50 Best Vacation Rentals in Province of Grosseto - Holiday Lettings - Cabins

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Castiglione Della Pescaia
225 properties
Orbetello
160 properties
Grosseto
158 properties
Monte Argentario
133 properties
Scarlino
113 properties
Manciano
109 properties
Massa Marittima
74 properties
Pitigliano
66 properties
Follonica
63 properties
Sorano
61 properties
Capalbio
58 properties
Civitella Paganico
47 properties
Roccastrada
46 properties
Magliano in Toscana
37 properties
Seggiano
36 properties
Scansano
36 properties
Gavorrano
28 properties
Castel Del Piano
27 properties
Braccagni
26 properties
Roccatederighi
23 properties

Province of Grosseto

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1,812 Vacation rentals

(9) Very Good 

18

Seggiano Vacation villa rental

Province of Grosseto / Seggiano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Casa Olivastra is built on the ruins of an ancient convent on the edge of Val d'Orcia. An ideal base to visit some of the most attractive towns in Tuscany . The house has been architecturally designed so that each room has its own unique view &terrace.The illuminated po …see more

from $114 / night

$710 - $1,704 / week

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from $114 / night

(28) Excellent 

20

Vacation farmhouse in Saturnia

Manciano / Saturnia

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
Country house, 4 bedrooms en suite upstairs (1 king bedroom just aut the corner is available on demand with no air condition price not included), hall with fireplace, dining room and spacious kitchen downstairs.The house is surrounded by a paved floor with on the West s …see more

from $346 / night

$2,219 - $3,945 / week

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from $346 / night

13

Vacation apartment in Campese

Isola Del Giglio / Campese

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
The apartment is located 20 meters above the sea and there is always a pleasant air that rises from the bay. The house is reached from the coastal road with a flight of 70 steps or along with the car a road that ends with a parking spot on. The house has a beautiful vie …see more

from $124 / night

$865 / week

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from $124 / night

(1) Excellent 

35

Vacation cottage rental

Province of Grosseto / Vetulonia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Private garden
Charming detached stone house on the edge of the forest overlooking the sea. A peaceful place surrounded by nature. The view you can enjoy sea and Valley views is absolutely fantastic. It is accessed by a steep 200-metre concrete driveway and decidedly accessible to car …see more

from $99 / night

$692 / week

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avg. 55 minutes

from $99 / night

(1) Excellent 

21

Vacation home in Alberese

Province of Grosseto / Alberese

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
Small house of 40 square meters in the countryside in the area called "pre-park" dell'Uccellina, part of the district of Grosseto, a charming town in the Maremma Regional Park. The house is small but has a double bed room with ergonomic pocket sprung wardrobe 6 doors an …see more

from $68 / night

$433 - $494 / week

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avg. 1 hour 5 minutes

from $68 / night

14

Bagno Roselle Vacation townhouse rental

Grosseto / Bagno Roselle

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Three apartments for rent surrounded by greenery in the area of Roselle Archaeological Park, seven kilometres from the city of Grosseto. We are close to the major attractions of the Maremma Natural Park of Uccellina, the Archaeological Park of Vetulonia, the coastline o …see more

from $74 / night

$433 - $741 / week

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avg. 3 hours 2 minutes

from $74 / night

12

Farmhouse rental in Massa Marittima with shared pool

Province of Grosseto / Massa Marittima

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 18 mi
  • Swimming pool
of about 60 square meters. a kitchen, a large master bedroom, a single room with three beds and more services outside court bed. Equipped with table, chairs, umbrella and grill for lunch or dinner outside. Ground floor. Possibility of access to the two swimming pools, r …see more

from $74 / night

$433 - $1,013 / week

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from $74 / night

(4) Very Good 

14

Vacation apartment rental

Manciano / Saturnia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
In the heart of the Tuscan Maremma, independent apartment, light, exactly in front of the splendid Terme di Saturnia and a few hundred meters from the Mill Falls. Living room with fireplace and fully equipped kitchen corner, TV and comfortable sofa bed for one person, d …see more

from $99 / night

$556 - $680 / week

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avg. 1 hour 45 minutes

from $99 / night

(1) Excellent 

17

Pitigliano Vacation home rental

Province of Grosseto / Pitigliano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
The House is located in the courtyard of a medieval castle renovated by Sangallo in ' 500, with travertine well and loggia. The size is romantic and charming, at the Centre of the town but in a separate context and devoid of machinery. The House is completely renovated, …see more

