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Compare 1333 Villas in Ossaia with updated reviews, rates, and availability.

Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Pool
Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
9.8 out of 10, Exceptional, (29)
"We are traveling with 6 persons through Italy. This villa was a wonderful change of pace to the crowded streets of the cities. Beauty, clean, and well stocked. A little off the grid but worth the train rides and car rental. "
Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Idyllic Tuscan Farmhouse Near Cortona, Italy With Private Pool & Wifi
1 acre of fenced gardens
Idyllic Tuscan Farmhouse Near Cortona, Italy With Private Pool & Wifi
10.0 out of 10, Exceptional, (31)
"The villa was exceptional, and the owners provided a very comprehensive guide to the area, places to visit, restaurant recommendations, road trips which significantly enhanced the holiday with local knowledge. The owners also provided us with a customised list of running routes knowing my wife is a keen runner - they couldn't have been more helpful. The villa is adjacent to a small vinyard run by a friendly family - they made us feel very welcome to the area and arranged an impromptu...
Idyllic Tuscan Farmhouse Near Cortona, Italy With Private Pool & Wifi
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (45)
"It's hard to imagine what could have been better. The villa is stunning. On a hilltop will amazing views. Well appointed and with 12 rooms, all with ensuites. A large kitchen and dining space and loads more outside space than the pictures really show. Morning coffee on the lower sun terrace, the afternoon spent by the pool, the evening in the jacuzzi, and then wine (SO MUCH WINE) from the provided supplies to talk as the night grew around us. Not to mention the small gym, or table...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Cortona Umbria / family lake view villa near Tuscany + large salted pool
Interior
Cortona Umbria / family lake view villa near Tuscany + large salted pool
10.0 out of 10, Exceptional, (91)
"Great place to stay, but for us, we were out exploring surrounding area most of the day. The villa is up a rough road, so you won’t want to go up/down too much. Pool is not used after summer. "
Cortona Umbria / family lake view villa near Tuscany + large salted pool
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Pool, house, & garden with Tuscan farms below & medieval town of Cortona.
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
10.0 out of 10, Exceptional, (46)
"This property is all it explains to be. The stay included myself, my husband, my daughters and their families. The property is spectacular, the rooms as beautiful as shown. The guesthouse was perfect for my daughter, her husband and 2 young children. The travel cots were perfect and opening the chest of toys brought so much joy to my 2 year old granddaughter. We utilized the kitchen and pizza oven and have such wonderful memories to hold. Our only disappointment was that the pool heater was not...
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Charming Villa with private pool <br>Villaventotto
Exterior
Charming Villa with private pool <br>Villaventotto
9.8 out of 10, Exceptional, (16)
"We had a great time. We stayed for two days"
The price is SAR 1,310
SAR 2,005 total
includes taxes & fees
1 Dec - 2 Dec
Charming Villa with private pool <br>Villaventotto
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
Garden, Outdoor, Pool
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
10.0 out of 10, Exceptional, (61)
"This house is not a "normal" house but with a lot of different rooms. Filled with nice arts and decorated with some old furniture. Real characteristic Italian house. Nice garden with different places to seat. The only comment what I can give is the small kitchen. The garden and the swimming pool is maintained daily. We stayed here with 6 adults ad 4 children. Nice place to be."
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"
Pool
Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"
9.8 out of 10, Exceptional, (26)
"What an awesome property! Our host was not only knowledgeable of area but was an excellent chef! The villa exceeded all our expectations. It is strategically located to visit towns and historical sites! A must stay!"
Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Villa Miralaghi from the private heated swimming pool 5x8 1,40 constant depth.
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
9.4 out of 10, Exceptional, (41)
"Our group of five women thoroughly enjoyed our two-week stay at Miralaghi. We were in the main house (old hunting lodge) with 4-bedrooms, 3 baths, huge living space, kitchen, carport, and private pool. Miralaghi is a unique property, located between Paciano and Moiano, high up on a hillside. It is very peaceful, quiet and provides lovely hiking trails on the huge, 750 acre property. It's a perfect retreat at the end of a day of visiting nearby hill towns. Our host, Mausi, was a delight and so...
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
10.0 out of 10, Exceptional, (1)
"Bellissimo casolare ben tenuto con magnifico giardino e grande piscina. La padrona di casa gentilissima e molto discreta. Abbiamo soggiornato in agosto con amici e ci siamo trovati benissimo. Assolutamente consigliato!"
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Panoramic View Village of Villa Luigina Cortona
Terrace/patio
Panoramic View Village of Villa Luigina Cortona
Panoramic View Village of Villa Luigina Cortona
Beautiful Villa in a peaceful place, ideal for family holidays.
Pool
Beautiful Villa in a peaceful place, ideal for family holidays.
10.0 out of 10, Exceptional, (7)
"This is our second visit to Annie's beautiful farmhouse and we hope to visit again next year. It's an incredibly special place - perfectly peaceful, thoughtfully and generously furnished and child friendly. Selfishly we hope the house doesn't become too popular! Thanks again Annie for letting us stay."
Beautiful Villa in a peaceful place, ideal for family holidays.
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Exterior
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
10.0 out of 10, Exceptional, (2)
"Such a quaint home, clean, quiet and beautiful. Close to the center of the very small town of Montepulciano. The host is very sweet and even cooked a cake to welcome us to their home. The view of the valley from the home is simply breathtaking."
The price is SAR 1,786
SAR 2,124 total
includes taxes & fees
15 Nov - 16 Nov
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Vrbo Property
Pool
Vrbo Property
10.0 out of 10, Exceptional, (3)
"A wonderful Umbrian property with spectacular views over the lake. Paola was really helpful and we had a couple of great trips to recommended restaurants. Great relaxing view"
Vrbo Property
House with garden and panoramic view over Lake Trasimeno
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (43)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno
Big house
Overview
Big house
7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Villa Scopetello
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
View from pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (62)
"This house and adjacent apartment was perfect for a larger group. The rooms are comfortable and well equipped. The property was lovely and has a spectacular pool. A few things to note. The house name is not a location on a map and if you use an app like Google then you must use the name on the wall outside the property. The hot water takes a very long time to get to the upper floor shower and it’s almost impossible to fill a hot bath. That’s to be expected in a house of this age and it’s well...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Il Poggio dell'Eremita
Exterior
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is SAR 584
SAR 675 total
includes taxes & fees
15 Nov - 16 Nov
Il Poggio dell'Eremita
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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Other property types in Ossaia

Abbadia Sicille Relais
Property entrance
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (152)
"Beyond the peace and tranquility offered by the setting, it truly felt like the guests’ wellbeing was prioritized- the spaces (I viewed three before making a decision) were clean and orderly, the staff was incredibly attentive, the restaurant was enjoyable, and the overall experience was a very positive one."
The price is SAR 214
SAR 246 total
includes taxes & fees
25 Nov - 26 Nov
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, (110)
"Wonderful location in Arezzo. The home itself is Amazing, Beautiful, Historic yet with Modern conveniences. Stefano, your host is so accommodating, incredibly helpful and is sure to make your stay perfect. If we could give it more ⭐️ stars we would!!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
House with garden and panoramic view over Lake Trasimeno
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (43)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno
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.