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Grosseto Vacation Rentals

Hotels (22)

B&Bs / Inns (8)

Specialty Lodging (11)

Vacation Rentals (45)

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Podere Ulivo della Strega - Merlino, Magliano in Toscana
Podere Ulivo della Strega - Merlino
    Price: €2,537 - €4,001/week
  • Bedrooms: 4, sleeps 7
  • Bathrooms: 3
    • Contact Manager
Podere Ulivo della Strega - Margot, Magliano in Toscana
Podere Ulivo della Strega - Margot
    Price: €2,537 - €4,001/week
  • Bedrooms: 4, sleeps 9
  • Bathrooms: 2
    • Contact Manager
Fontedelsalcio Trenta Vizi 34352002, Cinigiano
Fontedelsalcio Trenta Vizi 34352002
    Price: Inquire for rates
  • Bedrooms: 2, sleeps 7
  • Bathrooms: 1
    • Contact Manager
Montorsi Montorsi - 805.1 16524001, Roccastrada
Montorsi Montorsi - 805.1 16524001
    Price: Inquire for rates
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
  • Min stay: 7
    • Contact Manager
Casa montecalvo Casa Montecalvo - 830.1 16527001, Roccastrada
Casa montecalvo Casa Montecalvo - 830.1 16527001
    Price: Inquire for rates
  • Bedrooms: 1, sleeps 3
  • Bathrooms: 1
  • Min stay: 7
    • Contact Manager
La fornace di roccastrada La Fornace di Roccastrada - 800.1 16523001, Roccastrada
La fornace di roccastrada La Fornace di Roccastrada - 800.1 16523001
    Price: Inquire for rates
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
  • Min stay: 7
    • Contact Manager
Pietreto Pietreto - 810.1 16525001, Roccastrada
Pietreto Pietreto - 810.1 16525001
    Price: Inquire for rates
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
  • Min stay: 7
    • Contact Manager
Casale fonte Casale Fonte - 811.1 16526001, Roccastrada
Casale fonte Casale Fonte - 811.1 16526001
    Price: Inquire for rates
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 1
  • Min stay: 7
    • Contact Manager
Punta ala 200.3 46783003, Punta Ala
Punta ala 200.3 46783003
    Price: Inquire for rates
  • Bedrooms: 2, sleeps 4
    • Contact Manager
La colombaia La Colombaia - 800.1 16515001, Massa Marittima
La colombaia La Colombaia - 800.1 16515001
    Price: Inquire for rates
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
  • Min stay: 7
    • Contact Manager

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Il Salottino, Grosseto
Il Salottino
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 9
Whether you love the beach or the hills, the museums or the vineyards, this Tuscany villa near Montiano is the one for you! Spend days relaxing at the nearby ...
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    €2,754 - €3,845
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Azienda agricola la casetta Azienda Agricola La Casetta - 860.1 16564001, Grosseto
Azienda agricola la casetta Azienda Agricola La Casetta - 860.1 16564001
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 3, sleeps 6
Bathrooms: 2
Min stay:7
"Il Cipresso", 5-room semi-detached house 100 m2 on 2 levels, on the ground floor, fully renovated, tasteful furnishings: 2 double bedrooms. Living/dining ...
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La Vigna, Grosseto
La Vigna
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 6, sleeps 12
“Villa La Vigna” is a luxury mansion set in its own oasis in the heart of southern Tuscany, about 40 minutes drive from Siena and a twenty-five minute drive ...
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The following rentals are within 25 miles of Grosseto, Tuscany.

