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

Close

View larger map

Also consider

Castiglione Della Pescaia
255 properties
Orbetello
148 properties
Grosseto
130 properties
Manciano
113 properties
Sorano
87 properties
Capalbio
71 properties
Scarlino
71 properties
Porto Santo Stefano
68 properties
Massa Marittima
59 properties
Pitigliano
55 properties
Follonica
46 properties
Porto Ercole
44 properties
Roccastrada
42 properties
Monte Argentario
41 properties
Civitella Paganico
38 properties
Magliano in Toscana
34 properties
Scansano
31 properties
Seggiano
30 properties
Gavorrano
26 properties
Arcidosso
24 properties

Province of Grosseto

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,671 Vacation rentals

(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

$481 - $2456 / week

Book View

from $69 / night

(4) Very Good 

19

Vacation home in Castiglione Della Pescaia

Province of Grosseto / Castiglione Della Pescaia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Nice and quite apartment 75sqm , delightful outside terrace with splendid view on Orbetello lagoon and Giglio island. Car parking with sun shield. Two bedrooms, one with queen size bed and one with 2 single beds, shower/WC, kitchen and large living-room, Digital LCD TV.  …see more

from $77 / night

$534 / week

Inquire View

from $77 / night

(2) 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 very last o  …see more

from $266 / night

$1708 - $2243 / week

Book View

from $266 / night

Featured properties

22

Castiglioncello Bandini Vacation villa rental

Province of Grosseto / Castiglioncello Bandini

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
As you enter the driveway at Fonte Al Canale your eye is drawn to a row of wind chimes, the work of internationally renowned sculptor, Bruno Gasser. Fonte Al Canale is a beautifully restored Villa, set high upon a Tuscan hill, with a magnificent view of the valley belo  …see more

from $351 / night

$2456 - $3738 / week

Book View

from $351 / 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 $374 / night

$1923 - $3311 / week

Book View

from $374 / night

5

Province of Grosseto / Grosseto

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation

 …see more

from $54 / night

$374 / week

Book View

from $54 / night

(1) Excellent 

33

Vacation villa with shared pool in Triana, Italy

Roccalbegna / Triana, Italy

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 67 mi
  • Swimming pool
  • Child friendly
The property with two bedrooms is on the first floor of an ancient cottage recently restored. It is nestled in the hillside with spectacular views across the valley and down to the coast. In clear days you can see the Giglio island. It has its own private garden where y  …see more

from $86 / night

$598 - $849 / week

Book View

from $86 / 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 $54 / night

$374 / week

Book View

from $54 / 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

$588 - $812 / week

Book View

from $91 / night

(1) Very Good 

9

Province of Grosseto / Civitella Paganico

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly

 …see more

from $50 / night

$344 / week

Book View

from $50 / night

18

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

 …see more

from $54 / night

$428 - $748 / week

Book View

from $54 / 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 $65 / night

$449 / week

Book View

from $65 / 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

$235 / week

Book View

from $38 / night

(1) Excellent 

15

Province of Grosseto / Roccatederighi

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from $107 / night

$641 / week

Book View

from $107 / night

(1) Excellent 

24

Vacation apartment in Castiglione Della Pescaia

Province of Grosseto / Castiglione Della Pescaia

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Prestigious apartment with panoramic views and private balcony situated in the medieval village of Castiglione di Pescaia, in Via Amore. The property has been restored leaving unchanged the characteristic features and the classic Tuscan style ceilings and furnishings.  …see more

from $198 / night

$1228 - $3183 / week

Book View

from $198 / night

(29) Excellent 

29

Vacation b&b in Vetulonia

Province of Grosseto / Vetulonia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Air conditioning
Il Mandorlo is the bed and breakfast of the farm LE GUAZZE BONE. It is an independent, romantic small house for two people, converted from a farm house, fully restored: a piece of paradise set in a landscape that looks like a painting. An enchanted place among the green  …see more

from $70 / night

$486 - $636 / week

Book View

from $70 / night

(3) Excellent 

24

Isola Del Giglio / Giglio Castello

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from $107 / night

$695 - $1127 / week

Book View

from $107 / night

21

Province of Grosseto / Scansano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from $54 / night

