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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 1103 Vacation Homes in Monsigliolo with updated reviews, rates, and availability.

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Interior

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

9.8 out of 10, Exceptional, (66)
"The views from this house are fantastic! And the location is perfect - steps from the old town of Montepulciano. Communication with Erika, the host was great. She prepared us with lots of details and recommendations for things to do nearby. We had some questions during our stay and Erika was very responsive. There is so much to do in the area - I almost wished we had more time to hang out on the beautiful terraces!"
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Beautiful home in Sarteano with WiFi
Pool

Beautiful home in Sarteano with WiFi

10.0 out of 10, Exceptional, (1)
"So schön, dass wir nächstes Jahr wiederkommen. Haben direkt wieder gebucht. Tolle herzliche Gastgeber und eine wunderschöne Umgeht"
Beautiful home in Sarteano with WiFi
Casa Fontelunga, Tuscan holiday villa with private pool
Outdoor pool

Casa Fontelunga, Tuscan holiday villa with private pool

9.4 out of 10, Exceptional, (8)
"Very thoughtfully restored old Villa just minutes from Cortona . The house and grounds are exactly as pictured. The very private road that leads there is a bit rough and seems very remote at first but after you venture out once you see that every convenience is minuets away and beautiful Cortona as well. A car is a good idea if you plan to go around Tuscany. 2 trains in town go everywhere but it helps to get to train and town with a car. The host is very responsive and hands on."
Casa Fontelunga, Tuscan holiday villa with private pool
Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany
Outdoor pool

Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany

10.0 out of 10, Exceptional, (14)
"We enjoyed our first visit here we chose to return for our honeymoon. Lorella and her family are so warm and lovely, very welcoming and happy to offer advice about the property and surrounding area. The villa itself is beautiful. Sat on a small promontory on a larger hill/ridge, it has stunning views down and along a gorgeous valley. The pool is very large and very private - offering long days of catching sun and cooling off in the water. The kitchen is easy to use if you prefer self...
Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany
Podere Casorbica with free parking, large garden, private pool.
Exterior

Podere Casorbica with free parking, large garden, private pool.

9.4 out of 10, Exceptional, (13)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, private pool.
Stone house - charming country villa in Tuscany
Terrace/patio

Stone house - charming country villa in Tuscany

Stone house - charming country villa in Tuscany
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Outdoor dining

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

9.8 out of 10, Exceptional, (8)
"Casa Delle Rosa had everything we needed and was very well equipped but the view… amazing. We were able to walk everywhere in Cortona and hope to return during warmer weather. Thank you Isabella and the team at Together in Tuscany for making it a seamlessly easy stay"
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
A MAGICAL HOLIDAY IN TUSCANY
4 bedrooms, desk, iron/ironing board, travel crib

A MAGICAL HOLIDAY IN TUSCANY

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay for 2 nights. Perfectly located in the heart of the town. Comfortable rooms of lots of space. "
A MAGICAL HOLIDAY IN TUSCANY
houses / villas - 6 rooms - 7/11 persons
Pool

houses / villas - 6 rooms - 7/11 persons

9.8 out of 10, Exceptional, (44)
"A lovely property, with lots of charm. We had a great stay and the hosts were very helpful. "
houses / villas - 6 rooms - 7/11 persons
Olimpia by Interhome
Outdoor dining

Olimpia by Interhome

9.0 out of 10, Wonderful, (14)
"Schön eingerichtetes Häuschen mit toller Aussicht. Der Garten ist mit viel Liebe zum Detail hergerichtet mit immer wieder kleinen Sitzgruppen umgeben von Grün. Der Pool ist eine Wucht, hat uns riesigen Spaß bereitet und ist der absolute Blickfang des umzäunten Geländes. Das Ferienhaus ist gut gelegen und man kann sehr schnell tolle Ausflugsziele wie Chiusi und Castiglione del Lago (mit Auto beides ca. 20Min), wie auch Perugia (ca. 50Min) erreichen. Wir haben das Haus, den Pool und die tolle...
Olimpia by Interhome
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
Pool

