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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
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22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Villas in Roccastrada

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Relax in a serene outdoor space surrounded by lush greenery and a tranquil body of water.

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (102)
"Beautiful home, beautiful views. "
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Stunning Villa: 24 guests, private SwimmingPool
Experience the serene atmosphere of our traditional garden, surrounded by a variety of plants and a small pond.

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
Villa Costa, Stunning Villa in the heart of Tuscany.
Situated in a rural countryside setting, this charming home features a traditional stone building with a sloped roof.

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Relax in style on the patio, surrounded by lush views and a refreshing pool.

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (10)
"We were two couples looking for an authentic Tuscan experience in the gorgeous countryside. The location is well suited to travel to Montalpucino, Chianti, San Gimignano, Volterra, Pisa and Florence. Both Mido and David were very attentive towards making our visit comfortable . A gorgeous building with high quality style and finishes. A top contender for best vrbo property I have ever visited. Thank you!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Enjoy al fresco dining with a view of the landscaped garden and distant mountains from this outdoor grill.

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (60)
"Lovely villa, great host. We really enjoyed our stay. "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Guests can relax on the outdoor bench amidst a serene garden with flowering plants and a tree.

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (33)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Villa with unique view of Siena with private pool
Stroll through the beautifully maintained garden, featuring a variety of flowering plants and a charming, rustic building with an arched doorway.

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
House / Villa - Bagno di GavorranoHouse with garden
Relax by the serene pool surrounded by lush greenery and a palm tree.

House / Villa - Bagno di GavorranoHouse with garden

10.0 out of 10, Exceptional, (6)
"We stayed 2 weeks and it was wonderful! The house is very nice and spacious as is the garden. And the swmingpool is great of course, especially during the warm days. Location is great as well: close to beaches, lovely towns and restaurants."
House / Villa - Bagno di GavorranoHouse with garden
Independent RELAX villa 2-5 people 12 min from the sea
Enjoy a meal al fresco on the patio, surrounded by lush greenery and a serene garden.

Independent RELAX villa 2-5 people 12 min from the sea

9.8 out of 10, Exceptional, (18)
"Die Vermieter waren überaus freundlich und sehr hilfsbereit. Die Ausstattung des Hauses ist sehr gut. Man kann sein Auto auf privatem Grund abstellen. Das Haus bietet einer Familie einen sehr ruhigen Urlaub, man ist trotzdem in 10 Minuten in der Altstadt oder in 5 Minuten beim sehr gut ausgestatteten Supermarkt COOP. "
Independent RELAX villa 2-5 people 12 min from the sea
Villa Larniano, With Private Pool And View On Vineyard
Enjoy al fresco dining with a view of the lush landscape from this outdoor dining area.

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Relax in a shaded seating area surrounded by lush greenery and countryside views.

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Holiday house with private garden and pool in a typical Tuscan hamlet.
Dine under a picturesque pergola surrounded by lush gardens and a stone wall.

Holiday house with private garden and pool in a typical Tuscan hamlet.

10.0 out of 10, Exceptional, (2)
"We had a fantastic two-week stay with our (extended) family.The house is perfect for three couples – each had their own bedroom, bathroom, and toilet.We didn’t need the extra room with two single beds.The house is even better than it looks in the photos.It has everything you need – spotlessly clean and very practically laid out.Beautiful Roman-style pool with plenty of loungers, a garden dining set, and a large tree providing lots of shade.The covered terrace next to the kitchen was the perfect...
Holiday house with private garden and pool in a typical Tuscan hamlet.
Villa luna with pool and garden near the center of Siena
Stroll through the serene courtyard surrounded by lush potted plants and a charming building with an arched entrance and balcony.

Villa luna with pool and garden near the center of Siena

9.0 out of 10, Wonderful, (27)
"We had a great time "
Villa luna with pool and garden near the center of Siena
villa con vista panoramica
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

villa con vista panoramica

9.0 out of 10, Wonderful, (2)
"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"
villa con vista panoramica
panoramica casa con piscina privata
Relax by the serene pool surrounded by lush greenery and distant hills.

panoramica casa con piscina privata

7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
The price is NZ$356
includes taxes & fees
16 Aug - 17 Aug
panoramica casa con piscina privata
Delightful villa in the heart of Tuscany
Relax by the serene pool surrounded by lush greenery and rolling hills.

Delightful villa in the heart of Tuscany

10.0 out of 10, Exceptional, (54)
"We LOVED staying at villa le Bolli. We had an intimate wedding here and it was absolutely beautiful. The property is clean with great upkeep and amazing views. Pierre went above and beyond to meet our needs. Would love to return for an anniversary."
Delightful villa in the heart of Tuscany
Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
Relax by the spacious outdoor pool surrounded by lush gardens and trees.

Historic Villa Ferrano has modern amenities, ideal for medium-sized events.

10.0 out of 10, Exceptional, (1)
"Amazing property. Very well run"
Historic Villa Ferrano has modern amenities, ideal for medium-sized events.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Relax by the serene pool surrounded by lush greenery and comfortable lounge seating.

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Tuscan stone villa with private pool surrounded by greenery
Relax by the serene pool surrounded by lush greenery and breathtaking mountain views.

Tuscan stone villa with private pool surrounded by greenery

10.0 out of 10, Exceptional, (95)
"Lovely place, we felt very welcome"
Tuscan stone villa with private pool surrounded by greenery
Villa Dipendenza, Historic Holding with wonderful swimming pool
Escape to a serene retreat surrounded by lush greenery and a tranquil atmosphere, featuring a swimming pool and terraced fields.

Villa Dipendenza, Historic Holding with wonderful swimming pool

10.0 out of 10, Exceptional, (39)
"Our host, Eloise, was incredibly gracious and welcoming! We highly recommend the homemade dinner and wine that she served us one evening. A beautiful property! We would love to come back some day."
Villa Dipendenza, Historic Holding with wonderful swimming pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Roccastrada Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"We have always loved Sienna . Love the history , the architecture . "
Leane 1-night trip
Posted 3 days ago
Hotel Athena