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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Villas in Pentolina

Villa Costa, Stunning Villa in the heart of Tuscany.
Exterior

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (33)
"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.
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Outdoor pool

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Outdoor pool, sun loungers

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

9.6 out of 10, Exceptional, (30)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Terrace/patio

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

9.2 out of 10, Wonderful, (7)
"Only regret is that we couldn’t stay longer to explore more of Tuscany. Wish weather was a bit warmer to use the beautiful pool. Overall beautiful home with upscale features! We really enjoyed our stay!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (21)
"We were a group of 4 families with toddlers and loved our stay at the villa! Alessandro was an excellent host and very responsive. The views and pool are stunning, and the house is clean and decently equipped. Highly recommended for a group stay in Chianti!"
BEAUTIFUL VILLA with private Pool in the heart of Chianti
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Outdoor pool, a heated pool

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

10.0 out of 10, Exceptional, (60)
"Stay was excellent, a great house. Owners were super helpful. A property with over 100 olive trees. If I return this is where I will be 😎"
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor pool

Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly

9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena
Independent RELAX villa 2-5 people 12 min from the sea
Fridge, microwave, oven, stovetop

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 with unique view of Siena with private pool
Outdoor pool

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
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor dining

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Fireplace

Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14

9.8 out of 10, Exceptional, (7)
"Lovely well-equipped home with space and easy privacy for family groups. Lovely property with local flora and magnificent views. Pool pleasant but shallow - for cooling off but not swimming. Note: house is large and has separate (entrance, parking,property) rental section. Pool only for you however and still good privacy."
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage
Outdoor pool

Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage

10.0 out of 10, Exceptional, (132)
"Wonderful outdoor space, lots of rooms and space, and amazing and helpful owner. Bellissimo!"
Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage
Villa Larniano, With Private Pool And View On Vineyard
Outdoor dining

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
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Outdoor dining

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

10.0 out of 10, Exceptional, (8)
"Podere Ferrale is just amazing. We were a group of 8 people and Sam was an amazing host from start to finish. Our parents had big birthdays and Sam and her husband cooked a wonderful dinner for them. We would definatley come back!"
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Apartment in villa with WIFI, pool, TV, patio, panoramic view, parking, close to San Gimignano
Pool

Apartment in villa with WIFI, pool, TV, patio, panoramic view, parking, close to San Gimignano

8.6 out of 10, Excellent, (8)
"nice hosts, but a little bit in the years"
Apartment in villa with WIFI, pool, TV, patio, panoramic view, parking, close to San Gimignano
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Terrace/patio

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Villa luna with pool and garden near the center of Siena
Fridge, microwave, oven, dishwasher

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
Outdoor pool

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

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

9.4 out of 10, Exceptional, (58)
"Lovely villa, great host. We really enjoyed our stay. "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
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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Frequently asked questions

How much do villas in Pentolina cost?
Rates for villas in Pentolina range between and per night. No matter your budget, you can find a place that suits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Pentolina?
Pentolina has 550 villas to select from. Find your next perfect stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
Why book your villa in Pentolina with Expedia?
We think planning a vacation shouldn’t be hard, so if you’re on the lookout for villas at a great price, Expedia has your back. Save some cash and pick an all-inclusive stay, or splurge on a luxe villa to spoil your nearest and dearest. Our handy filters make it simple to find a place in Pentolina that suits you best.