$374 - $1431 / week

Book View

from $54 / night

(1) Very Good 

21

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

 …see more

from $49 / night

$262 / week

Book View

from $49 / night

(5) Very Good 

14

Province of Grosseto / Principina a Mare

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $54 / night

$358 - $1047 / week

Book View

from $54 / night

31

Talamone Vacation villa rental

Orbetello / Talamone

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Orizzonte is an absolutely imposing villa located in Tuscany, in an impressively unique position on a cape extending into the Tyrrhenian sea. This formerly watchtower belonging to the year 1000 has been carefully preserved and it maintains untouched all its ancien  …see more

from $1068 / night

$7475 - $15484 / week

Inquire View

from $1068 / night

(4) Excellent 

14

Province of Grosseto / Principina a Mare

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from $54 / night

$374 / week

Book View

from $54 / night

(5) Excellent 

13

Province of Grosseto / Vetulonia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly

 …see more

from $49 / night

$353 / week

Book View

from $49 / night

28

Vacation villa in Porto Santo Stefano

Province of Grosseto / Porto Santo Stefano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Gorgeous and exclusive apartment in a villa of 100sqm with garden. It is located in the famous Argentario and it is about 300 meters far from one of the most beautiful beach of Tuscany.The apartment is located 1 km far from Porto Santo Stefano in Pozzarello area. Du  …see more

from $11 / night

$75 / week

Book View

from $11 / night

24

Vacation villa in Porto Ercole

Province of Grosseto / 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 $460 / night

$3215 - $8522 / week

Book View

from $460 / night

(2) Very Good 

20

Province of Grosseto / Castiglione Della Pescaia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $47 / night

$278 - $1159 / week

Book View

from $47 / 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

$641 - $1608 / week

Book View

from $92 / night

(1) Excellent 

13

Castiglione Della Pescaia / Punta Ala

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $43 / night

$299 - $1282 / week

Book View

from $43 / night

(5) Very Good 

13

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+

 …see more

from $54 / night

$374 / week

Book View

from $54 / 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 $54 / night

$374 - $481 / week

Book View

from $54 / night

14

Grosseto / Bagno Roselle

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $65 / night

$428 / week

Book View

from $65 / night

41

Villa rental in Rispescia with swimming pool

Grosseto / Rispescia

6 18 7 nights min

  • 6 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Vigna Maremmana – Rispescia – Tuscany Coast<br>6 Bedrooms (3 double, 3 Suites) – Pool<br>Country charm in a Tuscan home on the range overlooking luscious vineyards. Maremma is renown as the land of the Tuscan cowboy featuring a wonderful Natu  …see more

from $458 / night

$3204 - $3951 / week

Book View

from $458 / night

(1) Very Good 

12

Scansano Vacation cottage rental

Province of Grosseto / Scansano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Pet friendly
The cottage is located close to the ancient Etruscan village of Scansano in the Tuscan Maremma and is surrounded by olive groves. The setting is perfect for those wishing to combine the tranquility of the countryside with the proximity to ancient villages and exploratio  …see more

from $97 / night

$641 - $1495 / week

Book View

from $97 / night

(2) Excellent 

27

Sorano / San Quirico

2 10 2 nights min

  • 2 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 10 mi
  • Child friendly
  • Ask about pets

 …see more

from $97 / night

$673 - $972 / week

Book View

from $97 / night

(1) Excellent 

40

Vacation villa with swimming pool in Capalbio

Province of Grosseto / Capalbio

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
This fabulous recently renovated 4 BR - 4 ½ BA villa sits on the grounds of a wonderful historic estate, just minutes away from the town of Capalbio and the beautiful sandy beaches of Maremma, Tuscany’s Southern coast. Featuring more than 3800 s.f. (350 s.m.) of inn  …see more

from $374 / night

$2617 / week

Book View

from $374 / night

24

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
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

$481 - $2456 / week

Book View

from $69 / night

(1) Excellent 

17

Province of Grosseto / Ravi

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from $43 / night

$267 / week

Book View

from $43 / night

(1) Excellent 

14

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

 …see more

from $65 / night

$748 / week

Book View

from $65 / night

(1) Excellent 

10

Province of Grosseto / Giannutri Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $115 / night

$801 / week

Book View

from $115 / 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

$588 - $1132 / week

Book View

from $84 / night