Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Ossaia vacation rentals

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, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ￥39,474
￥44,161 total
includes taxes & fees
May 13 - May 14
Castello di Gargonza
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 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
The price is ￥19,617
￥21,948 total
includes taxes & fees
May 12 - May 13
La Piccola Locanda
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥25,795
￥28,929 total
includes taxes & fees
May 12 - May 13
Abbadia Sicille Relais
Exterior

Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is ￥44,877
￥45,616 total
includes taxes & fees
May 12 - May 13
Oasi del Borgo Montefollonico
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (94 reviews)
"An amazingly beautiful and historic property. Our room had an incredible view. The staff was fantastic- welcoming and helpful. The location is spectacular. I highly recommend. "
United States
Hallie
The price is ￥25,791
￥29,109 total
includes taxes & fees
May 14 - May 15
Meublé Il Riccio
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ￥18,063
￥20,608 total
includes taxes & fees
May 12 - May 13
Bed & Breakfast Vicolo dell'Oste
Property grounds

Charlie's Home B&B-Private Parking-Arezzo Trade Fairs and Congresses-Historic Center

Charlie's Home B&B-Private Parking-Arezzo Trade Fairs and Congresses-Historic Center
Arezzo
The price is ￥147,742
￥162,701 total
includes taxes & fees
May 12 - May 13
Charlie's Home B&B-Private Parking-Arezzo Trade Fairs and Congresses-Historic Center
BBQ/picnic area

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
The price is ￥21,825
￥24,008 total
includes taxes & fees
May 20 - May 21
Residenza d'epoca Ca' de Principi
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (100 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is ￥14,203
￥16,363 total
includes taxes & fees
May 13 - May 14
Residenza Fabroni
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (138 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is ￥28,514
￥32,104 total
includes taxes & fees
Jun 11 - Jun 12
La Locanda di San Francesco
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥15,290
￥17,927 total
includes taxes & fees
May 18 - May 19
iConic Wellness Resort
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 ￥21,316
￥24,186 total
includes taxes & fees
May 18 - May 19
San Michele al Borgo
Exterior

Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!

Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!
Chianciano Terme
9.4 out of 10, Exceptional, (10 reviews)
"This is a marvelous property and the owners Fulvia and Umberto couldn't be more welcoming, helpful and sincerely nice people. I wish we could have stayed longer and would highly recommend this place to anyone who wants to stay in Tuscany. It was the highlight of our trip."
United States
Diane D.
The price is ￥73,871
￥98,802 total
includes taxes & fees
May 14 - May 15
Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!
Exterior detail

Apartment with pool in Montepulciano

Apartment with pool in Montepulciano
Montepulciano
The price is ￥88,645
￥88,645 total
includes taxes & fees
May 30 - May 31
Apartment with pool in Montepulciano
Exterior

Mivà di Più Vacation Rental: 1 Bedroom House

Mivà di Più Vacation Rental: 1 Bedroom House
Arezzo
The price is ￥184,492
￥195,203 total
includes taxes & fees
May 12 - May 13
Mivà di Più Vacation Rental: 1 Bedroom House
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 ￥22,468
￥25,084 total
includes taxes & fees
May 13 - May 14
Borgo Dolciano
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is ￥44,499
￥49,318 total
includes taxes & fees
May 12 - May 13
Fontelunga Hotel & Villas
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is ￥31,277
￥35,144 total
includes taxes & fees
May 18 - May 19
Delcorto Suites
Fridge, microwave, oven, stovetop

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is ￥155,400
￥155,400 total
includes taxes & fees
May 12 - May 13
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
Interior

Boutique Apartment Family

Boutique Apartment Family
Chiusi
The price is ￥17,179
￥20,957 total
includes taxes & fees
May 17 - May 18
Boutique Apartment Family
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

8/10 Good
"Good hotel, the only problem for us was that the food menu is very limited, the kitchen is closed most of the time and in La Toscana there is no life outside the hotel, so If the kitchen is closed there is no delivery service or restaurants around."
MELISSA 4-night trip
Posted 2 days ago
Precise Tale Poggio Alla Sala

Find out more about Ossaia

Search for holiday rentals in Ossaia on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossaia using one of the methods below:

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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.

What are some of the best vacation home rentals in Ossaia?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental near Ossaia is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Ossaia?

With 6 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 Isola Maggiore. 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.