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

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Castiglione Della Pescaia
237 properties
Orbetello
150 properties
Monte Argentario
134 properties
Grosseto
134 properties
Scarlino
116 properties
Manciano
114 properties
Sorano
92 properties
Massa Marittima
72 properties
Capalbio
71 properties
Follonica
65 properties
Pitigliano
59 properties
Civitella Paganico
52 properties
Roccastrada
39 properties
Scansano
32 properties
Magliano in Toscana
32 properties
Gavorrano
27 properties
Braccagni
27 properties
Seggiano
27 properties
Castel Del Piano
25 properties
Arcidosso
22 properties

Province of Grosseto

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1,686 Vacation rentals

(2) Very Good 

21

Porto Santo Stefano Vacation villa rental

Monte Argentario / Porto Santo Stefano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Details (DE) Die Halbinsel Monte Argentario mit ihren beiden Badeorten Porto Ercole und Porto Santo Stefano, liegt an der südlichen Küste der Toskana, 150 km nördlich von Rom. Der Monte Argentario erhebt sich wie eine Insel aus dem Meer, und durch eine von zwei schmale …see more

from $118 / night

$703 - $1172 / week

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from $118 / night

19

Vacation home in Punta Ala

Castiglione Della Pescaia / Punta Ala

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Elegant and comfortable terraced house, surrounded by greenery, at 500m. from the sea in one of the most beautiful and magic of the Maremma coast ... PUNTA ALA! It 'a house of the 60's characterized by a very large window that makes the living room and the outdoor area …see more

from $166 / night

$1161 - $2612 / week

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from $166 / night

4

Albinia Vacation apartment rental

Orbetello / Albinia

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
At the Albegna river, just 200 meters from the beach, sits the lovely and spacious Casale del Breschi, a farmhouse which dates to the 18th century, when improvements of the Maremma and its coasts were part of the reformist policies of the Granduke Peter Leopold. The Cas …see more

from $481 / night

$3367 - $3773 / week

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Responds fast!
avg. 1 hour 12 minutes

from $481 / night

(1) Excellent 

40

Vacation hotel apartment in Puntone

Scarlino / Puntone

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The new structure created in the year 2015 and located along the seafront from Follonica door at Puntone di Scarlino offers apartments with two bedrooms with direct access to the beach. Excellent services: free wi-fi, laundry, LCD TV, kitchen complete with oven and dish …see more

from $93 / night

$390 - $1560 / week

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from $93 / night

13

Vacation private room in Rispescia

Grosseto / Rispescia

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
And LUMINIOSA LARGE MASTER BEDROOM WITH PRIVATE BATH IN A HOUSE NEAR THE HILL IN 10 MINUTES FROM GROSSETO, 15 MINUTES FROM THE MAREMMA PARK AND 20 MINUTES FROM THE SEA. CHESTNUT SOLID DOORS, WHITE FURNITURE, PARQUET, BRIGHT, 'QUIET' AND SILENCE. THE HOUSE IS ON TOP OF A …see more

from $46 / night

$317 / week

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from $46 / night

(1) Excellent 

8

Vacation apartment in Giannutri Island

Province of Grosseto / Giannutri Island

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
ISOLA DI GIANNUTRI 32 GRADINI DALL' ACQUA "casa lentisco" GIANNUTRI:Mare-Sole-Pesca-Trekking . LA PIU' VICINA AL MARE 18 Gradini dalla "Piazzetta"; 32 Gradini dall'acqua; L'ampio terrazzo alberato e fiorito domina la baia di Spalmatoio offrendo un q …see more

from $175 / night

$1219 / week

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avg. 2 hours 33 minutes

from $175 / night

(27) 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 $407 / night

$2090 - $3599 / week

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from $407 / night

(1) Excellent 

14

Vacation townhouse in Monte Argentario

Province of Grosseto / Monte Argentario

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on Silent Hill, although in urban centre, ground floor, sea view 2 storey building surface. 60sqm. 200 mt shopping centre. Embarkation for Islands to 200 meters. Beaches accessible walk in less than 3 minutes. Apartment fully furnished and recently refurbished …see more

