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IN TOWN! LARGE TERRACES & VIEWS of Vineyards & Olive Groves - Walk to Centre!

Bedrooms 4
Property type house
Minimum Stay 7 nights

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Minimum Stay
7 nights

About the property

4 Bedroom/2 Bath House nestled in the Hill with Spectacular Tuscan Views

Casina Pellegrino - Tuscan Villa.

A charming three tier house nestled in the sun kissed hills of Montepulciano, Italy. Enjoy gorgeous views in a perfect location that is less than a few minutes walking distance from the main Squares and the downtown areas. The house sits right outside the Medieval City Walls which means you get unobstructed, picture perfect views of the region with those Olive groves and vineyards right from your balcony and terraces.

Imagine waking up to breathtaking views of the Tuscan hill country from your private balcony or window. Open the French doors leading to the large terrace where you can enjoy breakfast lunch and dinner at your own pace. Appreciate the local wine, olive oil, bread and cheese so close in town. Lounge under the Tuscan sun, on a comfortable chaise with a glass of wine in your hand overlooking the 3 nearby lakes shining in the distance. Walk over to the medieval town center and visit the 16th century monuments, local specialty shops, sit in the main square to drink an Italian Espresso and listen to a free classical music concert. On your way back home, indulge in a homemade Gelato.

The house is big enough to accommodate and sleep up to 10 people comfortably. It is fully renovated with modern amenities, includes 2 separate full bathrooms, including a bathtub with view over the hills. In a town where parking is scarce and comes at a premium, you will be able to park 2 cars in dedicated spots in front of the house. The kitchen is fully equipped and allows you to cook fresh meals using local ingredients from the farmers market. Or if you want, visit one of the many restaurants nearby and sample some delicious 'Pici' a Tuscan specialty.

Montepulciano, located right in the middle of the Tuscan Region, is an important medieval and Renaissance hill town in the province of Siena. With its elevation of 2000 feet and surrounded by Olive groves and Vineyards, it provides an amazing combination of views, world renowned wines, culinary experiences and rich history. The town is located 45 minutes away from Siena, an hour and a half from Florence and two hours away from Rome.

**Seasoned travelers tip:

Many tourists come to Italy each year but only a few Insiders understand Montepulciano is the perfect location because it is central and so close to many big cities and popular places in and even outside of Tuscany! It is quaint enough however, to give a true and very authentic experience of what Italy stands for: Food, Wine, Beauty, History, Basking Sun and some definitely fun and very welcoming people!

To truly experience and enjoy this country it is best to Rent a Car and use Montepulciano as a base from which to organize day trips to the most popular cities: Florence, Rome, Siena, etc. You will not only wake up to unparalleled views from the spacious house an get a lot more for your money but you will also avoid the hustle and bustle of the big metro areas. So, Instead come and enjoy the dolce vita (sweet life) in a peaceful and traditional italian town that has served as background to many popular movies (Under the Tuscan Sun, The Twilight saga, Letters to Juliet, English Patient and more.) From the you can walk to many historical markers and enjoy the day at your own pace or simply take the car and do a scenic drive on to the next cute town of Pienza, visit a castle in Montichiello or go vineyard hopping for example. There are so many options you can choose from, that is why Montepulciano and Casina Pellegrino, offer you the best of Italy no doubt.

Keywords: House, Spacious, Villa, Amazing Views, Under the Tuscan Sun, Vineyards, Olive Groves, Kitchen, Montepulciano, Tuscany, Siena Region, Close to Rome, Siena, Florence, Val D'Orcia, Val di Chiana.

More Details

Erika Pellegrino
Member since: 2011
Speaks: english, french, german, spanish, portuguese, italian
Response time:
Within 12 hours
Response rate:
Calendar last updated:
December 30, 2016

About Erika Pellegrino

My husband and I are an adventurous and energetic couple with 2 children living in Austin Texas. We chose Montepulciano as our second home in the Winter/Spring because we love the country, traveling, enjoy food and wine and of course: sightseeing. When we travel, we try to immerse ourselves in the local culture. We have successfully done that in this lovely town and we are ever so lucky to discover more and more amazing wonderful places in each of our journeys that we gladly share with our guests in our insider's guide.

Erika Pellegrino purchased this house in 2010

Why Erika Pellegrino chose Siena Province

Montepulciano is a fantastic town in the heart of Tuscany, which has so much to offer: Views, food, wine, historical background. The people in Montepulciano are so friendly that you instantly feel yourself at home there.