from $62 / night

$309 / week

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from $62 / night

22

Vacation home with shared pool in Roccalbegna

Province of Grosseto / Roccalbegna

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 45 mi
  • Swimming pool
Noce on the Il Poderone development, is a modern home built in a traditional Tuscan style, set in the peaceful, beautiful Tuscan hills. The house (the centre house in a row of three), has two bedrooms, and two bathrooms. The fully equipped kitchen includes a washing mac …see more

from $100 / night

$694 - $1,009 / week

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from $100 / night

14

Cottage accommodation in Monte Argentario

Province of Grosseto / Monte Argentario

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Argentario romantic cottage is surrounded by nature, and a panoramic garden in the most unspoiled area of Argentario. Enjoy the stunning view of the Mediterranean and discover the private footpath to the sea. Located on the side of a mountain by the sea, Monte Argentar …see more

from $321 / night

$2,242 - $2,989 / week

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from $321 / night

(19) Very Good 

22

Vacation apartment in Punta Ala

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Suite Description: Suite (private) 50 sq. approximately inserted into the Residence Hotel (RTA) called "Golf Hotel Punta Ala" (4 stars). Two rooms with 5 beds, consisting of living area with TV and kitchenette, refrigerator, 1 sofa bed, 1 pull-out bed, double bedroom wi …see more

from $89 / night

$618 - $2,840 / week

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from $89 / night

21

Villa rental in Roccatederighi

Province of Grosseto / Roccatederighi

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 39 mi
  • Child friendly
  • Pet friendly
The House is 500 metres from the Centre of the village on the hill above it, with a large veranda. The House is equipped with all the amenities: washing machine, dishwasher, gas cooker, fridge, and central heating and fireplace, tv, freezer. Bedrooms on the upper floor: …see more

from $62 / night

$334 - $593 / week

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avg. 2 hours 23 minutes

from $62 / night

15

Vacation apartment in Pitigliano

Province of Grosseto / Pitigliano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 58 mi
  • Child friendly
Lovely apartment consists of 2 bedrooms, 2 bathrooms, one with shower, spacious living room with fireplace and kitchenette. Centrally located adjacent to the Orsini palace overlooking the Medici aqueduct and the valley below. It is 2 km from the spas of Sorano, 22 km fr …see more

from $87 / night

$519 / week

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from $87 / night

22

Roccalbegna Vacation apartment rental

Province of Grosseto / Roccalbegna

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 50 mi
  • Child friendly
  • Pet friendly
The property is located in the hills of Maremma Roccalbegna resorts Triana province of Grosseto a private villa and private with the apartment of 3 double bedrooms services independent entrance lounge kitchen furnishings comfort large garden ample parking facilities hos …see more

from $50 / night

$371 - $1,297 / week

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avg. 2 hours 37 minutes

from $50 / night

13

Apartment rental in Porto Ercole

Monte Argentario / Porto Ercole

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
Bright apartment in Porto Ercole feniglia 2km from the sea and other beautiful bays. Recently completely renovated, ground floor consists of 2 bedrooms, sitting room with sofa and TV, equipped kitchenette and bathroom with doccia.tutte rooms have windows and the larger …see more

from $124 / night

$741 - $1,390 / week

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from $124 / night

32

Villa rental in Monte Argentario with shared pool

Province of Grosseto / Monte Argentario

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Interiors This stylish seafront villa features a simple, elegant and maritime atmosphere. The spacious living room, with its walls made of local stones, is separated by a fireplace, situated in the center. On one side there is the sitting area with a comfortable masonry …see more

from $626 / night

$4,383 - $8,765 / week

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from $626 / night

24

Vacation apartment in Sorano

Province of Grosseto / Sorano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Delicious home surrounded by nature in Tuscany farmhouse carefully restored stone, the charm of grit floors surrounded by Greek and Florentine ceilings, antique bricks and chestnut wood beams. Near the baths of Sorano, San Filippo, of Vignome Bagni and Saturnia. Village …see more

from $44 / night

$272 - $346 / week

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Responds fast!
avg. 1 hour 12 minutes

from $44 / night

23

Vacation home in Isola Del Giglio

Province of Grosseto / Isola Del Giglio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Independent house completely renovated (inside and out) one year ago '. It is located inside a residence absolutely pedestrian. The only access is by foot, the car is parked about 200 m from the house (upstream) and the sea, accessible by opening the gate with a key giv …see more

from $247 / night

$1,729 / week

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from $247 / night

22

Vacation farmhouse with swimming pool in Montemassi

Province of Grosseto / Montemassi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
Diga apartment features a quiet bedroom with a peaceful valley and lake views. It has a private entrance, private bath and private terrace with 2 chairs and outdoor table, The bathroom is equipped with sink, toilet and shower. This is a simple, yet very comfortable cozy …see more

