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

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Castiglione Della Pescaia
249 properties
Orbetello
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Manciano
116 properties
Sorano
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Scarlino
85 properties
Massa Marittima
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Capalbio
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Follonica
60 properties
Pitigliano
56 properties
Roccastrada
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Civitella Paganico
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Magliano in Toscana
35 properties
Gavorrano
33 properties
Scansano
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Seggiano
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Arcidosso
22 properties
Semproniano
21 properties
Castel Del Piano
21 properties

Province of Grosseto

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1,667 Vacation rentals

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(3) Very Good 

20

Province of Grosseto / Grosseto

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

 …see more

from $30 / night

$191 / week

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from $30 / 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 $43 / night

$297 - $530 / week

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from $43 / night

(40) Excellent 

24

Farmhouse rental in Gavorrano with swimming pool, golf nearby

Province of Grosseto / Gavorrano

3 33 1 night min

  • 3 bedrooms
  • Sleeps 33
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
"Casa Conti di Sotto", is a small ,private,rural house with 7 independents houses, renovated in 2015 between the green Mediterranean maquis and marvellous undulating landscape at only 10 minutes from the best beaches and reef of Tuscany, just in front of Elb  …see more

from $61 / night

$423 - $1061 / week

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from $61 / night

(1) Excellent 

40

Scarlino / Puntone

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $85 / night

$356 - $1424 / week

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from $85 / night

(4) Excellent 

19

Province of Grosseto / Sticciano Scalo

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Child friendly

 …see more

from $53 / night

$371 - $477 / week

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from $53 / 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 $424 / night

$2967 - $7416 / week

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from $424 / night

22

Province of Grosseto / Castiglione Della Pescaia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from $84 / night

$583 - $1123 / week

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from $84 / night

(1) Excellent 

15

Manciano / Saturnia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 35 mi
  • Ask about children
  • Pet friendly

 …see more

from $53 / night

$371 - $689 / week

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from $53 / night

33

Vacation home with shared pool in Cala Piccola

Monte Argentario / Cala Piccola

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
IN THE RENTAL PRICE IT IS ALWAYS INCLUDED: * the entrance of the private beach/establishmen with your own space with use of one sun umbrela and sun chairs. Bar and fish restaurant. small play ground for children * Use of the swimming pool close by the house (+-70 metres  …see more

from $91 / night

$636 - $2331 / week

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from $91 / night

6

Province of Grosseto / Santa Fiora

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden

 …see more

from $27 / night

$212 - $318 / week

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from $27 / night

(3) Excellent 

6

Manciano / Saturnia

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from $91 / night

$583 - $806 / week

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from $91 / night

35

Province of Grosseto / Gavorrano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning

 …see more

from $43 / night

$297 / week

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from $43 / night

(1) Excellent 

24

Vacation apartment in Monte Argentario

Province of Grosseto / Monte Argentario

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This stunning, brand new apartment is just 6 metres from the sea, inside an old Tuscan Villa, located in a tiny, wonderful rocky bay called "Le Cannelle". It is as if you were on a boat: you can be the very first one to swim in the sea in the morning, or the v  …see more

from $264 / night

$1694 - $2225 / week

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from $264 / 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 $38 / night

$234 / week

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from $38 / night

(26) 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 $265 / night

$1907 - $3284 / week

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from $265 / night

(3) Very Good 

30

Home rental in Ansedonia with shared pool

Orbetello / Ansedonia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Stella di Mare has a large comfortable terrace with a full sea view perfect for relaxing and outdoor dining. It is 500m from the glorious sandy expanse of the 7km long Feniglia beach and pine forest reserve. A free minibus takes people down to the beach every hour  …see more

from $92 / night

$636 - $1595 / week

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from $92 / 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  …see more

from $338 / night

$2363 - $5475 / week

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from $338 / night

(1) Very Good 

10

Manciano / Saturnia

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $91 / night

$530 / week

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from $91 / night

16

Vacation home with swimming pool in Isola Del Giglio

Province of Grosseto / Isola Del Giglio

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Top location ISOLA DEL GIGLIO in TUSCANY (GIGLIO ISLAND) , 143 km from Rome international airport and 190 km from Florence airport, 200 km from Pisa airport and 12 sea miles from the Silver Coast (Porto Santo Stefano ) , a 50 minute sea crossing with the frequent car f  …see more

from $159 / night

$1060 / week

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from $159 / night

(4) Excellent 

12

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

 …see more

from $53 / night

$371 - $594 / week

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from $53 / night

21

Province of Grosseto / Monte Argentario

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Ask about children
  • Ask about pets

