Search Vacation Homes in Ossaia

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 948 Vacation Homes in Ossaia with updated reviews, rates, and availability.

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
House / Villa - Monte San Savino
Property grounds

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
Podere Casorbica with free parking, large garden, swimming pool.
Pool

Podere Casorbica with free parking, large garden, swimming 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, swimming pool.
houses / villas - 6 rooms - 7/11 persons
Facade

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
Agriturismo Nestore
Outdoor pool

Agriturismo Nestore

10.0 out of 10, Exceptional, (4)
"Ottima struttura, facilmente raggiungibile. Pulita. Personale molto cordiale. "
Agriturismo Nestore
A MAGICAL HOLIDAY IN TUSCANY
Living area

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
La Dolce Collina
Outdoor pool

La Dolce Collina

La Dolce Collina
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
Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city
Pool

Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city

10.0 out of 10, Exceptional, (25)
"What a wonderful location , peaceful and relaxing Fabio and Loretta were amazing hosts we felt like family . They were available at all times to help us navigate our needs. Their recommendations were exactly what we wanted , fabulous dinners and wine . Their home was inviting well stocked and the views were beautiful. We took a stroll through the neighborhood that left us feeling like we had stepped into a fairy tale. It met our expectations and more ! Can not wait to visit again ! Thank you...
Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city
Belvilla by OYO Fienile
Holiday Home Swimming Pool

Belvilla by OYO Fienile

Belvilla by OYO Fienile
Belvilla by OYO Casa Tommaso - Bilo 1 P - 4 pax
View from property

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
beautiful tuscan villa with pool, ideal for groups
Exterior

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
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
Swimming 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
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Exterior

Villa Banditello, secluded, panoramic view over Montepulciano valley.

10.0 out of 10, Exceptional, (23)
"This property and our stay was outstanding. Everything was exactly as we hoped. We had an absolutely wonderful stay. The villa is away from the city, but the town is easily accessible. You do need a car. The view from the property is like in a dream and we sat for many hours in the mornings and evenings taking it in. The home is spotless with everything we could possibly need. The owner is extremely helpful and assisted us with dinner reservations and our many questions. We even had wood...
Villa Banditello, secluded, panoramic view over Montepulciano valley.
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
Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!
Interior

Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!

Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!
Casa Fontelunga, Tuscan holiday villa with private pool
Interior

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
Experience Tuscany at its best in this charming pool holiday home.
pool

Experience Tuscany at its best in this charming pool holiday home.

Experience Tuscany at its best in this charming pool holiday home.
Stone house - charming country villa in Tuscany
Room

Stone house - charming country villa in Tuscany

Stone house - charming country villa in Tuscany
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.
Don't see what you're looking for?
See all available properties in Ossaia
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Ossaia

Wonderful villa at the foot of Cortona with private pool and unforgettable views
Pool

Wonderful villa at the foot of Cortona with private pool and unforgettable views

10.0 out of 10, Exceptional, (2)
"I want to move into this villa. It was amazing from start to finish with only one or two minor issues. The location was perfect for visiting nearby towns and wineries. The American style coffee maker was ancient and it took over an hour to brew a cup of coffee. Once we cleaned it with vinegar it worked a lot better. Sadly we did not use the pool due to the weather. I definitely would return to this villa. "
Wonderful villa at the foot of Cortona with private pool and unforgettable views
Abbadia Sicille Relais
Front of property - evening/night

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (155)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is SAR 257
SAR 295 total
includes taxes & fees
19 Feb - 20 Feb
Abbadia Sicille Relais
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Interior

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

10.0 out of 10, Exceptional, (112)
"We were in awe! So beautiful, comfortable and peaceful. Best sleep ever on vacation. Stefano is an amazing host, very responsive and helpful. Great recommendations and knowledge of area made our visit even more special. Location is walking distance to the Grande Piazza, restaurants, groceries and a lovely bakery right across the street. His dog, Spritz will steal your heart. I could go on and on…..see other reviews, you will not be disappointed. We did not want to leave! I highly...
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
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.