What makes this house unique

There is nothing better than to sit down with a glass of wine and see these breathtaking views. The town of montepulciano has so much history and all the wonderful small towns around it are so unique, one would never get bored while staying there.


Wonderful! 4.9/5 -
(21 traveler reviews)

IN TOWN! LARGE TERRACES & VIEWS of Vineyards & Olive Groves - Walk to Centre!
average rating of 4.904762 based on 21 reviews

Walk to town with a view. Amazing!

  • 5 of 5

After years of staying in various places all around the world, I can say without a doubt that this is the best place we have stayed in. Great location, lots or room (too much for us), clean, everything works, detailed information provided, lots of accessories (dishes, etc) and an amazing view to top it all off. Incredible.

  • Submitted: Aug 17, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: Grazie mille!! I am so pleased to hear you had a fabulous vacation and above all that our place has exceeded your expectations. Seems you are a seasoned traveler and your comment about this being the best place for you thus far goes a long way and is very much appreciated. We try our best to make all of our guests happy and comfortable with all the extras but really the view and the location take care of the rest. We hope to have you back soon!! Regards Erika:)
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  • 5 of 5

After two weeks of traveling throughout southern France and Italy, we landed at this location in the beautiful Tuscan region of Italy. The home was the perfect place to recharge ourselves. The sweet home has a true sense of enchantment throughout; from its views & architecture to the thoughtful way the homeowners have decorated and furnished it. I enjoyed being able to park our car securely here and easily walk up into the old town city center for shopping and delicious food. We had several homemade meals with our family here; the kitchen and dining areas were perfect - both inside and outside.

There is a lot of space in this home; an upstairs with a full bathroom and two bed rooms, each with two twin beds (or one kind beg depending on configuration). A downstairs that includes two twin beds, two comfortable futons and also a room with a king bed and a beautiful window view of the vineyard filled valley and hills (can also see several lakes from this view). The terraced balconies were perfect for morning and evening relaxation with gorgeous views that no camera can adequately capture.

The homeowners were extremely helpful and readily available for communication. If you're after an enjoyable Tuscan getaway, this is a magical destination. Thank you!

  • Submitted: Aug 13, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for taking the time to write such a thorough and descriptive review of our place. Speechless... We try hard and are always so happy to hear when our guests had an incredible time in our home. Best of all, knowing that though we may think we have the perfect location and a cozy yet larger than your usual rental in Europe, we are not that biased after all because everyone's comments reflect the same thoughts . Grazie again as we hope to host you and your friends again in the future . Casina Pellegrino
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United States

Postcard Come to Life

  • 5 of 5

Myself, husband, and 2 boys (12 & 17) are at the tail end of a one month trip through Europe. We have stayed at 8 places so far in Spain, France, Italy, and Switzerland. Staying here was a define highlight to our trip.

Many of the places we've stayed feel like rentals. This felt like home. All the utensils and dishes necessary for a home cook meal, a private parking spot, random extras like novels and travel books to read, framed pictures of the gorgeous Tuscany region, drawers, desks, and clothes hanging racks... and the there is the DROP DEAD GEORGEOUS VIEWS! ...from the bedrooms, bathrooms, terraces, living room. Seriously, I took at least two dozen photos trying to capture it, but they don't do it justice. This house is sitting on a hill overlooking the most beautiful view in Tuscany... my humble opinion.

The location is ideal too. You can walk to the undrivable historic center, and you have the country in your backyard. The town is sweet. We enjoyed the Farmer's market, a yummy little pastry shop down the road, dinner at a place Erika recommended, and soaked in the view as much as we could. What a gem!!

  • Submitted: Aug 10, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Wow thank you! So very happy to hear this was the highlight of your trip through Europe. Having kids ourselves we can perfectly relate how sometimes you just wish for a place to sit down and let the views take over to relax. We hope you continue to have a pleasant and safe trip thru out. All the best. Saluti The Pellegrinos
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Great location in Montepulciano with nice amenities, but no A/C, so a bit uncomfortable sleeping

  • 3 of 5

It was great to have a parking spot right in town -- very convenient location. The valley views are spectacular and exactly as advertised; So pleasant for adding beauty and tranquility to evening wine hour or morning coffee. We felt very safe. Kitchen is well appointed. Owners are polite and hospitable. Some loud noise from nearby roads most of the early morning and evenings that made it difficult to sleep. There is no air conditioning and, although the temperature falls in the evenings, the 2nd floor bedroom air flow is not enough to make sleep cool and comfortable. The shower hot water ebbs and flows between not on at all, and scalding. Overall a nice spot to call home while seeing southern Tuscany, with some less-than-ideal circumstances. I would recommend this location for all the non-hot months (July and August).

