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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Ossaia vacation rentals

Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (144 reviews)
"Great location."
United States
James
The price is ￥21,882
￥24,805 total
includes taxes & fees
Jul 19 - Jul 20
La Locanda di San Francesco
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (111 reviews)
"It was very well located ."
Canada
Marlenne
The price is ￥26,175
￥29,528 total
includes taxes & fees
Jun 29 - Jun 30
Meublé Il Riccio
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, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥23,896
￥27,388 total
includes taxes & fees
Jul 19 - Jul 20
iConic Wellness Resort
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥24,842
￥27,877 total
includes taxes & fees
Jun 28 - Jun 29
Abbadia Sicille Relais
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (138 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is ￥19,876
￥22,598 total
includes taxes & fees
Jun 26 - Jun 27
Bed & Breakfast Vicolo dell'Oste
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 ￥21,708
￥23,879 total
includes taxes & fees
Jun 26 - Jun 27
Residenza d'epoca Ca' de Principi
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is ￥28,183
￥31,737 total
includes taxes & fees
Jun 27 - Jun 28
Delcorto Suites
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 ￥19,512
￥21,831 total
includes taxes & fees
Jun 26 - Jun 27
La Piccola Locanda
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ￥15,197
￥17,452 total
includes taxes & fees
Jul 8 - Jul 9
DormiVeglia B&B
Exterior

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 ￥18,492
￥20,341 total
includes taxes & fees
Jun 27 - Jun 28
Locanda Antico Borgo
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is ￥12,186
￥14,139 total
includes taxes & fees
Jun 30 - Jul 1
Residenza Fabroni
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥20,965
￥23,796 total
includes taxes & fees
Jun 29 - Jun 30
B&B Piccolo Hotel
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (189 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is ￥13,511
￥15,964 total
includes taxes & fees
Jul 12 - Jul 13
Cameracaffè Centro
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 ￥10,392
￥11,432 total
includes taxes & fees
Jul 3 - Jul 4
L'Antica Sosta
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very Good, (81 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is ￥13,237
￥15,662 total
includes taxes & fees
Jul 15 - Jul 16
B&B 52cento
Junior Suite | Terrace/patio

Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is ￥17,449
￥19,929 total
includes taxes & fees
Jun 26 - Jun 27
Casale dell'Assiolo
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 ￥28,605
￥31,832 total
includes taxes & fees
Jun 27 - Jun 28
Borgo Dolciano
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (125 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is ￥42,887
￥47,911 total
includes taxes & fees
Jun 30 - Jul 1
Il Tosco
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very Good, (17 reviews)
"To far out"
United States
Dennis
The price is ￥16,453
￥24,343 total
includes taxes & fees
Jul 5 - Jul 6
Castello di Modanella
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is ￥55,870
￥61,824 total
includes taxes & fees
Jul 7 - Jul 8
Fontelunga Hotel & Villas
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

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Our stay here was such a great and relaxing experience. From the moment we arrived, the staff were welcoming and very helpful. The location and the views are just stunning.. The resort is about a 10 minute walk to the lower part of Montepulicano. From the resort, there are amazing views of the top of Montepulciano, and the valley below. The room was very clean with all of the amenities that are expected. We spent time at the pool, which was very relaxing and refreshing. The staff serve food and drinks out to the pool. We also had the breakfast included in our stay. There are hot and cold options with the breakfast, including eggs, bacon, breads, pastries, fruit and veggies, and juices and fresh made coffee to order. To sum it up, our stay here was perfect. Thank you Nuovo Etruria for making our vacation truly relaxing and memorable."
Michael 1-night trip
Posted 2 hours ago
Nuovo Etruria Resort

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:

  • View our selection of featured holiday rentals in Ossaia
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Look no further and take a look at our great range of rental properties in Ossaia!

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?

Podere Casorbica with free parking, large garden, private pool.: This vacation home near Ossaia is located in a rural location and has an outdoor pool, a fireplace, 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. You can relax into your vacation with a balcony and a garden.

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 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.