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Compare 1100 Vacation Homes in Ossaia with updated reviews, rates, and availability.

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

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

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

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

Stone house - charming country villa in Tuscany

Stone house - charming country villa in Tuscany

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.

Beautiful Residence in the Old Town

10.0 out of 10, Exceptional, (44)
"Perfect location to explore the surrounding area and the town—close to shopping and restaurants. Royce was a very helpful and gracious host. One alert: the apt rooms are on separate levels so be prepared for a few to several stairs between levels."
Beautiful Residence in the Old Town

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

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace

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

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

Lake Trasimeno San Savino Townhouse AC Free WI-FI

10.0 out of 10, Exceptional, (57)
"An absolutely beautiful house. The interior is completely modern. The house is very well appointed. The village is a dream. David is suoer nice and helpful. There are some steep steps if you have mobility issues. Currently you cant really use the lake beaches because the water is too low. We did rent a motor boat which was an excellent way to experience the lake. "
Lake Trasimeno San Savino Townhouse AC Free WI-FI

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

La Dolce Collina

Belvilla by OYO Fienile

Belvilla by OYO Fienile

Belvilla by OYO Elegant Flat in Historic Villa

Belvilla by OYO Elegant Flat in Historic Villa

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

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

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

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
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

4.0 star property
8.8 out of 10, Excellent, (157)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is SAR 318
SAR 362 total
includes taxes & fees
27 Mar - 28 Mar
Abbadia Sicille Relais

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 964
SAR 1,076 total
includes taxes & fees
27 Mar - 28 Mar
Il Tosco

Residenza Fabroni

8.8 out of 10, Excellent, (82)
"This is a very large apartment in a 500 year old well maintained building. It is in the beautiful historic area. Do be aware that this is a VERY hilly area and you will have to walk up and down steep streets everywhere you go. That includes from the parking area. Cars are restricted from the area around the apartment without a permit. "
The price is SAR 310
SAR 357 total
includes taxes & fees
31 Mar - 1 Apr
Residenza Fabroni
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.