  • Submitted: Aug 6, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: First of, thank you so much for taking the time, it is always appreciated and can only help improve things. I am glad to hear the views, location and parking provided happines and convenience during your time in Montepulciano. I am terribly sorry to hear you experienced any inconvenience as I stay in constant communication with guests and have not had issues unresolved. So I truly wish I could have been notified to help alleviate in any form or way. We do not have AC as the house is inside the mountain and it has not been an issue but we have considered adding some just in case in the upstairs rooms. We do however have fans that have helped guests just fine in the past and we just had another family leave this week with no issues. I can see however that the weather may have been unusually extreme during your stay. Again I'm sorry to hear that. As to the water we will send someone to look at it and make adjustments if necessary (I must admit the European water systems are quite complex at times and this home is an older build (adding to the Italian charm) but as per the instructions I send all guests prior to arrival for the shower specifically there is a trick. Either way I will see to it as usual that we make improvements whenever possible. Thank you and again I apologize as I hear this for the first time and wish I could have been given the opportunity to guide and acommodate. As you can see we've had happy guests all along and this experience is not the norm. We hope we can host you again one day as I'm sure we would turn this into a positive five star stay. All the best! Erika
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Location made our vacation!

  • 5 of 5

Just a quick note to tell you what a wonderful time we had staying at your home in Montepulciano. We absolutely loved the area and your home was perfect for the 7 of us. I'm still dreaming of the views and ....the food of course :).

We all agreed that La Casina and it's perfect location really made our vacation. Each evening we would walk up the stairs into town and enjoy walking through the streets to the Piazza Grande and window shopping. Something we never would have done if we'd stayed farther away. You really have a wonderful spot there.

Thank you again and I hope to spend more time in Italy soon!

  • Submitted: Jun 3, 2016
  • Stayed: May 2016
  • Source: HomeAway
Owner's Response: Grazie mille Emily! We very much appreciated reading your comments and are always so happy to hear that we are not biased and the only ones to think we have a great place and such a perfect location:)! Over tbe years, we keep discovering even more hidden gems and all so close in the area that it just keeps getting better. Thank you for taking the time to let others know how convenient the Casina was. I will also make sure to include the recommendation of that Chef and his cooking you sent me via email, for others to benefit from. We Hope to have you back soon!
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Evergreen, CO

Very Convenient - Great Views

  • 5 of 5

La Casina was the perfect base for our party of five to explore the Tuscan countryside. We even took a trip to the Island of Elba and enjoyed every minute. The great advantage of having a villa just outside the walls of Montepulciano made it perfect to become a part of the community for our 4 week stay, and it was wonderful returning to the villa's outstanding views. All of the people of the town were wonderfully friendly and welcoming, even if we could only speak a smattering of Italian.

All of the information on the website regarding the villa is accurate. Though the villa sleeps up to 10 people, we found 5 to be more desireable with two bathrooms and making for a more private sleeping arrangement. Erika was extremely responsive to all of our questions and she made excellent recommendations for things to do and see. We especially enjoyed weekly picnics at the Cugusi dairy farm off the road to Pienza and were delighted to find their cheeses available in Montepulciano as well. We enjoyed stopping by for drinks and having meals occasionally at Trattoria di Cagagno, which is so convenient to the steps into the city. We also followed Erika's advice and enjoyed a sunset dinner at Osteria del Borgo, conveniently located just off the Piazza Grande.

Unless all you want to do is visit Montepulciano during your stay, a car is essential. It took us to the other hill towns, cooking class at La Ciccolina (highly recommended), and a lovely wine tasting with author Jennie Criswell at the Poliziano winery.

Thank you, Erika, for letting us share La Casina!

  • Submitted: Oct 19, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
Owner's Response: It is always such a pleasure to hear our guests enjoyed their time and I am so grateful that you took the time to share your long stay at the Casina and its perks. We enjoyed having you and your party stay and very much agree with you that being right outside of the city walls allows not only for Unrestricted views but also the practicality of plenty of parking while being just steps away from the city center. We hope you will consider coming back to montepulciano and the Casina one day and wish you all the best. Saluti Erika:)
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Nearest Airport
30 Miles
Siena 30 Miles, Perugia 37, Pisa 80, Firenze, Rom
Nearest Barpub
0.01 Miles
Just a few steps away inside the city walls :)
Nearest Ferry
68 Miles
Nearest Train
8 Miles
Montepulciano Stazione or the one in Chiusi about
Nearest Motorway
10 Miles
A1 Valdichiana
Nearest Restaurant
0.01 Miles
So many just a few steps around the corner!
Nearest Ski
30 Miles
Monte Amiata
Nearest Beach
60 Miles
Car: not necessary

Wine tasting, Vineyard hopping, Olive oil tasting, Local foods, Pecorino, Grappa, Amazing restaurants, Historical monument Sightseeing, Weekly farmers' market, Classical music concerts, Operas, Theater, Movie Pilgrimage: Twilight - Under the Tuscan Sun - Letters to Juliet - English Patient etc..., Cooking class, Fiat Cinquecento club, Palio de Siena, Bravio delle Botti Festival.

Distances to other great places:

Castiglione del Lago - 24 km;

Arezzo - 53 km;

Siena - 61 km;

Perugia - 67 km;

Florence - 110 km

Lucca - 180 km;

Rome - 177 km;

Pisa - 214 km


Rates & Availability

Montepulciano House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
7 night minimum stay

Additional information about rental rates

5+ppl addtl deposit refn $250
Refundable damage deposit $250
Cleaning Fee $50

Minimum 1 Week Stay Required.Up to four people $1500 per week with a $250 deposit. If over 4 people then, Addtl Large Group Rate Deposit applies (5 to 10Max occupants) Regardless of Season. To reserve a min payment of 50% from total plus a US $250 or $500 (5+Group Deposit) Fully Refundable Damage Deposit Fee are required at this point. Grazie :)

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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Montepulciano House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Included
Location Type:
  • Downtown ...
  • Lake View
  • Mountain View
  • Adventure
  • Budget
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Fireplace
  • Garage ...
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Mobile Phone
  • Parking ...
  • Parking Off Street ...
  • Towels Provided
  • Washing Machine
  • Wood Fireplace
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Stove
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • One bathroom downstairs with a shower, comode and bidet on one side and separated thru a door from it, is the sink/full size mirror for privacy. A Second larger Full Bathroom can be located upstairs with a Baththub, comode and bidet as well
  • 4 Bedrooms, Sleeps 10
  • Bedroom 2 - 2 twin/ single , Ideal for Kids in Twin Beds or a couple can convert to King
    Bedroom 3 - 1 queen , Queen Bed in Studio with French Doors and a lovely View
    Bedroom 1 - 1 king , VIEWS w Balcony has TwinBeds that we easily convert to KING
    Bedroom 4 - 2 twin/ single , LARGEST Area/downstairs w. twin Beds and QueenSofa +Bathroom
    Convertible bed(s) - Most Rooms have Twin Beds can convert to KING plus 2 sofabed
  • Two Main Bedrooms upstairs (Twins that can be KING) One with Balcony the Other has view of City Walls -- These rooms share Larger Bathroom with Tub, Bidet and Beautiful Views Downstairs there is a Study with comfortable Queen gorgeous View and large French Doors (Romantic and Ideal for Couples) Downstairs has also an additional Large Area with two additional Twin Beds and Terrace Views. The Downstairs shares the Main Bathroom with Shower, Bidet, etc and gorgeous Views of course. If needed there is also a Futon Bed in the Living Room for the last 2 Guests. Sleeps 8 Comfortably and 10 and most with the Living Room arrangements IN ALL Queen (1), Twin or Single Beds (6), Sleep Sofa or Futons (1) Arrangements can be as follows: 2 Couples with 4 Children- TOTAL 8 GUESTS 1 Couple Upstairs in converted King Bed with their Kids Across in Twin Beds - Sharing Bathroom Upstairs 1 Couple Downstairs Queen Bed in Study and their Kids on the other side on Twin Beds - Sharing the Main Bath
  • Books ...
  • Balcony
  • Deck / Patio
  • Lawn / Garden ...
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible ...
  • arboretum
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • recreation center
  • restaurants
  • ruins
  • water parks
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • freshwater fishing
  • hiking
  • mountain biking
  • mountain climbing
  • swimming
  • tennis
Huge outdoor Terraces, Lounge Chairs, Office desks, Vineyard views, Olive Grove views, 2 minutes walking distance to historical center.

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