Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Ossaia vacation rentals

Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
Luxury resort in the Tuscan countryside
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (133 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is P10,017
P11,294 total
includes taxes & fees
Mar 4 - Mar 5
La Locanda di San Francesco
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (168 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P4,835
P5,525 total
includes taxes & fees
Feb 26 - Feb 27
Abbadia Sicille Relais
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
Castello di Gargonza
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is P3,674
P4,041 total
includes taxes & fees
Feb 22 - Feb 23
L'Antica Sosta
Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful "
United States
Rocio Q
The price is P10,689
P12,033 total
includes taxes & fees
Feb 19 - Feb 20
Delcorto Suites
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (87 reviews)
"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."
United States
Michael.
Meublé Il Riccio
Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is P4,847
P5,607 total
includes taxes & fees
Feb 19 - Feb 20
Residenza Fabroni
Exterior

Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is P8,531
P9,522 total
includes taxes & fees
Feb 18 - Feb 19
Borgo Dolciano
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Exterior

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is P7,059
P8,040 total
includes taxes & fees
Feb 18 - Feb 19
San Michele al Borgo
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is P4,985
P5,621 total
includes taxes & fees
Feb 18 - Feb 19
Artisti del Cavallo Tourism
Breakfast area

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is P7,059
P7,765 total
includes taxes & fees
Feb 27 - Feb 28
Locanda Antico Borgo
Interior entrance

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very Good, (4 reviews)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole
Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is P6,855
P7,678 total
includes taxes & fees
Feb 19 - Feb 20
Vicolo Della Scala Rooms - Il Sole
2 bedrooms, desk

Mery s House Elegant Apartment

Mery s House Elegant Apartment
Montepulciano
The price is P17,899
P28,524 total
includes taxes & fees
Mar 1 - Mar 2
Mery s House Elegant Apartment
View from room

B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very Good, (74 reviews)
"Stayed in the top floor room with the terrace and seating area. Definitely a great decision. Arrezo was the starting point of our Tuscany tour and glad we spent an extra night and day. Great room super convenient to town and the train station. "
United States
Edward
The price is P4,507
P5,372 total
includes taxes & fees
Feb 19 - Feb 20
B&B 52cento
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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Top Ossaia Hotel Reviews

Albergo San Biagio

Albergo San Biagio

10/10 Excellent
"Muy amable "
Arturo 3-night trip
Posted 3 weeks ago
Albergo San Biagio

Find out more about Ossaia

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Frequently asked questions

Are there vacation rentals in Ossaia?

Yes, you can find vacation rentals near top local attractions in Ossaia, or you can select a more remote option if you're looking for a relaxing stay.

How many vacation rentals are there in Ossaia?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Ossaia stay.

What’s there to see and do in Ossaia?

While exploring the area, visit family-friendly sights like Naturalistic Oasis La Valle, or get outside and enjoy nature at Hannibal's Journey. In the larger area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a vacation rental in Ossaia like?

Vacation rentals are private properties where you can stay for a couple of days or more in Ossaia. Vacation rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.