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

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Castiglione Della Pescaia
253 properties
Orbetello
152 properties
Monte Argentario
139 properties
Grosseto
134 properties
Manciano
109 properties
Sorano
89 properties
Capalbio
84 properties
Scarlino
84 properties
Massa Marittima
72 properties
Pitigliano
50 properties
Follonica
44 properties
Civitella Paganico
42 properties
Roccastrada
39 properties
Magliano in Toscana
34 properties
Scansano
33 properties
Gavorrano
29 properties
Seggiano
27 properties
Arcidosso
24 properties
Castel Del Piano
23 properties
Braccagni
22 properties

Province of Grosseto

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1,719 Vacation rentals

(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 $393 / night

$2020 - $3478 / week

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from $393 / night

29

Vacation apartment in Punta Ala

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
Suite of 50 square meters. 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, 1 sofa bed, 1 pull-out bed, double bedroom with TV, a bathroom with two si …see more

from $72 / night

$501 - $2560 / week

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from $72 / night

(2) Excellent 

8

Vacation apartment in Santa Fiora

Province of Grosseto / Santa Fiora

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Interesting recently renovated apartment just steps from the historic center of a medieval village on the slopes of Mount Amiata. Fabulous panoramic view of Peschiera Aldobrandesca. Country quiet but very active, rich in many cultural activities, music and nature. In th …see more

from $57 / night

$393 / week

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from $57 / night

(15) Very Good 

23

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 of 50 square meters. 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, 1 sofa bed, 1 pull-out bed, double bedroom with TV, a bathroom with two si …see more

from $72 / night

$501 - $2560 / week

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from $72 / night

(3) Very Good 

20

Vacation apartment in Grosseto

Province of Grosseto / Grosseto

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
It is a comfortable and cosy Studio apartment is suitable for one or two people. In the main room is the sofa ready bed, a large wardrobe and shelf where to find books and guides. Big bathroom with shower and washing machine. The kitchen is separate and raised three ste …see more

from $34 / night

$234 / week

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from $34 / night

18

Follonica Vacation apartment rental

Province of Grosseto / Follonica

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
BLUE SKY is a cool and comfortable accommodation to the first floor of a terraced house 2 levels E 'consists of a' large bedroom with double bed and a bunk bed, a living room with sofa bed, kitchen and bathroom with shower. It has a spacious balcony where guests can din …see more

from $45 / night

$281 - $897 / week

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from $45 / night

(1) Very Good 

15

Apartment rental in Principina a Mare

Province of Grosseto / Principina a Mare

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Joy (32 sqm) apartments are located on the edge of the immense pine forest of Principina a Mare, just 1500 metres from the sea and 2,000 from the Mall, connected by a path shaded and illuminated in a beautiful Avenue. The apartments consist of: living/dining room with …see more

from $62 / night

$269 - $819 / week

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from $62 / night

(2) Very Good 

14

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 $113 / night

$674 - $1122 / week

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from $113 / night

(2) Very Good 

16

Vacation home in Follonica

Province of Grosseto / Follonica

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Pet friendly
L 'accommodation of the Sun is part of a structure, Holiday Home Arzilli, offering accommodation 50 meters from the sea, in a pedestrian area, with the opportunity to use the public beach that the beaches, in close proximity to shady pine forests, with large children's …see more

from $49 / night

$337 - $561 / week

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from $49 / 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 $449 / night

$3141 - $7853 / week

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from $449 / 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 $90 / night

$374 - $1496 / week

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from $90 / night

9

Apartment rental in Rispescia

Grosseto / Rispescia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Rispescia (GR) at ten minutes from the sea and the natural park of Maremma. Apartment in Villa, located on the first floor with two bedrooms with a double bed and two single beds plus sofa bed. Bathroom with shower, equipped kitchenette including more tv lounge with ter …see more

from $68 / night

$472 / week

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from $68 / night

28

Vacation townhouse in Follonica

Province of Grosseto / Follonica

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The apartment is on the first floor of a small building. Large and bright, is formed of a double bedroom, a living room with sofa bed and possibly up to two extra beds, a kitchen with TV, microwave and two refrigerators, bathroom with shower and washing machine. On the …see more

from $45 / night

$312 / week

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from $45 / night

17

Vacation home in Isola Del Giglio

Province of Grosseto / Isola Del Giglio

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Ask about pets
Like a pearl in an oyster, the small Giglio isle lies cradled by warm blue seas in the southern corner of the Tuscan Archipelago, 50 km south of Elba and 15 km from the mainland connected by ferries. The owners of Villa Calypso want to offer the guest a real unforgatta …see more

