
  • Ask about pets
The farmhouse is immersed in the green hills of the Maremma between the villages of Roccastrada, Sassofortino and Montemassi. Externally has a beautiful square surrounded by olive trees from which you can admire the Maremma landscape, including our 21 acre farm in which …see more

from $93 / night

$645 / week

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from $93 / night

36

Vacation apartment with shared pool in Roccastrada

Province of Grosseto / Roccastrada

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
* * WE OTHER APARTMENTS AND ROOMS AVAILABLE * * SEE OTHER ADS FOR LA PESCAIA RESORT! 450 years of tradition-150 hectares of The Tolomei family charm opens his estate to guests who love nature A historic property with a long equestrian tradition-surrounded by 150 acres …see more

from $271 / night

$1,843 / week

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from $271 / night

16

Vacation apartment in Roccastrada

Province of Grosseto / Roccastrada

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 28 mi
  • Child friendly
The House called ULIVI has a beautiful view over the Maremma plain, in the hills cultivated with olive trees and vineyards on the road of Monteregio wine, with its beautiful Wineries: Rocca di Montemassi and Rocca di Frassinello, until you can see the islands of Giglio …see more

from $93 / night

$615 / week

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from $93 / night

4

Apartment rental in Roccastrada

Province of Grosseto / Roccastrada

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
Small apartment in the historic centre of medieval Sticciano Country composed of a bedroom, kitchen and bathroom. Place on top of a hill in the Maremma in 30 minutes from the sandy beaches of Castiglione della Pescaia and an hour from Siena and from terme di Saturnia. T …see more

from $62 / night

$430 / week

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from $62 / night

18

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
Generally known as "The Gaspero home", the structure faithfully respects the typical Tuscan houses of the late nineteenth century, with exposed beams, stone stairs and stone. Small curiosity, the name comes from the fact that in the past there lived a "character" settin …see more

from $99 / night

$516 - $602 / week

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from $99 / night

(10) Excellent 

8

Vacation farmhouse in Roccastrada

Province of Grosseto / Roccastrada

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 35 mi
  • Child friendly
  • Air conditioning
Each simple room decorated in theme and attention to detail from the chandeliers to mirrors the colors. The room of the Sun is located on the first floor, east-facing, furnished in Bambuí, he wants to recreate the environment of the marsh The room has, shower room with …see more

from $111 / night

$774 / week

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from $111 / night

23

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 mi
  • Suitable for children age 5+
  • Air conditioning
Lovely apartment 50 m2 independent, with fully equipped kitchen, bathroom, double bedroom, twin-bedded room (in passing), Garret with roof window and balcony. It is the country house of my family, we live in Firenze (100 km) and there we come often for vacation because …see more

Pricing unknown

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(1) Excellent 

4

Vacation farmhouse with shared pool in Roccastrada

Province of Grosseto / Roccastrada

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Old stone farmhouse surrounded by greenery, on two floors, is fully air-conditioned and equipped with stereo, surrounded by exclusive use of illuminated gardens and equipped; Pensione Completa e Depandace outside of the House. Ground floor: panoramic Veranda of appro …see more

Pricing unknown

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Pricing unknown

12

Farmhouse rental in Roccastrada

Province of Grosseto / Roccastrada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Pet friendly
  • Private garden
The House is located about 1.5 km from the village of Ribolla/Roccastrada (Grosseto) on a quiet hillside with stunning panoramic views of Evergreen hills of Maremma and the sea in the distance. It is accessible via a good paved road. The House is accessed through the …see more

Pricing unknown

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Pricing unknown

18

Vacation farmhouse in Roccastrada

Province of Grosseto / Roccastrada

8 30 Min stay varies

  • 8 bedrooms
  • Sleeps 30
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Hotel Residence Villa Sadhana was born in an ancient stone farmhouse of the late ' 800/' 900 beginning recently restored and returned to the original splendour by the owners and managers (Mauritius and Premnath) who wanted to strongly, with extreme tenacity and imme …see more

Pricing unknown

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13

Roccastrada Vacation home rental

Province of Grosseto / Roccastrada

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
Il Tufolino is a house in the middle of Roccatederighi. From the house you have stunning panoramic views into the Maremma Plan. We restored it carefully to a modern and comfortable standard. Only a few steps and you can enjoy your Cappuccino in one of the little bars. I …see more

from $212 / night

$1,474 / week

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from $212 / night

8

Finca rental in Roccastrada

Province of Grosseto / Roccastrada

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
Holiday House in Tuscany Roccastrada località le piscean way.. The apartment consists of: living room Kitchen Bathroom bedroom twin bedroom with two single beds Magnificent playground pool, parking 40 minutes Away from the sea, 30 minutes from grosseto to path to montan …see more

from $123 / night

$738 / week

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from $123 / night

(12) Excellent 

4

Vacation farmhouse in Roccastrada

Province of Grosseto / Roccastrada

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Air conditioning
Each simple room decorated in theme and attention to detail from the chandeliers to mirrors the colors. The room of the Marina is located on the first floor, facing north, furnished with style Bounty Marina The room has a private bathroom with shower and bedroom with a …see more

