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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 1100 Vacation Homes in Ossaia 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)
"This is a beautiful property and we really enjoyed our stay. Thank you to the host family for making us feel welcomed."
Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany
detached villa with a private swimming pool and a large terrain
Pool

detached villa with a private swimming pool and a large terrain

10.0 out of 10, Exceptional, (48)
"We had a lovely stay at Daniela’s property in Umbria. The house was clean and very well maintained, with a great private pool and garden. It was a quiet and secluded spot, with an amazing view. Communication with the host was easy and we felt very welcome at the property. Would highly recommend."
detached villa with a private swimming pool and a large terrain
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)
"We travelled to Italy for 2 weeks and visited Venice, Florence, Cortona and Rome. Our most favorite stay was without a doubt was this home in Cortona. It was exactly as described and we loved the location. Only downside is parking. If you have a car, you will be lugging your luggage uphill for a good ways from the parking area. "
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"
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 Ossaia

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 398
SAR 450 total
includes taxes & fees
3 Apr - 4 Apr
Abbadia Sicille Relais
Residenza Fabroni
Lobby

Residenza Fabroni

8.8 out of 10, Excellent, (82)
"We really enjoyed our stay in Residenza Fabroni. It was especially nice that we were given a free upgrade to the suite Rossa. A large room with an incredible view across the valley and also part of the town. The only thing is to be aware that there are 3+ flights of stairs and no elevator. "
The price is SAR 326
SAR 375 total
includes taxes & fees
4 Apr - 5 Apr
Residenza Fabroni
Il Tosco
Property entrance

Il Tosco

10.0 out of 10, Exceptional, (104)
"What a spectacular stay! My family chose this place as home base for our week in Tuscany and it’s literally one of the most incredible places we have ever stayed- the building has an amazing history- the rooms were beautiful and furniture stunning- lots of hot water- very clean- high quality linens etc The breakfasts prepared by the owner were over the top good- and she always lefts many cakes- desserts and snacks for my family - as well as fruit- treats and drinks - there are many restaurants...
The price is SAR 934
SAR 1,044 total
includes taxes & fees
6 Apr - 7 Apr
Il Tosco
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.