from $61 / night

$402 - $482 / week

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Responds fast!
avg. 1 hour 55 minutes

from $61 / night

18

Vacation cottage in Montieri

Province of Grosseto / Montieri

2 3 nights min

  • Sleeps 2
  • 3 nights min
  • Nearest beach 43 mi
  • Pet friendly
Podere Prati is situated between Siena and Follonica in the so called "Colline Metallifere"/"Alta Maremma". You choose the right place if you are looking for a special place well off the beaten tourist track, and yet not far from great culture and the coast of the Tyr …see more

from $71 / night

$488 / week

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from $71 / night

(1) Excellent 

32

Townhouse rental in Scarlino

Province of Grosseto / Scarlino

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
The Magnolia is an apartment of 65 square meters located in an ancient village of 1800 in Tuscany, away from the frenetic pace of the city; an apartment, therefore, ideal for a relaxing vacation and quiet, surrounded by forests of cork oaks and chestnut trees with trail …see more

from $62 / night

$297 - $556 / week

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from $62 / night

17

Marina di Grosseto Vacation studio rental

Grosseto / Marina di Grosseto

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
completely renovated apartment (in 2016), surrounded by pine trees condominium, ideal for the sea and for excursions in the beautiful Tuscan Maremma. Easy to reach by car or public transport, it is located a few meters from the sea. The studio of about 20 square meters, …see more

from $44 / night

$303 / week

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avg. 59 minutes

from $44 / night

7

Vacation villa in Manciano

Province of Grosseto / Manciano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Peschiere in Maremma, a spacious and historic farmhouse on top of its own hill in the vicinity of Terme di Saturnia, is an exceptional place for accommodation, meetings and events. It located at the end of a long driveway in a large garden and is surrounded by his w …see more

from $62 / night

$371 / week

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from $62 / night

12

Vacation villa in Ansedonia

Orbetello / Ansedonia

4 7 14 nights min

  • 4 bedrooms
  • Sleeps 7
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Villa in Ansedonia near Argentario, in the province of Grosseto. Develops into a main body composed of living room, dining room, kitchen and a small single bedroom on the ground floor and two bedrooms with bathrooms on the first floor plus a dependance composed of one d …see more

from $353 / night

$2,470 - $7,656 / week

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from $353 / night

21

Scansano Vacation apartment rental

Province of Grosseto / Scansano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Ask about pets
The bright apartment of about 110 square meters, on two floors (with internal staircase connecting the two floors), is located in the complex of the ancient Convent of Petreto on a hill about 1.5 km from the village of Scansano. The convent, built in 1300 and under the …see more

from $74 / night

$433 - $1,556 / week

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from $74 / night

(12) Excellent 

22

Finca rental in Grosseto with shared pool

Province of Grosseto / Grosseto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
Apartment in ground floor with veranda part along with other 7 apartments in a farmhouse in the countryside. Quiet suitable for both families and couples or friends. Nearby popular attractions of Maremma, bathing, archaeological sites, landscapes and sports. …see more

from $124 / night

$556 - $926 / week

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Responds fast!
avg. 3 hours 47 minutes

from $124 / night

(2) Excellent 

15

Vacation finca in Montiano

Magliano in Toscana / Montiano

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
If you're looking for a secluded place, where it is not easy to get there (3 km of gravel road) on the edge of a wood (maquis) of 8000 hectares where you can walk by bike or on foot where a surreal peace research, eat the foods natural products on the farm, where there …see more

from $124 / night

$865 / week

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from $124 / night

(1) Excellent 

31

Vacation b&b accommodation

Province of Grosseto / Follonica

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
The White House is located in the center of Follonica, just steps from the sea and pine forests, in Via Cristoforo Colombo 25. Recently renovated, spread over three floors, has 4 bedrooms tastefully decorated and feature a color theme ( blue, orange, green, purple). E ' …see more

from $81 / night

$556 - $4,322 / week

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from $81 / night

29

Pitigliano Vacation home rental

Province of Grosseto / Pitigliano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
Zaccheo's House is a very beautiful house full of history and charm, situated in the oldest part of the historical center of Pitigliano, near the Jewish ghetto. Beautifully restored with old and original materials has been furnished by the owners with antique furniture …see more

from $161 / night

$964 / week

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from $161 / night

(1) Excellent 

20

Vacation villa with golf nearby in Giannella

Orbetello / Giannella

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
"Holiday Villa for SHORT and LONG term rental ♥ LOCATION ♥ in Tuscany ☺ at1h train to ☼Rome ☼Florence ♥ FEATURES ♥ 12 sleeps. ☼3 bedrooms, ☼2 bathrooms, Speed Unlimited Wi-Fi, Fireplace, Private Parking, Fully equipped Garden, Airco, Heating, Washing machine, Dishwa …see more

from $202 / night

$1,210 - $1,988 / week

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from $202 / night

24

Vacation apartment with swimming pool in Porto Ercole

Monte Argentario / Porto Ercole

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
DESCRIPTION This stylish and luxury swimming pool villa for rent is swathed in greenery, on the top of one of the most beautiful hills of Argentario. The property overlooks Porto Ercole fortress and Marina, as well as the blue Mediterranean sea. The swimming pool is …see more

from $2,283 / night

$15,978 / week

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from $2,283 / night

(6) Very Good 

Certificate of Excellence

13

Vetulonia Vacation townhouse rental

Province of Grosseto / Vetulonia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Located in the village of Etruscan Vetulonia, 320 m high, located about 20 minutes by car from the splendid sea of Castiglione della Pescaia (Grosseto), and 30 minutes from the natural park of maremma, x short rent week or even x week.end only. Recently renovated apartm …see more

Certificate of Excellence

from $56 / night

$420 / week

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Responds fast!
avg. 3 hours 51 minutes

from $56 / night

6

Vacation home in Elmo

Sorano / Elmo

3 5 5 nights min

  • 3 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Private garden
Our house offers peace, relaxation and nature, without having to give up your claims. The Rustico is an old stone house that has been restored in traditional Tuscan style. On the terrace with a stunning view, (on the horizon of the sea), the first Cafè be enjoyed. The a …see more

from $61 / night

$424 / week

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from $61 / night

(7) Excellent 

8

Batignano Vacation tower rental

Province of Grosseto / Batignano

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This ancient building dates back to the Middle Ages, when it was used in the defense of the village. The house is equipped with an original raised fireplace. The arched entrance to the city was destroyed during World War II, but you can still enjoy the part that will be …see more

from $63 / night

$432 / week

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from $63 / night

(4) Excellent 

18

B&b rental in Massa Marittima

Province of Grosseto / Massa Marittima

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Massa Marittima is a beautiful medieval town in the hills of the Tuscan Maremma, close to the most beautiful beaches of the Tyrrhenian Sea and Lake dell'Accesa, with a cool and windy climate even in summer In the historic center you will find HOUSE PIA, the Palazzo Pann …see more

from $87 / night

$568 - $741 / week

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from $87 / night

14

Grosseto Vacation guest house rental

Province of Grosseto / Grosseto

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
The apartment is in the walled part of the center of Grosseto. The railway station is a ten minute walk and there is a car park three minutes from the apartment. Buses are many and frequent to the beach, 20 minutes away or Florence and Sienna about an hour away.The apar …see more

from $44 / night

$272 / week

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Responds fast!
avg. 2 hours 1 minutes

from $44 / night

24

Vacation b&b in Civitella Marittima

Province of Grosseto / Civitella Marittima

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 40 mi
  • Air conditioning
  • Private garden
Violapo Cottage is a small country located in Civitella Marittima, in the province of Grosseto in the Valley that joins with the territory of Roccastrada, conveniently located services easy to find but at the same time well. The property offers 4 beds (2 + 2), with a su …see more

from $124 / night

$863 / week

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Responds fast!
avg. 38 minutes

from $124 / night

(1) Excellent 

24

Vacation farmhouse with shared pool in Montemassi

Province of Grosseto / Montemassi

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Swimming pool
Rocca Apartment features a quiet north oriented bedroom with a lovely country views from its terrace. It has a private entrance, a large private bathroom and terrace with an outdoor table and 2 chairs. The bathroom is equipped with sink, toilet, bidet and shower. This i …see more

from $61 / night

$424 / week

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Responds fast!
avg. 1 hour 55 minutes

from $61 / night

(1) Excellent 

27

Apartment rental in Gavorrano with golf nearby

Province of Grosseto / Gavorrano

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
IL NIDO is a delightful apartment (size 50 sq meters) completely and well restored according Tuscan style, located in the historical charming medieval hamlet of Gavorrano at High Maremma in Tuscany (South-west). Gavorrano is placed on the top of a hill (altitude of 273 …see more

from $52 / night

$358 - $642 / week

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from $52 / night