La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

7.4 out of 10, Good, (3)
"Un luogo che ha lasciato tutti noi (sia adulti che bambini) a bocca aperta: un paradiso terrestre! Per chi ama la natura, vuole staccare dalla caotica vita quotidiana e godere del tempo con i propri cari , questo è il posto che offre tutto ciò e di più! Non conoscendo bene la zona siamo arrivati un po’ impreparati ma tutto si è risolto con un viaggio al supermercato vicino Cortona! *essendo immersi nella natura c’è’ da far conto di insetti e possibili cervi e cinghiali, che rendono questo posto...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
La Dolce Collina
Aerial view

La Dolce Collina

La Dolce Collina
Belvilla by OYO Fienile
Pool

Belvilla by OYO Fienile

Belvilla by OYO Fienile
Belvilla by OYO Casa Tommaso - Bilo 1 P - 4 pax
Apartment | Pool | Outdoor pool

Belvilla by OYO Casa Tommaso - Bilo 1 P - 4 pax

Belvilla by OYO Casa Tommaso - Bilo 1 P - 4 pax
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (67)
"Was wonderful and beautiful. "
Farmhouse in the hills with panoramic view and swimming pool
House / Villa - Monte San Savino
Terrace/patio

House / Villa - Monte San Savino

9.8 out of 10, Exceptional, (16)
"Es erwartet dich ein hübsches Häuschen mitten in der Natur. Etwas abgelegen, wir mochten es genau so. Natur und Ruhe pur. Die Inneneinrichtung ist schon etwas in die Jahre gekommen, aber es ist alles da was man braucht. "
House / Villa - Monte San Savino
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
Pool

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

8.2 out of 10, Very Good, (42)
"We had a great stay at Massimo place. The grounds and pool were great! The views were to die for, and we had a different sun set every night! Thanks for the great stay Massimo! Will definitely back if in the area."
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (4)
"Our two adult children who were studying abroad met us here with our younger two children. We had two nights in a 12 day stay in Italy. Of all our stops, this was by far our favorite. The house was like a story book. The garden was so lovely, we spent an afternoon eating and sharing a bottle of wine. We were here in November and the weather was very mild compared to Chicago winters. Most of the stores and restaurants were open with far less people. We weren’t really here to see anything, we were...
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Outdoor dining

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

9.8 out of 10, Exceptional, (55)
"H"
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
beautiful tuscan villa with pool, ideal for groups
Terrace/patio

beautiful tuscan villa with pool, ideal for groups

10.0 out of 10, Exceptional, (25)
"A wonderful property, submerged in beautiful natural surroundings, the flora and fauna were fantastic. Our whole family were delighted by the swifts, starlings and kestrels nesting at the property, my parents described the place as simply magical. Wonderful location for my Father's 80th birthday celebrations, John and Sabine are welcoming and warm hosts. We all felt very relaxed in this comfortable, spacious home. The outside is as well equipped as inside with lots of seating and a great pool...
beautiful tuscan villa with pool, ideal for groups
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 Monsigliolo

Hotel San Gregorio
Seasonal outdoor pool, sun loungers

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (111)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 447
SAR 516 total
includes taxes & fees
30 Mar - 31 Mar
Hotel San Gregorio
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Outdoor pool

Traditional stone cottage in rural, tranquil and quiet location built in 1799

9.8 out of 10, Exceptional, (39)
"John & Dianne were utterly lovely and made every effort for us. The listing is very clear and if you're looking for peace and quiet in a serene valley, you couldn't do better. The track should be driven with care but after the first time accompanied by John, it's not too bad. I wouldn't bring a car with low clearance though. John and Dianne are in their home next door which was nice to know. They very much left us to it and didn't mind us playing our music by the pool. Otherwise we didn't see...
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Abbadia Sicille Relais
View from room

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (158)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is SAR 442
SAR 498 total
includes taxes & fees
9 Apr - 10 Apr
Abbadia Sicille Relais
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.