 …see more

from $53 / night

$371 - $583 / week

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from $53 / night

16

Vacation villa with swimming pool in Porto Santo Stefano

Monte Argentario / Porto Santo Stefano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa was originally built as a countryside house, expanded during the decades, and finally refurbished to offer all amenities. The house offers four bedrooms, two full bathrooms and a separate toilet. It has also a spacious kitchen and a very large living and dinin  …see more

from $152 / night

$1060 - $2649 / week

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from $152 / night

9

Grosseto / Rispescia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly

 …see more

from $64 / night

$445 / week

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from $64 / night

26

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

 …see more

from $52 / night

$361 - $1007 / week

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from $52 / night

(15) Very Good 

26

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
Bilocale a Punta Ala, con una camera matrimoniale con soggiorno con divano letto, angolo cottura bagno e antibagno. Posto auto, Aria condizionata. Biancheria per letti e bagno. Rta a Punta Ala immersa nel parco a 800 metri dallo stabilimento balneare, servizio navetta o  …see more

from $69 / night

$477 - $2437 / week

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from $69 / night

26

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

 …see more

from $75 / night

$424 - $636 / week

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from $75 / night

(1) Very Good 

28

Province of Grosseto / Arcidosso

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Ask about pets

 …see more

from $53 / night

$350 / week

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from $53 / night

(1) Excellent 

10

Scarlino / Scarlino Scalo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $53 / night

$371 - $636 / week

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from $53 / night

(1) Excellent 

8

Province of Grosseto / Santa Fiora

2 4 2 nights min

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

 …see more

from $53 / night

$371 / week

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from $53 / night

(1) Excellent 

26

Province of Grosseto / Magliano in Toscana

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

 …see more

from $212 / night

$1589 - $2013 / week

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from $212 / night

(1) Excellent 

18

Orbetello / Giannella

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $106 / night

$562 - $954 / week

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from $106 / night

60

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 $182 / night

$1272 - $3390 / week

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from $182 / night

(2) Very Good 

12

Sassofortino Vacation farmhouse rental

Province of Grosseto / Sassofortino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
Casa Lisa is only 10 minutes walk from the Tuscan village of Sassofortino famous for its chestnut forests and castle. Set in the hills above the plains of the Maremma with lovely views towards the sea and island of Elba. A recently restored Italian farmhouse set in its  …see more

from $133 / night

$933 - $1763 / week

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from $133 / night

(3) Excellent 

23

Monte Argentario / Cala Piccola

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $99 / night

$689 - $2437 / week

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from $99 / night

23

Apartment rental in Ansedonia with golf nearby

Orbetello / Ansedonia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Our apartment is located in the heart of the pretty village of Orbetello, placed between the enchanting blue of the Tyrrhenian Sea, the harmony of the Laguna and the peace of the green of Monte Argentario. The cosy little building that houses the apartment is located in  …see more

from $80 / night

$557 / week

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from $80 / night

19

Castiglione Della Pescaia / Punta Ala

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $152 / night

$1060 - $2384 / week

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from $152 / night

100

Vacation villa with swimming pool in Grosseto

Province of Grosseto / Grosseto

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
ExteriorsGrosseto is located in the southern part of Tuscany, and it is the perfect place for exploring some Roman and Etruscan finds and archaeological sites, as well as for tasting some delicious recipes and the finest local wines.From the south of the region, visitor  …see more

from $477 / night

$3178 - $5191 / week

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from $477 / night

26

Massa Marittima Vacation farmhouse rental

Province of Grosseto / Massa Marittima

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Farmhouse "Il Fico" is an old farmhouse on two floors recently renovated to offer the best comfort during your stay. Is it possible to accommodate 11 persons, belonging to a single group. On the ground floor there is the large kitchen with fireplace, a bathroo  …see more

from $117 / night

$774 - $848 / week

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from $117 / night

5

Province of Grosseto / Principina a Mare

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $64 / night

$318 / week

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from $64 / night

15

Province of Grosseto / Monte Argentario

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $181 / night

$1261 / week

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from $181 / night