from $62 / night

$431 / week

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from $62 / night

(11) Very Good 

9

Vacation apartment in Roccastrada

Province of Grosseto / Roccastrada

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Air conditioning
All apartments are furnished in theme and attention to detail from the chandeliers to mirrors the colors. The apartment Vecchia Maremma is located on the first floor, facing south, furnished with rustic furniture, it wants to recreate the atmosphere of the old country h …see more

from $148 / night

$1,032 / week

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from $148 / night

15

Vacation apartment in Roccastrada

Province of Grosseto / Roccastrada

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Newly renovated apartment in an old (XVIII-XIX c.) stone country house nestled in the Tuscan countryside. The apartment (45 m2) on the first floor has 1 bedroom, a bathroom, a living room with a sofa bed and a kitchenette. It's fully equipped and can provide accommodati …see more

from $87 / night

$431 / week

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from $87 / night

7

Vacation farmhouse in Roccastrada

Province of Grosseto / Roccastrada

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
On the ground floor of our farmhouse of 1600, rent all year long even for short periods, a nice apartment fully furnished with internet access and can accommodate up to 4 people. Just a few metres from the medieval village of Torniella-Roccastrada (Gr) and close to the …see more

from $75 / night

$496 / week

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from $75 / night

11

Vacation apartment in Roccastrada

Province of Grosseto / Roccastrada

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
The medieval apartment is located in the historical centre of Roccastrada within walking distance of the clock tower, the Church of s. Nicola and terraces of the country from which you can admire the marvellous Maremma Valley that ends in the seaside resort of Follonica …see more

from $123 / night

$860 / week

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from $123 / night

(9) Very Good 

6

Vacation farmhouse in Roccastrada

Province of Grosseto / Roccastrada

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Air conditioning
Each of the apartments in Maremma, have been recently renovated to create a 'perfect oasis for your relaxation, your peace and privacy. The environment is friendly. The renovation of the house was made using materials typical of the Maremma and in keeping the age of the …see more

from $111 / night

$774 / week

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from $111 / night

36

Vacation villa with shared pool in Roccastrada

Province of Grosseto / Roccastrada

7 20 7 nights min

  • 7 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Ghiandaia is an extremely attractive property surrounded by huge grounds (approximately 30 hectares of land) located in the heart of the Maremma region, the wildest area of Southern Tuscany. It was acquired by a renowned Swiss film-maker who fell in love with the bea …see more

from $1,036 / night

$7,254 - $15,491 / week

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from $1,036 / night

12

Roccastrada Vacation apartment rental

Province of Grosseto / Roccastrada

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
Do you want to discover and experience the real Tuscany? Perfect! You are in the right place: Roccastrada is the typical village in the heart of Maremma, where you can enjoy its flavors, landscapes, its rhythms and in autonomy. From here you can visit: Cities and towns: …see more

from $62 / night

$430 / week

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from $62 / night

14

Home rental in Roccastrada with swimming pool

Province of Grosseto / Roccastrada

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Federica is located in the countryside of the Maremma area near Grosseto, only 5 minutes from the village of Roccastrada, in southern Tuscany, an area that reaches out from the province of Siena to the sea. The house has been divided into two apartments, one downst …see more

from $272 / night

$1,900 - $3,929 / week

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from $272 / night

19

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Pet friendly
"Poggiolo", 3-room house 55 m2, on the ground floor. Rustic furnishings: living/dining room with 1 sofabed and satellite TV. Exit to the garden. 1 double bedroom. 1 small room with 1 bed and 1 pull-out bed. Kitchenette (oven, dishwasher). Shower/bidet/WC. Garden. Barbec …see more

from $57 / night

$396 / week

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from $57 / night

19

Roccastrada Vacation home rental

Province of Grosseto / Roccastrada

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Pet friendly
5-room house 120 m2, on the ground floor, rustic and tasteful furnishings: large living/dining room with open-hearth fireplace. Exit to the terrace. Lounge with 1 double sofabed and satellite TV (flat screen), DVD. 1 double bedroom with shower/bidet/WC. 1 double bedroom …see more

from $150 / night

$1,049 / week

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from $150 / night

17

Vacation home rental

Province of Grosseto / Roccastrada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly
"Casale Ulisse", 4-room house 90 m2 on 2 levels. Rustic furnishings: living/dining room with 1 double sofabed, open-hearth fireplace and dining table. Exit to the veranda. 1 room with 2 beds. Exit to the garden. Open kitchen (4 hot plates, oven, dishwasher, electric cof …see more

from $142 / night

$989 / week

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from $142 / night

13

Roccastrada Vacation home rental

Province of Grosseto / Roccastrada

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Pet friendly
2-room house 55 m2 on 2 levels, on the ground floor. Rustic and cosy furnishings: kitchen-/living room (4 hot plates, oven, dishwasher, microwave, electric coffee machine, Capsules for coffee machine (Nespresso)) with dining table, open-hearth fireplace, satellite TV an …see more