from $353 / night

$2468 / week

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from $353 / night

18

Vacation apartment rental

Province of Grosseto / Scarlino

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
The House of Artist Plus is an independent apartment located in the same house and studio of the owners, the artist Mauro Corbani and his wife Laura, in the medieval village of Scarlino, stands on a hill overlooking the coast of Tuscany Maremma. The guest accommodation …see more

from $90 / night

$539 - $786 / week

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from $90 / night

26

Vacation farmhouse in Saturnia

Manciano / Saturnia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Our mission (low cost – high nature) is to offer very attractive prices due to basic (spartan) furniture for a nice vacation based on semplicity, relax and nature. with many attractions in the nearby. The two farmhouses (Il Monte and il Casaletto) are surrounded by am …see more

from $78 / night

$561 / week

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from $78 / night

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 $57 / night

$393 - $617 / week

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from $57 / night

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 $169 / night

$1178 / week

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from $169 / night

(1) Excellent 

13

Cala Piccola Vacation villa rental

Monte Argentario / Cala Piccola

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
****Included in the price FREE ACCESS for 4 PEOPLE TO THE PRIVATE BEACH where you can make use of a beach umbrella, two deck chairs and two beach beds Dear Guests, We are delighted to present this lovely villa located on the most extreme point of the Argen …see more

from $101 / night

$561 - $1683 / week

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from $101 / night

(1) Excellent 

12

Vacation bungalow in Gavorrano

Province of Grosseto / Gavorrano

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
The House "Rondine" for 2 persons, is located on the gentle hills, surrounded by Cypress. The site ' La Villa' covers 24 ha, pasture farmlands, forest, olive trees, vines and many fruit trees such as apricots, figs and cherries. "La Villa" has its own source. The neare …see more

from $85 / night

$561 - $740 / week

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from $85 / night

(6) Very Good 

24

Porto Ercole Vacation villa rental

Monte Argentario / Porto Ercole

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This apartment, named "I Gabbiani", it's on first floor of our Villa. It offers two double rooms and can welcome 4 guests.(max6) The master room, with ensuite small bathroom with shower, opens onto the furnished terrace looking to the sea. It is equipped with air condi …see more

from $225 / night

$1401 - $3419 / week

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from $225 / night

21

Vacation home with swimming pool in Cura Nuova

Province of Grosseto / Cura Nuova

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Wonderful independent farmhouse, surrounded by olive trees but about 7 minutes from the sea with large sandy beaches and surrounded by pine trees, where accept our furry friends. We rent from May 1. 1 double room and two smaller rooms with single beds and a half, living …see more

from $51 / night

$334 - $490 / week

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from $51 / night

12

Follonica Vacation b&b rental

Province of Grosseto / Follonica

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 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 $73 / night

$449 - $785 / week

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from $73 / night

20

Vacation apartment rental

Province of Grosseto / Castiglione Della Pescaia

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.15 mi
  • Child friendly
The apartment is in the centre of Castiglione della Pescaia, a lovely Tuscan village. It is about 100 m from the beach and has a view on the harbour and a view on the castle. In front of the house, on the hill, there's a typical terraced garden, with a beautifu …see more

from $57 / night

$393 - $897 / week

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from $57 / night

(5) Excellent 

24

Vacation farmhouse in Sorano

Province of Grosseto / Sorano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This recently restored portion of a farmhouse and its outbuilding are set in an idyllic and tranquil position along the gentle slopes at the feet of Mount Amiata in the south of Tuscany, near the Lazio border. The area abounds with historic towns (like Sorano, Sovana an …see more

from $135 / night

$674 - $1784 / week

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from $135 / night

(5) Very Good 

13

Vacation apartment in Roccamare

Castiglione Della Pescaia / Roccamare

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Suitable for children age 5+
Apartment in locality Rocchette, detached cottage nestled in the pine forest of Roccamare, a few kilometres from Castiglione della Pescaia to the beautiful coast that leads to point it. Consisting of two bedrooms, kitchen, bathroom, veranda, garden and brick box with ho …see more

from $57 / night

$393 / week

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from $57 / night

(1) Excellent 

10

Scarlino Scalo Vacation apartment rental

Scarlino / Scarlino Scalo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
La Struttura è composta da 2 appartamenti composti da camera da letto, soggiorno con divanoletto a 3 posti e angolo cottura, bagno e verande. 5000 m di giardino,piscina ( 17x6, alta 1.50), pargheggio interno e possibilità di fare il barbecue. A 6 chilometri da Follonica …see more

