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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

Compare 723 Villas in Stigliano with updated reviews, rates, and availability.

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 private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking
Pool

Beautiful private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Beautiful private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking
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, (59)
"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
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (101)
"The whole family were together and enjoyed the beauty that surrounded us. It was a wonderful place that made for wonderful memories."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Macinella Friendly and Artistic apartment "Sunflower 1"
Pool

Macinella Friendly and Artistic apartment "Sunflower 1"

9.0 out of 10, Wonderful, (21)
"Traditional accommodation in a great location. In the middle of the sweet Tuscan hills. Very nice property, ambience Italian warmth and great atmosphere. always gladly again..."
Macinella Friendly and Artistic apartment "Sunflower 1"
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 pool, WIFI, TV, patio, panoramic view, parking, close to San Gimignano
Pool

Apartment in villa with pool, WIFI, 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 pool, WIFI, 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
Private Villa with private pool, WIFI, A/C, TV, patio, panoramic view, parking, close to Montalcino
Pool

Private Villa with private pool, WIFI, A/C, TV, patio, panoramic view, parking, close to Montalcino

Private Villa with private pool, WIFI, A/C, TV, patio, panoramic view, parking, close to Montalcino
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 Stigliano cost?
Prepare to pay between and per night for a villa in Stigliano. Whatever your budget, a fantastic stay is only a few clicks away on 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 Stigliano?
Choose from 723 villas in Stigliano. No matter if you’re taking a trip with the kids or planning a getaway with your buddies, Expedia can help you find the right space for your whole crew.
Why book your villa in Stigliano with Expedia?
We think that vacations shouldn’t be complicated, so if you’re searching for villas at an affordable rate, Expedia is here to help. Keep the budget under control and opt for an all-inclusive stay, or splurge on a high-end villa to spoil your favorite people. Our search filters make it easy to secure a property in Stigliano that fits your needs.