from $45 / night

$310 / week

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from $45 / night

8

Roccastrada Vacation studio rental

Province of Grosseto / Roccastrada

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Pet friendly
"Casale Belvedere", 1-room house 33 m2, on the ground floor. Comfortable furnishings: open living room with 1 double bed, shower/bidet/WC, satellite TV, hi-fi system and air conditioning. Kitchenette (4 hot plates, microwave, electric coffee machine). Garden 70 m2, lawn …see more

from $96 / night

$671 / week

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from $96 / night

22

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Pet friendly
"CASALE FONTE", 4-room house 100 m2 on 2 levels, on the ground floor. Comfortable furnishings: living/dining room with 1 double sofabed, open-hearth fireplace, satellite TV, hi-fi system and air conditioning. 1 double bedroom with shower/bidet/WC and air conditioning. 1 …see more

from $182 / night

$1,273 / week

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from $182 / night

18

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
3-room house 80 m2, on the ground floor. Renovated, tasteful and cosy furnishings: large living room with 1 double sofabed and TV (flat screen). Exit to the loggia. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hot plates, oven, dishwasher, microwave) with dining …see more

from $122 / night

$851 / week

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from $122 / night

32

Vacation villa in Roccastrada

Province of Grosseto / Roccastrada

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Child friendly
Enjoy views of the Tuscan landscape while also being just a short distance from the Maremma Coast when you stay at Villa Marchesa, Maremma Coast,Tuscany. Get the best of both worlds - the hills and the sea from this large and newly built mansion retreat. Ideal as a loca …see more

from $1,714 / night

$12,000 - $22,080 / week

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from $1,714 / night

28

Vacation home in Roccastrada

Province of Grosseto / Roccastrada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Pet friendly
5-room semi-detached house 100 m2 on 1st floor. Simple and rustic furnishings: large entrance hall with separate WC. Upper floor: living/dining room with TV. Exit to the balcony. 2 double bedrooms. 1 room with 2 beds. Kitchen (oven) with dining table. Bath/bidet/WC. Bal …see more

from $58 / night

$404 / week

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from $58 / night

34

Vacation villa in Roccastrada

Province of Grosseto / Roccastrada

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
The opportunity to tour Tuscany and also visit the sea is possible for those who visit the impressive Villa Maremmana, Maremma Coast, Tuscany. Located in the Maremma region of Tuscany, it is less than 30 minutes from the beaches, but it is also set within a private 1,20 …see more

from $1,371 / night

$9,600 - $16,800 / week

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from $1,371 / night

19

Vacation villa rental

Province of Grosseto / Roccastrada

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Outside A beautiful wrought iron gate welcomes guests of Casa this property and places it in an attractive avenue of cypress trees. this property a charming detached house in a quiet hillside with panoramic views of the unspoilt countryside of Maremma, is at your dispos …see more

from $331 / night

$692 - $2,320 / week

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from $331 / night

24

Roccastrada Vacation home rental

Province of Grosseto / Roccastrada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
3-room house 60 m2 on 2 levels, on the ground floor. Rustic furnishings: living room with 1 sofabed, dining table and satellite TV (flat screen), DVD. Exit to the garden. 1 double bedroom with panoramic window with 1 french bed (140 cm). Open kitchen (4 hot plates, oven …see more

from $113 / night

$791 / week

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from $113 / night

19

Vacation villa accommodation

Province of Grosseto / Roccastrada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Owner's description:Outside On a quiet area near the town of Roccastrada, the villa is an extraordinary luxury retreat, surrounded by olive grove and forest. Country house "this property", detached, renovated, surrounded by trees. 5 km from the centre of Roccastrada, in …see more

from $247 / night

$843 - $1,734 / week

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from $247 / night

17

Torniella Vacation villa rental

Roccastrada / Torniella

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:Additional information:This is a beautiful 5 bedroom property located in Tuscany, Italy.This villa, in Monticiano, is a comfortable property sleeping 8 people.The property has 2 bathrooms.The villa offers superb accommodation, including modern luxuri …see more

from $378 / night

$1,484 - $2,646 / week

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from $378 / night

22

Roccastrada Vacation villa rental

Province of Grosseto / Roccastrada

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Owner's description:Outside this property 1 km from Roccastrada: It is situated in the Tenuta di Pietreto, surrounded by chestnut trees and holm oak trees. Panoramic position, approx 460 m above sea level. Working farm "this property". 35 km from the centre of Grosseto, …see more

from $371 / night

$843 - $2,600 / week

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from $371 / night

20

Villa rental in Roccastrada

Province of Grosseto / Roccastrada

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : A beautiful wrought iron gate welcomes guests of Casa Montorsi and places it in an attractive avenue of cypress trees. Montorsi a charming detached house in a quiet hillside with panoramic views of the unspoilt countryside of Marem …see more

from $377 / night

$1,176 - $2,638 / week

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from $377 / night