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

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Castiglione Della Pescaia
246 properties
Orbetello
157 properties
Grosseto
154 properties
Scarlino
131 properties
Manciano
118 properties
Monte Argentario
114 properties
Sorano
80 properties
Massa Marittima
80 properties
Follonica
77 properties
Pitigliano
58 properties
Civitella Paganico
56 properties
Capalbio
53 properties
Roccastrada
51 properties
Magliano in Toscana
43 properties
Seggiano
39 properties
Scansano
39 properties
Gavorrano
29 properties
Braccagni
27 properties
Castel Del Piano
26 properties
Roccatederighi
25 properties

Province of Grosseto

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1,905 Vacation rentals

(2) Excellent 

40

Vacation hotel apartment in Puntone

Scarlino / Puntone

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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

$391 / week

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from $93 / night

7

Vacation villa in Manciano

Province of Grosseto / Manciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 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 $204 / night

$1,162 / week

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from $204 / 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 $83 / night

$581 - $2,671 / week

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from $83 / night

(1) Excellent 

26

Vacation hotel apartment in Punta Ala

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Rent weekly or for longer periods an apartment in Punta Ala, a town to the port, for the summer and autumn 2018. The apartment has two rooms with 5 beds, consisting of a living room with 3 beds (2 sofa beds) , main bathroom, kitchen, master bedroom with terrace and en s …see more

from $67 / night

$465 - $1,220 / week

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Responds fast!
avg. 3 hours 31 minutes

from $67 / 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 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 $83 / night

$581 - $2,671 / week

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from $83 / night

19

Vacation home in Punta Ala

Castiglione Della Pescaia / Punta Ala

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

$1,162 - $2,613 / week

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from $166 / night

11

Vacation apartment in Manciano

Province of Grosseto / Manciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
Spacious farmhouse in Tuscany-Room 2 Manciano, Tuscany, Italy 1 bedroom 1 bed Our house, 15 minutes from Terme di Saturnia, and 'ideal for those who want to enjoy a relaxing and comfortable holiday in Tuscany. With 2 large rooms available for 2 people, we can accommodat …see more

from $76 / night

$465 / week

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from $76 / night

(6) Very Good 

14

Vacation condo 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
It's a good apartment, recently renovated, consists of a bedroom, children's bedroom, living room with kitchen wall, bathroom with shower and spacious terrace. The apartment is located in a five-storey building surrounded by greenery of the pinewood and only 150 metres …see more

from $58 / night

$407 - $1,150 / week

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from $58 / night

(4) Very Good 

Certificate of Excellence

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 wonderful Terme di Saturnia and a few hundred meters from the Mill Falls. Living room with fireplace and fully equipped kitchenette, TV and a comfortable sofa bed for one person, d …see more

Certificate of Excellence

from $93 / night

$523 - $639 / week

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Responds fast!
avg. 2 hours 9 minutes

from $93 / night

12

Farmhouse rental in Grosseto with shared pool, golf nearby

Province of Grosseto / Grosseto

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly
Family-run it located on a slight hill and surrounded by an olive grove on the edge of the Maremma Natural Park Here you will be guests in apartments equipped with all comforts to spend pleasant days between sea, sports, nature, culture and healthy eating organic farm i …see more

from $105 / night

$732 / week

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from $105 / night

12

Vacation finca rental

Province of Grosseto / Sorano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
This historic home was a Customs House in the 17th century where those who crossed the border between the Papal State and the Grand Duchy of Tuscany, stopped in search of refreshment.Sant'Egle therefore has remained so- a place to rest, seek refreshment, meet friends, a …see more

from $151 / night

$1,045 / week

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from $151 / night

(3) Excellent 

24

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
Il Gabbiano is a cool and comfortable accommodation to the first floor of a terraced two-storey 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 dine …see more

from $47 / night

$291 - $1,324 / week

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Responds fast!
avg. 33 minutes

from $47 / night

(3) Very Good 

18

Giannella Vacation home rental

Orbetello / Giannella

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Raffinato mini casale immerso negli ulivi appena ristrutturato e rifinito con pavimenti in cotto antico e sofitti con travi di legno. Composto da ampio soggiorno con letto matrimoniale, divano, TV grande shermo piatto, armadio guardaroba e camino, un ampio bagno con …see more

from $116 / night

$615 - $928 / week

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from $116 / night

(7) Excellent 

16

Castiglione Della Pescaia Vacation apartment rental

Province of Grosseto / Castiglione Della Pescaia

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.6 mi
  • Child friendly
  • Pet friendly
Appartamento in affitto a Castiglione della Pescaia,Grosseto, Toscana Piano terra, senza scalini a 5 minuti a piedi dalla piazza centrale e a 7 minuti a piedi dal mare e dal Porto. Terrazza esterna privata grande e abitabile con tavolo rotondo, sedie, salottino da est …see more

from $142 / night

$706 - $1,212 / week

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from $142 / night

(3) Very Good 

10

Scarlino Scalo Vacation apartment rental

Scarlino / Scarlino Scalo

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $58 / night

$407 - $697 / week

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from $58 / night

(1) Very Good 

26

Vacation home in Monte Argentario

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
Sea Sun is in a small rented villa on the promontory of Monte Argentario, 7 km from the town of Porto Santo Stefano and has a beautiful view of the coast and the Tuscan archipelago. It has many very panoramic private green spaces and equipped with deckchairs, sun beds a …see more

from $82 / night

$522 - $1,102 / week

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Responds fast!
avg. 1 hour 18 minutes

from $82 / 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 $58 / night

$279 - $523 / week

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from $58 / night

(5) 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
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
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 $47 / night

