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Check prices for these dates

Next weekend
30 May - 1 Jun
In two weeks
6 Jun - 8 Jun
In one month
20 Jun - 22 Jun
In two months
18 Jul - 20 Jul

Compare 1547 Villas in Ossaia with updated reviews, rates, and availability.

Villa with pool and garden
Pool

Villa with pool and garden

Villa with pool and garden
Stunning Villa, Private Swimming Pool, Breathtaking Views, BBQ, AC, Sleeps 10
Outdoor dining

Stunning Villa, Private Swimming Pool, Breathtaking Views, BBQ, AC, Sleeps 10

9.6 out of 10, Exceptional, (16)
"We had a lovely stay at this wonderful place with fabulous views and great pool. The fabulous view means you need to be comfortable to navigate some windy tracks and is more suited to a relaxing week than a hectic sightseeing schedule. "
Stunning Villa, Private Swimming Pool, Breathtaking Views, BBQ, AC, Sleeps 10
Winery Villa in the heart of Nobile Vineyards.
Interior

Winery Villa in the heart of Nobile Vineyards.

10.0 out of 10, Exceptional, (11)
"We love our stay. House and property are beautiful."
Winery Villa in the heart of Nobile Vineyards.
Il Poggio dell'Eremita
Terrace/patio

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (50)
"Our family of 4 had such a beautiful time at this gorgeous villa. We only stayed for 2 nights, wish we stayed longer. Highly recommend!"
The price is AED 537
AED 619 total
includes taxes & fees
22 May - 23 May
Il Poggio dell'Eremita
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Exterior

PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

10.0 out of 10, Exceptional, (197)
"The property was beautiful and well beyond our expectations! We were a group of friends and we all are looking forward to staying again! The team at the property were amazing! "
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Fridge, microwave, oven, stovetop

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (48)
"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Private Villa with WIFI, private pool, A/C, patio, panoramic view, parking, close to Montepulciano
Property grounds

Private Villa with WIFI, private pool, A/C, patio, panoramic view, parking, close to Montepulciano

8.2 out of 10, Very Good, (21)
"80 von 100 punkten. Ein sehr schönes Haus mit einem super Pool. Der Besitzer ist sehr sympathisch und hat uns frisches Gemüse gebracht, die Verwalterin ist äusserst zuvorkommend. Für den relatv hohen Preis dürfte das Mobiliar jedoch in einem besseren Zustand sein. Es hat keine bequemen Sessel im Aussenbereich um gemütlich zu sitzen, die sonnenliegen sind etwas gammlig und die Pfannen in der Küche praktisch unbrauchbar zum kochen."
Private Villa with WIFI, private pool, A/C, patio, panoramic view, parking, close to Montepulciano
Villa Ventotto by Paola Orazioli
Pool

Villa Ventotto by Paola Orazioli

9.8 out of 10, Exceptional, (17)
"We had a great time. We stayed for two days"
Villa Ventotto by Paola Orazioli
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (43)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

I Cipressi, 5 bedrooms with pool near Cortona
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Terrace/patio

Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany

9.8 out of 10, Exceptional, (24)
"This property is exactly as we'd imagined it to be! Very charming, great location, beautiful views! Franco and his brother were wonderful. We would definitely stay here again!"
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (10)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
An unforgettable holiday between nature and art. Ideal family friendly location.
Pool

An unforgettable holiday between nature and art. Ideal family friendly location.

10.0 out of 10, Exceptional, (15)
"We stayed here for a family reunion and the villa was absolutely amazing (one member of our group is already looking to come back next year to stay!). Great host, great communication, beautiful property - we would absolutely stay here again next time we're in Italy!"
An unforgettable holiday between nature and art. Ideal family friendly location.
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Pool

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

10.0 out of 10, Exceptional, (37)
"We loved this place! It feels very authentic and it’s so cozy. Would highly recommend to anyone."
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Beautiful villa with spectacular views in a rural location
Outdoor pool

Beautiful villa with spectacular views in a rural location

9.8 out of 10, Exceptional, (40)
"We had a very nice break at a wonderful place with a unique view. We would come back at any time."
Beautiful villa with spectacular views in a rural location
Casale Le Vigne, 8 pax, private pool
Interior

Casale Le Vigne, 8 pax, private pool

10.0 out of 10, Exceptional, (9)
"Group of 9 had a fantastic stay. The villa is superbly fitted out with lovely decor and kitchen equipment. The kids loved the pool as did the adults and the evening meal area was superb. Very good communication with the host who gave us some great suggestions. Loved our holiday and the villa was exactly what we needed. Very secluded so loved watching the stars with lots of local wine."
The price is AED 2,460
AED 2,702 total
includes taxes & fees
15 Jun - 16 Jun
Casale Le Vigne, 8 pax, private pool
Holiday Home La Limonaia - Lovely restored baronial guesthouse
Property grounds

Holiday Home La Limonaia - Lovely restored baronial guesthouse

10.0 out of 10, Exceptional, (35)
"Lovely property with huge garden/grounds.Host was charming and possessed endless helpful information about anything you could wish.We have stayed in many Tuscan rentals in the past but Limonaia is in a different class. We were sad to leave and hope to return.Grazie Mille Arthur and Margreth."
Holiday Home La Limonaia - Lovely restored baronial guesthouse
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
Pool

Villa Uccellaia - Country Villa Rental with swimming pool in Umbria

10.0 out of 10, Exceptional, (66)
"Una location affascinante ed accogliete"
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
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."
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Beautiful private villa with WIFI, private pool, A/C, TV, veranda, panoramic view and parking
Outdoor dining

Beautiful private villa with WIFI, private pool, A/C, TV, veranda, panoramic view and parking

10.0 out of 10, Exceptional, (1)
"A beautiful estate with a stunning view."
Beautiful private villa with WIFI, private pool, A/C, TV, veranda, panoramic view and parking
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

Residenza Fabroni
Lobby

Residenza Fabroni

8.8 out of 10, Excellent, (84)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
Residenza Fabroni
Abbadia Sicille Relais
View from room

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (158)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is AED 501
AED 564 total
includes taxes & fees
21 May - 22 May
Abbadia Sicille Relais
Osteria del Borgo
Standard Room | Exterior

Osteria del Borgo

9.2 out of 10, Wonderful, (144)
"Very nice place to stay to experience Montepulciano. Great location, beautiful restaurant, very nice hospitality "
Osteria del Borgo
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.