from $56 / night

$390 - $668 / week

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from $56 / night

(1) Excellent 

24

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 $45 / night

$315 - $561 / week

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from $45 / night

(2) Excellent 

12

Porto Santo Stefano Vacation penthouse rental

Monte Argentario / Porto Santo Stefano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Wonderful Penthouse in Porto Santo Stefano, great Sea view and very big terrace with all comforts. The apartment is fully equipped, AC, dishwasher, washing machine. It is in a 5 minute walk to the center of the town, it is well served for grocery's. Full View from Port …see more

from $118 / night

$825 / week

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from $118 / night

15

B&b rental in Follonica

Province of Grosseto / Follonica

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 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 $73 / night

$449 - $786 / week

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from $73 / night

5

Massa Marittima Vacation farmhouse rental

Province of Grosseto / Massa Marittima

2 9 1 night min

  • 2 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
The farm is located on the top of a hill, facing the sea, dipped in the green of the Mediterranean scrub, among woods of holm oaks and olive trees the property where guests can quietly stroll. You reach the village of Tatti, an enchanting medieval village, located in t …see more

from $202 / night

$561 / week

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from $202 / night

(14) Excellent 

22

Cala Piccola Vacation apartment rental

Monte Argentario / Cala Piccola

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Dear Guests We are pleased to present this very beautiful villa located on the most extreme point of the Argentario coast, perched on top of a rocky cliff that drops straight down into the sea and offers a breathtaking view. The position of this beach villa makes it un …see more

from $303 / night

$1234 - $2973 / week

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from $303 / night

(1) Excellent 

11

Vacation apartment in Montieri

Province of Grosseto / Montieri

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 40 mi
  • Child friendly
'Il Castagneto' apartment is the smaller of the two apartments in the Villa of Borgo al Fango. It komuniziert with a panoramic terrace with the larger apartment 'Il Ribocciolo'. A double bedroom with extra bed is located on the first floor along with the bad. The bathr …see more

from $79 / night

$382 - $1066 / week

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from $79 / night

(1) Very Good 

27

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 $56 / night

$290 - $479 / week

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from $56 / night

(5) Very Good 

86

Vacation apartment rental

Province of Grosseto / Follonica

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Tuscany style, recently reconditioned COUNTRY HOUSE, very close to the SEA SIDE, with a astonishing view of the Follonica Gulf, in front to ISOLA ELBA.This villa is made of 4 appartaments. Each is formed by 1 large LIVING and DINING room (that has a Bed-Sofa), 2 l …see more

from $57 / night

$371 - $1571 / week

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from $57 / 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 $57 / night

$303 - $898 / week

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from $57 / night

69

Vacation villa with golf nearby in Punta Ala

Castiglione Della Pescaia / Punta Ala

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Wonderful and panoramic villa in front of Punta Ala sea, close to Castiglione della Pescaia town, with luxurious living room (70 mq), four bedrooms, three bathrooms, wide fitted outdoor rooms, garden, outdoor hot/cold shower, parking, washing machine, dishwasher, dry …see more

from $191 / night

$1336 - $3562 / week

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from $191 / night

33

Civitella Paganico Vacation cottage rental

Province of Grosseto / Civitella Paganico

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The Villa t is located in an historic former church It has a surface of 220m and it's furnished for 8-10 persons. Four bedrooms, two bathroom, two kitchen with a large dining-room, a living room with a wood stove, which makes your evenings warmer. There are variou …see more

from $304 / night

$2132 - $2805 / week

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from $304 / night

22

Vacation farmhouse with swimming pool in Montemassi

Province of Grosseto / Montemassi

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Swimming pool
Welcome to Agriturismo Pereti and the Rocca appartment. The Rocca apartment is has an independent entrance, private terrace, private bathroom, WiFi, and it enjoys beautiful tranquil views at the surrounding hills and the medieval village of Roccatederighi. The apartmen …see more

from $84 / night

$557 / week

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from $84 / night

(2) Very Good 

22

Vacation farmhouse with swimming pool in Arcidosso

Province of Grosseto / Arcidosso

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Green Mountain farmhouse with large fenced garden pool Court pleasantly flowered. possible excursions around the apartment consists of three bedrooms two double beds and one with a double bed and a Castle-two bathrooms kitchen lounge dining room with pool and great dini …see more

from $169 / night

$1177 / week

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from $169 / night

1