$326 - $1,045 / week

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from $47 / night

(1) Very Good 

22

Vacation apartment in Porto Ercole

Monte Argentario / Porto Ercole

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • 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 $99 / night

$691 / week

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from $99 / night

(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 $107 / night

$664 - $1,593 / week

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from $107 / 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 $93 / night

$652 - $948 / week

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from $93 / night

(3) Very Good 

18

Vacation home in Tirli

Castiglione Della Pescaia / Tirli

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Old house in the village of Tirli, comfortably accommodates 8 people. On the ground floor there is a spacious living room with fireplace and kitchenette. Upstairs, as well as a breathtaking, there are 4 bedrooms and two bathrooms (one with shower and one with bathtub). …see more

from $67 / night

$464 - $754 / week

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Responds fast!
avg. 1 hour 56 minutes

from $67 / night

32

Porto Santo Stefano Vacation villa rental

Monte Argentario / Porto Santo Stefano

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Villa Fiorita is a marvelous farmhouse in front of the Isola del Giglio. It enjoys a beautiful view across the Tuscan Archipelago. Inside the park of the Villa, there is a pool of 10x5 meters, a space with basketball hoop, a bowling green lawn is a set up with play faci …see more

from $407 / night

$2,845 / week

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Responds fast!
avg. 3 hours 26 minutes

from $407 / 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 $57 / night

$399 / week

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from $57 / night

21

Apartment rental in Punta Ala with shared pool, golf nearby

Castiglione Della Pescaia / Punta Ala

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
ELEGANT APARTMENT IN AN EXCLUSIVE RESIDENCE IN PUNTA ALA, TUSCANY IN THE HILL SURROUNDED BY GREEN MEDITERRANEAN VEGETATION WITH VIEWS OVER THE ISLAND OF ELBA, DOMINATING THE SEA WITH LARGE PARK AND POOL.BORDERING ONE OF THE BEST GOLF COURSES IN EUROPE. CHANCE SAILING, H …see more

from $150 / night

$1,045 - $1,452 / week

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Responds fast!
avg. 3 hours 16 minutes

from $150 / night

4

Vacation farmhouse in Alberese

Province of Grosseto / Alberese

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
A wonderful pizza in the heart of Maremma …see more

from $70 / night

$488 / week

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from $70 / night

21

Grosseto Vacation townhouse rental

Province of Grosseto / Grosseto

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
In Upper Maremma, in the municipality of Roccastrada on the border of the provinces of Siena and Grosseto through woods and forests is Torniella a small medieval town was born around the year 1000. In the fortress of the village is the castle that belonged to Ardenghesc …see more

from $209 / night

$1,452 / week

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from $209 / 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 $47 / night

$326 / week

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from $47 / 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 $209 / night

$581 / week

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from $209 / night

9

Vacation home accommodation

Capalbio / Capalbio Scalo

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Private garden
The house (60 sqm) is part of an old barn and is located in the countryside 1 km from Capalbio airport. The house comprises: living room with a stove / old fireplace, a master bedroom, a double bedroom on a mezzanine, 2 bathrooms, kitchen, furnished veranda. The small g …see more

from $87 / night

$465 / week

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from $87 / night

17

Vacation home in Porto Santo Stefano

Monte Argentario / Porto Santo Stefano

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Small and cozy house with garden in a very quiet area. To reach the house you must get an amount equal to 3 floors of stairs, so it is not recommended for people who move with difficulty. The house has a living area of 56m ² + terrace of 20 sqm + 1000 sqm approx …see more

from $117 / night

$813 / week

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from $117 / night

15

Penthouse rental in Montiano

Magliano in Toscana / Montiano

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Cozy and spacious attic, three comfortable bedrooms, two bathrooms, one with bathtub and one with shower, large fireplace in the living room comfortable even for cooking. Bright with skylights in the ceiling and with views from Windows that ranges from hills to the sea. …see more

from $82 / night

$697 - $1,104 / week

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from $82 / night

26

Vacation farmhouse in Ampio

Castiglione Della Pescaia / Ampio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Pet friendly
The farm is divided into 2 independent apartments. Each apartment has a kitchen with living room, two double bedrooms and a bathroom. Also it has a veranda overlooking the garden where you can eat. We are just 7 km from the sea and from the town center, a short walk fro …see more

from $70 / night

$720 - $848 / week

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Responds fast!
avg. 2 hours 26 minutes

from $70 / 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 $326 / night

$2,090 - $3,716 / week

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from $326 / 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

$407 - $465 / week

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Responds fast!
avg. 1 hour 15 minutes

from $68 / night

21

Scansano Vacation apartment rental

Province of Grosseto / Scansano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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

$488 - $1,463 / week

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Responds fast!
avg. 1 hour 28 minutes

from $70 / 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 $70 / night

$407 - $697 / week

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Responds fast!
avg. 3 hours 26 minutes

from $70 / night

18

Vacation farmhouse in Semproniano

Province of Grosseto / Semproniano

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
L 'Farm Radicino The Source is a cottage which is located 3km from the town of Semproniano. Located on top of a hill is set in an extremely quiet environment, submerged by the green surrounding nature, fruit trees, olive trees and oaks. It enjoys stunning views of the M …see more

from $93 / night

$651 / week

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from $93 / 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 $67 / night

$459 / week

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from $67 / 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 $76 / night

$465 - $813 / week

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from $76 / night