Stunning villa, sea views, private pool, Porto Santo Stefano
Stunning villa, sea views, private pool
Contact Owner
4 of 5 stars 1 review
Management: Verified owner
Property: Villa
Bedrooms: 5, sleeps 11
Bathrooms: 4
Min stay:7
Tuscan Villa sleeps 10 (3 double bedrooms, 2 twin bedrooms) swimming pool, large garden and parking area with stunning views over the Tuscan archipelago. ...
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    €2,546 - €4,895
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Apparita, Paganico
Apparita
Contact Manager
3.5 of 5 stars 5 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
Beautiful farmhouse that has been carefully restored [350 m2] set in the verdant hills of the Maremma area. The house is in a portion of a classical and ...
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    €879 - €2,045
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Villa Fabiana, Campagnatico
Villa Fabiana
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 9
Bathrooms: 3
With surrounding vineyards and olive trees as well as 360-degree views of the countryside, it's hard not to be immediately charmed by this holiday ...
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    €1,644 - €3,868
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Podere Ulivo della Strega, Magliano in Toscana
Podere Ulivo della Strega
Contact Manager
Nightly rate from
€1,416
Management: Professional
Property: Rental Home
Bedrooms: 8, sleeps 16
Bathrooms: 5
This exquisite farmhouse in Tuscany certainly is the place for two families traveling together! Whether or not you turn right or left when entering the villa, ...
  • Nightly
    €1,416
  • Weekly
    €3,904 - €5,953
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La Faticosa, Porto Santo Stefano
La Faticosa
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Charming small independent villa [85 m2] which has been recently restored situated near the sea-side, inside the residential complex of Cala Piccola. The ...
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    €1,438 - €2,950
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Rocco sul Tirreno, Talamone
Rocco sul Tirreno
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 4
Treat yourself to a unique experience while vacationing on the Italian coast in an ancient castle! Reside where you can see and smell the ocean from any ...
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    €8,262 - €10,393
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Maremma, Castiglione Della Pescaia
Maremma
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
Apartment [120 m2] in a two-family villa that is occasionally inhabited by the owner at Principina Mare [grocery shops, horse riding, swimming pool, tennis], ...
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    €967 - €1,886
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Casa del Podesta Il Podesta 43110002, Civitella Paganico
Casa del Podesta Il Podesta 43110002
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 2, sleeps 4
Bathrooms: 1
Il Podesta is a two-bedroom apartment on the ground floor of a beautiful stone house in a small medieval village. It has recently been restored to reveal ...
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Albinia 900.1 46382001, Albinia
Albinia 900.1 46382001
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 4, sleeps 8
Min stay:7
6-room apartment 200 m2, on the ground floor, comfortable, nice, modern and spacious furnishings: large living/dining room with open fireplace, TV, CD-player ...
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Podere san lorenzo Podere San Lorenzo - 600.1 30448001, Cinigiano
Podere san lorenzo Podere San Lorenzo - 600.1 30448001
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 1, sleeps 3
Min stay:7
"Podere San Lorenzo", 2-room apartment 50 m2, on the ground floor, very simple furnishings: living/dining room with 1 sofa bed. 1 double bedroom, exit to the ...
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Roccastrada 812.1 42848001, Roccastrada
Roccastrada 812.1 42848001
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 1, sleeps 2
Min stay:7
"Casale Belvedere", 1-room house 33 m2, on the ground floor, fully, comfortable furnishings: open living room with 1 double bed, shower/bidet/WC, ...
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Poggetti santa rosa Poggetti Santa Rosa - 820.1 16548001, Scarlino
Poggetti santa rosa Poggetti Santa Rosa - 820.1 16548001
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 3, sleeps 6
Bathrooms: 2
Min stay:7
5-room apartment 140 m2, on the ground floor: large living/dining room with open fireplace and TV. 1 double bedroom. 2 rooms, each room with 2 beds. ...
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Roccatederighi, Roccatederighi
Roccatederighi
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 1, sleeps 4
This charming house, the tower of the XII century fortress of nearby Roccatederighi, has been restored with the same exquisite artistry as the houses at Pieve ...
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    €1,344 - €1,740
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The Lookout Tower, Castiglione Della Pescaia
The Lookout Tower
Contact Manager
Management: Professional
Property: Villa
Bedrooms: 1, sleeps 4
Centuries ago a lookout tower and garrison for soldiers with an eye out for Barbaresque pirates, this panoramically placed complex has recently become a ...
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    €2,672 - €4,007
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Itaca, Massa Marittima
Itaca
Contact Manager
Management: Professional
Property: Rental Home
Sleeps: 2
This apartment "Itaca", 85 m2, is spread over 2 levels. The interior of the accommodation can differ slightly from the pictures. However, the level of comfort ...
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    €305 - €592
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Residence Sole Maremma, Castiglione Della Pescaia
Residence Sole Maremma
Contact Manager
Management: Professional
Property: Condo/Apartment
Sleeps: 2
Residence Sole Maremma is hidden away in the green surroundings with a central facilities centre in the complex, your children will not be missing anything. ...
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    €376
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Grosseto Vacation Rental Advice
sand beach
Posted by NorthernCindy, Aug 19, 2009
... t get away from crowds at all. This is a family trip (boys ages 12 and 15) so we're not looking for night life. We'll look for an apartment, vacation rental, or resort that offers self-catering to stay. We desperately need some good advice! Thanks so much ... more
Holiday in Gavorrano
Posted by RooneyUK, Aug 24, 2007
I'm sorry I don't know. We own a 2 bedroom apartment but as there is just my husband and I travelling this time I haven't done any further investigation on the accommodation. Thanks Beth ... more
Venice - Florence - Rome
Posted by MsChanChan, Dec 30, 2009
... spend the rest of my vacation in Rome until April 20th early morning. Can anyone suggest what i can do in Florence? i am not too into Art, and i don't know much about Florence. My husband would like to drive a car to drive some smaller town. is ... more
Posted by MsChanChan, Dec 31, 2009
... plan to just go there as well. but i also think if i am in Florence, i would liek to go to Pisa by train. sydneynick, i like your idea as well. can you tell me how much would that cost to rent a car? any good car rental company ... more
Posted by vteotl, Dec 31, 2009
Don't go to Florence just because it's a "popular place." Life is too short, vacation days are too few, to be visiting places just because.... It's OK to return to Ontario and say, "Yes I went to Italy. I didn't see Florence." ... more
Vacation Rentals by Owner Tuscany
Posted by Jayhawk68, Dec 29, 2009
We (2 couples) are looking to rent for a month in late spring in the San Gimignamo area to use as a base for day trips. Has anyone used Vacation Rentals by Owner to secure a place with positive results? Thanks for any suggestions. ... more
Posted by UsaKate23, Dec 29, 2009
VRBO is wonderful! We have used it several times in the states and in Europe and have never been disappointed. We , too, are planning a month in Tuscany in 2011. We will use this website for our rental. Good luck and enjoy... more
Posted by UsaKate23, Dec 29, 2009
VRBO is wonderful! We have used it several times in the states and in Europe and have never been disappointed. We , too, are planning a month in Tuscany in 2011. We will use this website for our rental. Good luck and enjoy... more
Unusual request about hotel payment?
Posted by sydneynick, Dec 26, 2009
... 30% of a week's rental. And sometimes this cannot be paid by credit card as the apartment owner is an individual who does not have a card merchant account. But even then, I would wonder why the owner could not take PayPal. I would never pay the full rental in advance ... more
Posted by ganu76, Dec 26, 2009
... would never pay the full rental in advance. Even if this is not a scam, you have no leverage if the apartment is not as advertised." --------------- Exactly, Sydneynick. I'm not thinking that this is *necessarily* a scam, but who's to say that I'd be able to get ... more
Go to Grosseto Forums »
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns