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Casamaggiore Rentals

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2,124 Houses

Comfortable Village House,in village location.

Casamaggiore house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$181

Private villa between umbria and tuscany with air conditioning and private pool

Casamaggiore villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$189

Great rentals within 20 miles that match your search

Beautiful Independent Tuscan Cottage For 2 With Spectacular Views

San Casciano dei Bagni cottage

1 bedroom / 1 bathroom / sleeps 2

“Views amazing, house beautiful and Village so friendly” We stayed for one week at La Ginestra and could have been there for so much longer. We loved it, the view across the valley is a wow and the house is so tastefully decorated and of high quality. The village is just two minutes walk away and has a fab pub and lovely restaurants. I am a Food Technologist so food is very important to me - the butchers in the old town was fab, sausages and ham just so delicious. We really did feel accepted everyone was just so friendly to us. We toured most days and saw some beautiful Tuscan towns. We loved everything about it. Bed so comfy and beautiful, bedding crisp and white.

Price per night from

$165

Villa in Tuscany near Montepulciano and Vald'Orcia

Chianciano Terme b&b

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$593

Charming Country Villa with Panoramic Private Pool

San Casciano dei Bagni villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$317

contryhouse near siena: Apartment 2 Person

Sinalunga apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$435

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$147

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$118

Villa Bagnaie

Lisciano Niccone villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$554

Charming apartment on Tuscany/Umbria border

Paciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$159

Typical house with lovely view and swimmingpool

Cortona house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$423

Typical house with private pool and stunning view

Cortona house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$423

VILLA ANTICO TABACCAIO PERFECT FOR GROUPS AND FAMILY REUNION! SPECIAL PRICE 2019

Panicale villa

7 bedrooms / 5 bathrooms / sleeps 16

“Excellent villa in a beautiful location” We were three families holidaying in this wonderful villa with our children, ages 9-16. The kids loved the pool and us adults enjoyed soaking up the Umbrian sun in the well-maintained gardens. We explored the local area-Montepulciano, Isla Maggiore and Castiglione del Lago (market Wednesday am). We also did Siena on the train. Would have liked to have done more,but a week is not enough. Katia was such a welcoming host,nothing was too much trouble. Thank you very much Katia, hope to see you in a year or two!

Responds fast! avg. 2 hours 54 minutes

Price per night from

$588

Stunning Tuscan/Umbrian Farmhouse - Infinity Pool

Piegaro farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$194

Rustic countryside farmhouse,authentic,homey,Views

Umbertide house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$53

Vacatoin Rentals at Le Celle Del Farinaio in Short

Cortona villa

6 bedrooms / 4 bathrooms / sleeps 14

“Charming place in Toscana. You will never forget your stay” Charming villas on the hills of the Trasimeno lake with beautiful scenery and relaxing. Time stops during the stay. Each has its place and benefits as it means facilities available: swimming, Mountain biking. Difficult to leave the house yet conveniently placed for exploring the treasures of Tuscany and Umbria. Mauro, the owner upon arrival, established a welcoming atmosphere and is at your disposal during your stay. Everything is perfect even last evening organized by our host. An unforgettable stay. Bravo Mauro (e toute la famaglia Tarquini). Grazie.

Price per night from

$353

Villa Oliveto

Castelmuzio villa

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$639

Casa Oliveto

Castelmuzio house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$671

Apartment with a great view on the ground of organic farm, infinity pool

Montegabbione apartment

2 bedrooms / 1 bathroom / sleeps 4

“Fabulous Time” My husband and 23 year old son stayed in one of the upstairs apartments for about one week October 2012. Franco and Bozena were wonderful host and hostess. The farm and apartment are exactly as presented. Simple but clean, great views from each terrace, and kitchen well supplied. The pool was beautiful but a little too chilly to swim in October. Franco cooked a wonderful 'saffron' meal for us and a German couple who were also staying at the farm. Lots of wonderful day trips from the farm. We hope to return very soon!!

Responds fast! avg. 3 hours 30 minutes

Price per night from

$100

Apartment with private garden, infinity pool, organic farm

Montegabbione apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$100

Studio "Rustic" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$83

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

6 bedrooms / 5 bathrooms / sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

Price per night from

$999

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$141

Apartment "Leonardo"in cortona's country (2bd)

Cortona apartment

2 bedrooms / 1 bathroom / sleeps 3

“A place full of charm” We were three friends Spanish for a week and the room was unforgettable. The functional and bright apartment, located in a beautiful place, we loved it. Lorenzo, the owner is a lovely person and always willing to help beyond what we expected. Car is necessary to explore the region, which is wonderful. We are delighted and indeed the place again. Lorenzo and Silvia Thanks for your hospitality and for all you know, even by my ineptitude, which I appreciate from heart. You are wonderful and just hope to return.

Responds fast! avg. 6 minutes

Price per night from

$59

Casa Cappuccini, Lago Trasimeno, Perugia, Umbria

Passignano Sul Trasimeno house

2 bedrooms / 1 bathroom / sleeps 5

“very peaceful, amazing view” We stayed for a month in this property and used it as our base to explore Umbria and Tuscany. It is a very beautiful area, and the property has amazing panoramic view of the Trasimeno lake. The property is been renovated, we stayed at the finished 2 bedroom apartment and waking up every morning and simply looking out the window on the lake, starts your day with happiness. All in all a very good stay, I recommended to the owner to add a washing machine, otherwise going to a laundromat is time consuming, boring and expensive.

Price per night from

$115

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

Price per night from

$154

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

Price per night from

$134

Borgo dei Sette Tigli #4

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect!” We had a 4-night stay here in early July of this year and had such a wonderful experience. We were greeted by alice who was very accommodating and patient even though we lost our way and were an hour late arriving. She was a sweet as can be and made sure we were settled and had all our questions answered before leaving. Barbara (the owner, I believe) came by the next day to greet us and was also wonderful, making sure that we were satisfied. She was taking care of details regarding her forthcoming nuptials which were to take place 5 days after our arrival. She was very accommodating and helpful even though she must have had lots on her mind. We rented a 2-bedroom, 2-bathroom apartment with a fully-equipped kitchen, living room/dining room, small walkout with table and chairs off of the kitchen. This was perfect for our family of 4 -- two adults and two teenage girls. The accommodations are superb: comfortable beds with great quality linens; recently and tastefully renovated rooms, spacious and inviting, fully equipped kitchen with dish washer and clothes washer; clothes are a quick dry in the summer sun on a dryer rack that is provided. The exterior of the buildings are very attractive, landscaping is detailed and well tended and there is a beautiful, beautiful pool. Now picture this in the middle of the lovely landscape of the Tuscany region. Need I say more? If you're thinking of staying here, don't hesitate, it is superb. Ideally located close to Montepulciano (5 minutes by car) and not far from the major highway (15 minutes tops) if you feel that you'll be doing some day trips. Exceptional value for the money. I highly recommend this vacation rental and only wish I could go back. Hopefully some day.

Price per night from

$206

Tigli #3, 2 bedrooms and 2 bathrooms apt close Montepulciano. Wi-Fi, A/C & pool!

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent apartments in a gorgeous location” I stayed with my family and another family for a week in apartments #1 and #3. The couple managing the compound are very nice and helpful, but also very strict and professional about the rules concerning payment, signing the lease agreement, etc. Expect to do a lot of paperwork and sign away all your rights to anything at all as part of the check-in process. But once that is done, they do their best to make your stay comfortable and pleasant. The good: the apartments are spacious and extremely well equipped, very comfortable. We were able to cook lunches and dinners for 9 people in the kitchen of our apartment (#1), comfortably; and we also were able to fit ourselves around both the indoor table and the outdoor patio table. There is a dishwasher and washing machine in each apartment, which is great. The bad: in aug. 2011, at least, internet by wifi was shaky at best, and in general almost impossible in #1. In #3 it was better. The problem is that the setup had a central wifi router someplace in the compound, and then repeater/extender routers in each apartment; but the thick stone walls of the buildings makes the connection weak and unreliable. Since you pay extra for the wifi, it's extra annoying when it doesn't work. Perhaps the owners have fixed this by now. The ugly: As far as I can tell, nothing in the Montepulciano region is ugly. The surroundings could hardly be more beautiful and perfect for a relaxing summer holiday.

Price per night from

$206

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

“Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Quiet, comfortable with a very suitable kitchen facilities, all helping to make a very relaxing home base in the middle of the wine area. A good map and GPS navigation system is a must to find your way in this amazing countryside.

Price per night from

$134

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

Price per night from

$154

I Casali di Colle S. Paolo-Garden apt., 2-bedrooms

Tavernelle di Panicale villa

2 bedrooms / 2 bathrooms / sleeps 6

“green outdoors plus charm at home” I stayed in the "Fontanelle" farmhouse of Colle San Paolo for 2 weeks in July, with an extended family of ten adults and 5 children- and we had an excellent stay and wondeful time-- the check-in, introduction to the rooms, and overall responsiveness was warm and excellent. The home is furnished beautifully and charmingly comfortable, with spectacular views particularly on the east and southern sides. All the amenities are excellent, including the common areas: the infinity swimming pool with beautiful view of the valley, patio/garden with lavender and ancient olive tree, shaded barbecue area and the common (games/eating) room- as well as of course the pristine woods around the farmhouse. We received excellent tips on where to go for wine-tasting; medieval villages (where we met a jolly band of Franciscan faithful walking for peace); donkey walks for the children; jazz music in medieval castles; and hidden monastries off the tourist map. Most of all we enjoyed the fresh air, beautiful views and relaxed setting at the swimming pool with lots of space for meals in the common room and nearby walks in the early evening. We enjoyed every minute, emersed in the Italian countryside, with lots to do nearby whenever we felt the impulse to leave this comfortable and charming home.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$188

Apartment Box Lucignano

Lucignano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$88

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$435

Large Studio apartment in Historical Centre - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$91

Big & Bright Studio in Tuscany near Cortona - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$71

I Casali di Colle S. Paolo-Villa, pool,3 bedrooms.

Tavernelle di Panicale villa

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 28 minutes

Price per night from

$317

Villa Le Crete, private house with 2 bedrooms. Pool and WiFi in the Val d'Orcia!

Castelmuzio villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

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