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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 1724 Villas in Monteriggioni with updated reviews, rates, and availability.

Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (34)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (47)
"My wife and I both loved this property. The host (Gianni) was responsive to any questions we had. Gianni's parents (Carlo & Paula) live in the adjacent main house and were extremely hospitable. We honestly couldn't have asked for a better location or host/s. We would recommend this property to anyone that wants to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Il Boschetto an oasis of peace and nature in Siena
Outdoor pool

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (31)
"The location was excellent, 30 minute walk (2.1 km) to the main gate of Siena or 15 minute bus ride (bus stop 25 meters from the house). The home is beautiful, lots of amenities, it was very rustic. The pool area could use a good trimming, the online photos showed the property better than it actually was but not too far off."
Il Boschetto an oasis of peace and nature in Siena
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Outdoor pool, a heated pool

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (87)
"I wish we could have stayed longer; such a beautiful location. The villa was very nice and comfortable. We enjoyed meals prepared by Serena twice during our visit; she cooked multi-course dinners that were delicious. Highly recommend the property and Serena’s cooking. We look forward to going back!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Villa with view and private pool
Outdoor pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa Dipendenza, Historic Holding with wonderful swimming pool
Outdoor pool

Villa Dipendenza, Historic Holding with wonderful swimming pool

10.0 out of 10, Exceptional, (36)
"We spent a week at this charming property and had an absolutely magical time with friends. The house was cozy and comfortable, with a beautiful balcony perfect for enjoying evening meals. The shared pool offered breathtaking views, and the other guests were incredibly friendly, adding to the warm atmosphere. Our host, Eloise, was exceptional—her hospitality and attention to detail made our stay even more special. She provided wonderful restaurant recommendations that we thoroughly enjoyed. We...
Villa Dipendenza, Historic Holding with wonderful swimming pool
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Outdoor pool, sun loungers

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (96)
"Peaceful, quiet, tucked away beautiful in the beautiful Tuscany area. Would stay there again. Excellent property!"
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Villa Simone - Luxury Villa in San Gimignano, Chianti
Spa

Villa Simone - Luxury Villa in San Gimignano, Chianti

9.8 out of 10, Exceptional, (8)
Villa Simone - Luxury Villa in San Gimignano, Chianti
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor pool

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Beautiful private villa for 4 guests with WIFI, A/C, pool, TV, terrace and parking
Pool

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

9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Beautiful private villa for 4 guests with WIFI, A/C, pool, TV, terrace and parking
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Outdoor dining

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

9.4 out of 10, Exceptional, (51)
"Great host, location as we wanted in Tuscany. We had villa for only our family and it was enjoyable. It is a good WiFi there, TV, kitchen. And everything you need. "
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Outdoor pool

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (39)
"Villa Sarah is one of those once in a lifetime experiences. Even after seven blissful days, we still couldn’t believe we had the privilege of staying here. The views from the house of the rolling Tuscan hills and enchanting San Gimignano in the distance is a sight we will all treasure forever. The house is so thoughtfully designed and furnished by the owner, Gabriele. You really feel at home, but with every luxury, including five whimsical bedrooms with en suite bathrooms, stunning views around...
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Authentic Tuscan country house, dating back to around the year 1000
Outdoor dining

Authentic Tuscan country house, dating back to around the year 1000

9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic Tuscan country house, dating back to around the year 1000
Historic mill with private swimming pool
Outdoor pool

Historic mill with private swimming pool

Historic mill with private swimming pool
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Exterior

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (46)
"We had a great stay here. All of us really enjoyed the location!"
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
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, (56)
"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
Exclusive villa with park and private swimming pool in Siena
A heated pool

Exclusive villa with park and private swimming pool in Siena

10.0 out of 10, Exceptional, (1)
"Ottima esperienza accompagnata dalla cordialità dei proprietari. La villa è una comoda base per visitare Siena e i dintorni. Al rientro si può godere della piscina e del panorama delle colline tra gli ulivi. La proprietaria è un'ottima cuoca se si desidera una vera cena toscana"
Exclusive villa with park and private swimming pool in Siena
Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Fridge, microwave, oven, stovetop

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
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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Other property types in Monteriggioni

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (47)
"My wife and I both loved this property. The host (Gianni) was responsive to any questions we had. Gianni's parents (Carlo & Paula) live in the adjacent main house and were extremely hospitable. We honestly couldn't have asked for a better location or host/s. We would recommend this property to anyone that wants to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
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
Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
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.

Frequently asked questions

How much do villas in Monteriggioni cost?
Villas in Monteriggioni cost between and per night. These stays give you the privacy of your own space at a price that’s friendly to your wallet. 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 Monteriggioni?
Monteriggioni has 1724 villas to pick 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 Monteriggioni with Expedia?
We think vacation time should be a breeze, so if you’re searching for villas at a nice price, Expedia is here to help. Keep the budget under control and choose an all-inclusive stay, or splurge on a 5-star villa to spoil the ones you love most. Take advantage of our search filters to find a place in Monteriggioni that matches your needs.
How can I find cheap villas in Monteriggioni?
A fantastic way to track down cheap villas in Monteriggioni is with Expedia’s handy filter tool. Refine your search results by budget, star rating and amenities to grab unbeatable deals in only a couple of clicks.