Villas Montemassi

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Farmhouse with pool in Tuscany

Montemassi villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$494

Villa Norma

Montemassi villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 52 minutes

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$482

Great rentals within 20 miles that match your search

ROCCAMARE - spacious villa by the sea

Castiglione Della Pescaia villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

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$971

ROCCAMARE Villa with pool and private beach

Castiglione Della Pescaia villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,606

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$124

home among the olive trees

Massa Marittima villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$318

Lorenza house

Marina di Grosseto villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 39 minutes

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$99

Villa Le Bolli: a vacation like at your home!

Radicondoli villa

  • 12 bedrooms
  • 14 bathrooms
  • sleeps 36

“A beautiful place to spend great moments with friends and family” We have been three families, a couple and some friends arriving on their own. It was one of the most relaxing, funny and wonderful holiday we have ever spent. The kids loved their time at the pool, the garden, with dart, billiard, ping-pong and table soccer and of course with the cat "Luigi". We adults had lots of time for chatting, laughing, joint cooking and eating, relaxing and some sports. The professional and big kitchen is a real asset. Albeit the nearby very fine and cosy restaurants, we usually preferred staying among us in the villa. Both, in sun shine and rain, the villa offers all you need for a great time in the big group (a big salon with open fire, several living and dining rooms indoor, the big and well-kept garden, main terrace, barbeque and pool outdoors). There are however also enough spaces to retire to, such as a hammock below a beautiful old oak, hidden benches in the garden, comfortable sofas here and there, and of course the spacious sleeping rooms, each with individual features and great views over the Tuscan landscape. We definitely can recommend this place!

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Price per night from

$1,976

casa con piscina panoramica

Chiusdino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$149

casa con piscina

Chiusdino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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$149

Villa in secluded grounds of 1 hectare

Gavorrano villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$247

Giunia

San Lorenzo a Merse villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 27

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Price per night from

$2,739

Private Tuscan Villa

Radicondoli villa

  • 12 bedrooms
  • 13 bathrooms
  • sleeps 24

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Poggio alla Rocca

Casale di Pari villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

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$2,224

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

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Price per night from

$3,606

Sea

Murlo villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Farm the castle area.

Chiusdino villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

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Price per night from

$671

vegoia

Campagnatico villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Time in Tuscany - The Villas at Podernuovo

Castel Del Piano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Podernuovo offers a unique opportunity to see the real Italy in” Service: Alvina and Umberto are the perfect hosts, friendly and helpful, well-informed as to what to do and what to see. The accommodation: The villas are superbly appointed with every modern appliance, yet from the exterior they retain their rustic charm. All the windows overlook the vineyard and olive groves and the spacious terraces are the perfect spot to enjoy a glass of Umberto's wine after a day of exploring. Location: Podernuovo is well situated to visit the many medieval villages Tuscany is known for. We have had 10 stays at Podernuovo and have enjoyed wonderful day trips to Collodi, the town of Pinocchio Pistoia, Sant'Antimo abbey, to listen to the monks Gregorian chant and Saturnina to luxuriate in the thermal baths. Alvina and Umberto's local knowledge also extends to the most novel and interesting restaurants in the region. The village of Castel del Piano is a 10 minute stroll up the hill and boasts excellent supermarkets, cafes and bars. What did we like best? My husband and I love everything about staying at Podernuovo as witnessed by 10 stays there! Perhaps however, the fact that it is truly unique Italian experience, 'off the beaten track' in a sense and in a place where tourists do not abound (and where villagers are friendly and welcoming), sets it apart from other villas we have stayed in. I simply can find nothing about Podernuovo that doesnt delight both of us. In fact, we are already planning our next visit for 2013.

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Price per night from

$359

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$115

Cozy Collection of Villas in Tuscany

Montalcino villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

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Price per night from

$1,705

Deal 2023 Private Tuscany villa with pool and jacuzzi near Siena for holiday

Montecastelli Pisano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$141

Casale at Petriolo-private pool

Casal di Pari villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 21 minutes

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$247

Schönes Appartement in historischer Villa mit Garten und Parkplatz.

Massa Marittima villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$99

Tuscany quiet view on the sea

Punta Ala villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 4 minutes

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$229

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$133

Meleta Company - Casa Archi

Roccatederighi villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$581

Villa Elisa

Poggio alle Mura villa

  • 11 bedrooms
  • 13 bathrooms
  • sleeps 30

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Price per night from

$1,937

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

Villa Montalcinello In Siena, Private Pool - Villa Montalcinello

Montalcinello villa

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 13

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Price per night from

$354

Valloria estate

Massa Marittima villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,235

La Sugherosa - Villa with sea view in Tuscany

Punta Ala villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$494

Big villa for 12 ppl. with swimming-pool at Roccamare

Pian di Rocca villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$1,121

Villa Lustignano

Lustignano villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$214

Villa Roccamarina Villa Roccamarina

Castiglione Della Pescaia villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 19

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Price per night from

$2,989

Poggio Tamantino, Villa con Piscina in Maremma

Grosseto villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,853

Villa in Maremma Toscana. Piscina Veranda e Giardino in Esclusiva

Gavorrano villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$309

Villa in Toscana

Monteverdi Marittimo villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

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Price per night from

$698

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