from $117 / night

$813 - $894 / week

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avg. 3 hours 42 minutes

from $117 / night

100

Vacation villa with swimming pool, tennis court in La Pesta

Province of Grosseto / La Pesta

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 34 mi
  • Swimming pool
  • Child friendly
ExteriorThis grand villa lies in Maremma in an area of 1200 acres of protected nature reserve, enjoyed exclusively by the owner and their guests in absolute peace and tranquillity. Lounging by your glorious private swimming pool is true bliss and one of course must not …see more

from $1393 / night

$9286 - $11608 / week

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from $1393 / night

(2) Excellent 

13

Vacation home rental

Province of Grosseto / Monte Argentario

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
The studio is located on the promontory of Monte Argentario and enjoys a beautiful view of the sea and islands Sea Wonder House is a studio of 40 square meters divided in its interior by a wall system, which creates two separate bedrooms. Bathroom with shower . The hous …see more

from $82 / night

$523 / week

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avg. 1 hour 33 minutes

from $82 / night

(1) Excellent 

20

Home rental in Monte Argentario

Province of Grosseto / Monte Argentario

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
This is an ideal solution to enjoy a few days relaxing. THE HOUSE ; A bedroom with bathroom, small but cozy, overlooking the veranda and a 100 sqm garden completely private and exclusive, with a full view of the sea and islands. The small structure has an indoor area bu …see more

from $59 / night

$410 - $645 / week

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Responds fast!
avg. 1 hour 33 minutes

from $59 / night

18

Farmhouse rental in Roccalbegna with swimming pool

Province of Grosseto / Roccalbegna

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 58 mi
  • Swimming pool
  • Child friendly
Ground floor apartment: living room with fireplace, dining room with large table for 13 people and a large wood burning stove, a kitchen, a large porch furnished with tables, chairs and a sofa, a double bedroom with bathroom with bath and shower, a bedroom with a small …see more

Pricing unknown

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Pricing unknown

15

Vacation home in Giannutri Island

Province of Grosseto / Giannutri Island

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
Large studio suitable for receiving 4 people with kitchenette and bagno.Ampio terrace on the rocks. Situated at the entrance of the complex and therefore particularly suitable for those seeking tranquility. Located with good exposure allowing to enjoy the sun until suns …see more

from $175 / night

$1219 / week

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Responds fast!
avg. 2 hours 37 minutes

from $175 / night

(1) Very Good 

16

Vacation apartment in Scarlino

Province of Grosseto / Scarlino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Ask about pets
Lotus is an apartment of about 45 sq.m located in an ancient village of 1800 in the Tuscan Maremma and away from the fast pace of the city; an apartment suited to a vacation of rest and relaxation, surrounded by forests of cork oaks and chestnut trees with trails for tr …see more

from $47 / night

$256 - $424 / week

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from $47 / night

24

Vacation villa in Porto Ercole

Monte Argentario / Porto Ercole

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This amazing villa is located in Porto Ercole, a village in the promontory of Monte Argentario, Tuscany, about 150 km south of Florence and 35 km south of Grosseto. The promontory stretches towards the Tyrrenian sea in correspondence of the islands of Giglio and Giannut …see more

from $465 / night

$3250 - $8125 / week

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from $465 / night

8

Vacation home in Campese

Isola Del Giglio / Campese

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Comfortable apartment on the first floor balcony adjacent to the center for diving Deep Blue Diving College of Giglio Campese. The same is composed of a double room with double bed, a cameta double with two beds that can be coupled to form another double bed, living roo …see more

from $93 / night

$650 - $1567 / week

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from $93 / 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 $70 / night

$407 - $1556 / week

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from $70 / night

15

Punta Ala Vacation apartment rental

Castiglione Della Pescaia / Punta Ala

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
Apartment on the first floor of the Residence I Boboli with two balconies (in the living room and in the large bedroom) overlooking the beautiful beaches of Punta Ala and the islands of Elba, Cerboli, Palmaiola and on clear days, Goatherd. All available to guests, the a …see more

from $47 / night

$326 / week

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from $47 / night

31

Vacation townhouse in Montiano

Province of Grosseto / Montiano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 18 mi
  • Child friendly
lovely new apartment in Montiano (four-family new homes at the foot of the country), in the Maremma Park, 15 minutes from Talamone (Argentario). sea ​​view, open space living room with kitchenette, fireplace, terrace, small garden, private parking, pool. bathroom with t …see more

from $93 / night

$650 / week

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from $93 / night

16

Vacation apartment in Principina a Mare

Province of Grosseto / Principina a Mare

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
The apartments ' Lobster ' Street are situated on the ground floor with outdoor space and large covered veranda equipped with table and chairs to dine or just relax surrounded by centuries-old pine woods. The apartments consist of: living/dining room with extra bed and …see more

from $151 / night

$553 - $1276 / week

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from $151 / night

8

Vacation apartment in Orbetello

Province of Grosseto / Orbetello

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
in the limited traffic area in the center bar restaurants all services. bike path to the beach or boat. all locations easily accessible Maremma hinterland. a few kilometers from the embarkation to the Tuscan archipelago. small apartment but well structured consists of l …see more

from $76 / night

$523 - $581 / week

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from $76 / night

(1) Very Good 

6

Vacation home in Isola Del Giglio

Province of Grosseto / Isola Del Giglio

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Chalet on 2 floors località Giglio Porto, with large living room, kitchen, bathrooms large terrace and balcony overlooking the sea, just minutes from beautiful beaches. Fully equipped House fresh and ideal for families and group of friends. wonderful hiking or sea islan …see more

from $140 / night

$813 - $1219 / week

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from $140 / night

13

Vacation guest house with shared pool in Ribolla

Province of Grosseto / Ribolla

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
the Borgofontelupo Farmhouse is situated on a lush hillock adjoining the old Renaissance dam near the river Bruna, contained in a typical rural environment, between olive groves and vineyards set above rest of the Tuscan Maremma landscape, crossed by paths and streams a …see more

from $59 / night

$407 / week

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from $59 / night

18

Vacation apartment with shared pool in Buriano

Province of Grosseto / Buriano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
For rent beautiful apartment in Tuscany, 10 km from Castiglione della weir, ideal for leisure outside the city, combines the quiet of the countryside to the proximity of the sea to form the perfect combination then. Private parking included. Garden with barbecue with ad …see more

from $70 / night

$685 / week

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from $70 / night

5

Vacation farmhouse with shared pool in Grosseto

Province of Grosseto / Grosseto

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Razza del Casalone is an elegant farmhouse along the coast in Maremma Toscana, surrounded by a 2-hectare park and with a private swimming pool, located just 10 km from the seaside. The main building in the farmhouse was built in the 18th century and contains 5 id …see more

from $94 / night

$656 / week

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Responds fast!
avg. 2 hours 50 minutes

from $94 / night

(2) Good 

45

Vacation hotel apartment with shared pool in Follonica

Province of Grosseto / Follonica

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Small tourist complex divided into cottages, just 500 metres from the sea. The apartments are all located on the first floor, except one, all have a splendid terrace overlooking the sea or pine forest. The apartment is composed as follows: terrace, closed with wooden …see more

from $59 / night

$407 - $1509 / week

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Responds fast!
avg. 2 hours 41 minutes

from $59 / night

(3) Very Good 

9

Vacation apartment in Orbetello

Province of Grosseto / Orbetello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Two rooms suitable for couples and/or families with a child arrives at the beach without crossing the road, clean sea, with sea floor it degrades very slowly and the downstairs offers a bar service and the possibility to have lunch on the beach ...Boat trip on the lagoo …see more

from $71 / night

$528 - $1055 / week

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Responds fast!
avg. 3 hours 23 minutes

from $71 / night

7

Giannutri Island Vacation penthouse rental

Province of Grosseto / Giannutri Island

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
Unica-fantastic Studio on cliffs composed of large bedroom-kitchen-bathroom and terrace with disimpegno.nel which are the two extra beds. the penthouse is the last of the then practically isolated.In addition, given the location of the last eê who loses the Sun unique e …see more

from $175 / night

$2032 / week

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from $175 / night

(5) Excellent 

12

Vacation apartment in Scarlino

Province of Grosseto / Scarlino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Ask about children
The Artist's House is located in the center of Scarlino, a medieval village on a hill overlooking the coast of Tuscany Maremma, an area rich in history and Etruscan sites, artistic and natural beauty. The port is just a few kilometers from the center. A few steps from t …see more

from $59 / night

$407 - $650 / week

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from $59 / night

(1) Excellent 

15

Vacation villa with golf nearby in Massa Marittima

Province of Grosseto / Massa Marittima

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 18 mi
  • Child friendly
Semi-detached cottage in the heart of Maremma, Massa Marittima in 100 meters walk from the old town and the Piazza del Duomo. Private entrance and parking place, a residence surrounded by greenery and surrounded by greenery. From the kitchen and the bedroom look over t …see more

