Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Ossaia vacation rentals

Free daily buffet breakfast

Relais La Saracina

Relais La Saracina
Pienza
The price is ￥52,462
￥58,445 total
includes taxes & fees
Mar 28 - Mar 29
Relais La Saracina
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is ￥32,626
￥36,442 total
includes taxes & fees
Mar 30 - Mar 31
Luxury resort in the Tuscan countryside
Panoramic Cottage, 1 Bedroom | 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
The price is ￥16,436
￥22,668 total
includes taxes & fees
Mar 30 - Mar 31
Affitacamere Maria Gabriella
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
The price is ￥18,204
￥20,394 total
includes taxes & fees
Mar 27 - Mar 28
La Piccola Locanda
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (169 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥11,668
￥13,388 total
includes taxes & fees
Mar 31 - Apr 1
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, (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 ￥37,000
￥41,437 total
includes taxes & fees
Apr 4 - Apr 5
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 ￥9,850
￥10,835 total
includes taxes & fees
Mar 29 - Mar 30
L'Antica Sosta
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 ￥24,626
￥27,826 total
includes taxes & fees
Apr 21 - Apr 22
La Locanda di San Francesco
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (90 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is ￥26,258
￥29,621 total
includes taxes & fees
Mar 27 - Mar 28
Meublé Il Riccio
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 ￥12,998
￥15,035 total
includes taxes & fees
Apr 9 - Apr 10
Residenza Fabroni
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (129 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ￥14,981
￥17,216 total
includes taxes & fees
Mar 30 - Mar 31
Bed & Breakfast Vicolo dell'Oste
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 ￥18,550
￥20,405 total
includes taxes & fees
Mar 27 - Mar 28
Locanda Antico Borgo
Fridge, microwave, oven, stovetop

Mery's House- elegant apartment

Mery's House- elegant apartment
Toscana
10.0 out of 10, Exceptional, (1 review)
"Our accommodations in montepulciano was as wonderful as the area’s scenery. The place was clean, spacious and conveniently located to the old town for our party of four and Mery, our host, provided everything we could possibly need during our two night stay. She even offered to pick us up at the bus station when we arrived. We wished we could have stayed longer to enjoy our lodging and montepulciano’s charms."
United States
YenMing C.
The price is ￥48,093
￥54,174 total
includes taxes & fees
Mar 27 - Mar 28
Mery's House- elegant apartment
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 ￥46,323
￥51,324 total
includes taxes & fees
Apr 6 - Apr 7
Fontelunga Hotel & Villas
Outdoor pool

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (8 reviews)
"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."
United States
cinzia c.
The price is ￥17,911
￥30,625 total
includes taxes & fees
Mar 27 - Mar 28
Villa Graziella, Romantic Perugia
Property grounds

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is ￥24,845
￥28,715 total
includes taxes & fees
Mar 28 - Mar 29
Il Poggio dell'Eremita
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 ￥28,244
￥31,806 total
includes taxes & fees
Mar 28 - Mar 29
Delcorto Suites
Exterior

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is ￥33,168
￥45,882 total
includes taxes & fees
Apr 1 - Apr 2
Eagle House
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 ￥12,212
￥14,539 total
includes taxes & fees
Apr 19 - Apr 20
iConic Wellness Resort
Interior

Boutique Apartment Family

Boutique Apartment Family
Chiusi
The price is ￥14,491
￥17,679 total
includes taxes & fees
Mar 31 - Apr 1
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

Palazzo Mosela Alla Porta

Palazzo Mosela Alla Porta

10/10 Excellent
"Everything was amazing. Bruno made it so easy for us to get to our room, check in, know where to eat, and even made reservations for us. He is truly an outstanding host and the room and building are gorgeous. The view from our balcony was to die for. What a delight."
Alexis 1-night trip
Posted 13 days ago
Palazzo Mosela Alla Porta

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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This vacation home rental near Ossaia is located in a rural location and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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 Isola Maggiore. In the larger area, you’ll find Giuseppe Garibaldi Memorial and Villa Bramasole.

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.