from $58 / night

$270 - $375 / week

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from $58 / night

15

Vacation home in Porto Ercole

Monte Argentario / Porto Ercole

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Argentario family villa rental with sea views – From its elevated position, this delightful family villa with pool commands far reaching views over the stunning bay of Porto Ercole and the Tyrrhenian sea, just one mile away. Most of Argentario's sandy beaches and beach …see more

from $351 / night

$2457 - $5694 / week

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from $351 / night

(4) Excellent 

14

Vacation apartment in Principina a Mare

Province of Grosseto / Principina a Mare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
L'appartamento molto carino ha una meravigliosa vista sulla pineta verso il Parco naturale della Maremma che confina con Principina. E' così composto: oltre al bagno con doccia c'è una soggiorno con televisore e angolo cottura attrezzato e una camera a tre letti. Sia la …see more

from $59 / night

$314 - $929 / week

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from $59 / night

8

Vacation home accommodation

Orbetello / Giannella

4 2 7 nights min

  • 4 bedrooms
  • Sleeps 2
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Ask about pets
House with four rooms and 3 bathrooms, quiet and suitable for families with childrens. Tuscany Maremma, land seafront, in a wild and untouched area portion of an historical stone farmhouse which the manor is a tower of Spanish origin and has been built on 15th century. …see more

from $199 / night

$1393 - $2554 / week

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from $199 / night

24

Porto Ercole Vacation villa rental

Monte Argentario / Porto Ercole

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
DESCRIPTION This Argentario super luxury villa for rent with swimming pool features a great location: a green hill overlooking the sea, Feniglia beach and three historic fortresses (Forte Filippo, Forte Stella and the Spanish Fortress). Just above Porto Ercole …see more

from $1990 / night

$13929 - $16390 / week

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from $1990 / night

(2) Very Good 

9

Vacation apartment in Castiglione Della Pescaia

Province of Grosseto / Castiglione Della Pescaia

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
A tangerine tree in the garden gives the name to this flat. It is a two-room home of about 35sqm which was totally restored in 2010 and which was once part of our nearby home. You only have to go down a few steps of a staircase from Via Cervino to enter the flat. That …see more

from $117 / night

$523 - $1057 / week

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Responds fast!
avg. 1 hour 55 minutes

from $117 / night

(1) Excellent 

8

Follonica Vacation home rental

Province of Grosseto / Follonica

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Child friendly
In just 10 minutes you are on the beautiful seafront of Follonica! You will reach it on foot or by bicycle through a mostly pedestrian-bike path. Behind the house opens a campaign characterized by rolling hills, ideal for walking and mountain biking. You will like my ac …see more

from $64 / night

$407 - $813 / week

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from $64 / night

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 $69 / night

$480 / week

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Responds fast!
avg. 1 hour 22 minutes

from $69 / night

(5) Good 

17

Batignano Vacation farmhouse rental

Province of Grosseto / Batignano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
The agriturismo Poggio Falco has well-kept accommodation with double rooms with bathroom, private entrance and private garden. Possibility of lunch in the shade of the forest adjacent to the structure. Beautiful yoga room made of bales of straw, wood-fired oven for br …see more

from $47 / night

$325 - $1300 / week

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from $47 / night

(1) Excellent 

48

Vacation apartment with shared pool in Casale di Pari

Civitella Paganico / Casale di Pari

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Poggio alla Rocca is indicated by maremmaguide site as the best location of the Maremma-Tuscany: this apartment called Sughera along with other 4 is immersed in two nature reserves, with all the comfort and with an infinity pool "infinity" on the Tuscan collini Indepen …see more

from $235 / night

$1640 / week

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Responds fast!
avg. 52 minutes

from $235 / night

(1) Very Good 

22

Vacation apartment in Porto Ercole

Monte Argentario / Porto Ercole

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Lovely apartment located in a two-story building in the center of Porto Ercole. The apartment is fully equipped and provided with all comforts (washing machine, dishwasher, vacuum cleaner, air conditioning, 2 tv, etc.). Two bedrooms, one with a double bed and the other …see more

from $105 / night

$732 / week

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from $105 / night