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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Sassicaia Wine Area and around

Villa Cresci with pool 5 minutes from spa center
Exterior

Villa Cresci with pool 5 minutes from spa center

Villa Cresci with pool 5 minutes from spa center
Comfortable Tuscany Family House with Private Pool close to beach and wine area
Exterior

Comfortable Tuscany Family House with Private Pool close to beach and wine area

Comfortable Tuscany Family House with Private Pool close to beach and wine area
Villa SIloral, a jewel in the Etruscan Coast
Exterior

Villa SIloral, a jewel in the Etruscan Coast

Villa SIloral, a jewel in the Etruscan Coast
House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach
Terrace/patio

House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach

9.8 out of 10, Exceptional, (19)
"After a busy week in the city, this was the perfect change of pace. The house fit our large family, the walk to the beach was easy, the grounds were manicured and spacious. It was so relaxing. Desi was a fantastic host."
House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach
Villa Palma luxury detached house with direct access to the beach
Terrace/patio

Villa Palma luxury detached house with direct access to the beach

10.0 out of 10, Exceptional, (2)
"Mi chiamo Raina lusuardi ho soggiornato con la Mia famiglia e amici in questa splendida villa , villa Palma , pulitissima chic con spazi ben distribuiti e attrezzati , posizione super con davanti una pineta con accesso al mare strepitosa ! La proprietaria Allegra e’ meravigliosa , disponibile simpatica e ci ha accontentato in tutto Grazie cara Allegra per tutto . Raina Lusuardi"
Villa Palma luxury detached house with direct access to the beach
Stunning private villa for 6 people with WIFI, private pool, TV, panoramic view and parking
Terrace/patio

Stunning private villa for 6 people with WIFI, private pool, TV, panoramic view and parking

9.2 out of 10, Wonderful, (17)
"Wir waren 9 Tage im Poderino und haben die Zeit sehr genossen. Es war alles sehr sauber und die Schlafzimmer haben super frisch gerochen. Die Küche ist eher spartanisch eingerichtet. Leider keine Spülmaschine vorhanden. Normalerweise sind wir 2 - 3 Wochen in der Toskana. Für einen längeren Aufenthalt würden wir das Haus nicht buchen, da uns das Fehlen der Spülmaschine/Waschmaschine und die sehr einfach eingerichtete Küche nicht gefallen. Für eine Woche war es aber okay, da wir nicht viel gekocht...
Stunning private villa for 6 people with WIFI, private pool, TV, panoramic view and parking
Private Villa with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
Exterior

Private Villa with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking

8.0 out of 10, Very good, (1)
"Sehr schöne Lage im Olivenhain etwas versteckt. Schöner Pool"
Private Villa with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
Villa in Bibbona with 2 bedrooms sleeps 4
Exterior

Villa in Bibbona with 2 bedrooms sleeps 4

10.0 out of 10, Exceptional, (1)
"Wir waren als Familie mit 2 Hunden in dem schönen Ferienhaus. Das Ferienhaus entspricht den Bildern, die Lage ist ein Traum. Man ist für sich, das Grundstück ist nicht einsichtbar. Die Entfernung zum Meer, nur wenige Minuten. Der Gastgeber ist sehr freundlich und kümmert sich regelmäßig um die Pflege des Pools."
Villa in Bibbona with 2 bedrooms sleeps 4
Single villa with swimming pool on the Bolgheri wine route.
Pool

Single villa with swimming pool on the Bolgheri wine route.

9.4 out of 10, Exceptional, (3)
"Es war wunderbar. Sind das zweite Mal da gewesen. Alles super gelaufen."
Single villa with swimming pool on the Bolgheri wine route.
Cuccardino - Holiday House with swimming pool
Outdoor dining

Cuccardino - Holiday House with swimming pool

9.8 out of 10, Exceptional, (20)
"Just returned from 2 weeks in this wonderful villa. The villa is just a 2 minute drive from the local village which has restaurants and shops but is set in a beautiful and peaceful location surrounded by olive groves. The views are fantastic and the pool is perfect. Would definitely recommend. Sleeps 4 comfortably and the air conditioning was fantastic at night."
Cuccardino - Holiday House with swimming pool
Cosy apartment in villa for 4 people with WIFI, A/C, pool, TV, patio, pets allowed and parking
Pool

Cosy apartment in villa for 4 people with WIFI, A/C, pool, TV, patio, pets allowed and parking

Cosy apartment in villa for 4 people with WIFI, A/C, pool, TV, patio, pets allowed and parking
Villa Corallina 12, Emma Villas
Exterior

Villa Corallina 12, Emma Villas

Villa Corallina 12, Emma Villas
Casa nel Bosco - independent villa with large fully fenced garden
Outdoor dining

Casa nel Bosco - independent villa with large fully fenced garden

8.0 out of 10, Very good, (1)
"Accoglienza calorosa e precisa,il posto carino anche se non fresco come speravamo. Paesaggio molto piacevole e possibilità di piacevoli passeggiate."
Casa nel Bosco - independent villa with large fully fenced garden
Villa in Castagneto Carducci with 7 bedrooms sleeps 12
Exterior

Villa in Castagneto Carducci with 7 bedrooms sleeps 12

Villa in Castagneto Carducci with 7 bedrooms sleeps 12
Bolgheri Countryhouse
Property grounds

Bolgheri Countryhouse

The price is €552
includes taxes & fees
1 Sept - 2 Sept
Bolgheri Countryhouse
Villa in Marina Di Bibbona with 4 bedrooms sleeps 8
Outdoor dining

Villa in Marina Di Bibbona with 4 bedrooms sleeps 8

Villa in Marina Di Bibbona with 4 bedrooms sleeps 8
Villa La Quercia-Dalia
Outdoor dining

Villa La Quercia-Dalia

Villa La Quercia-Dalia
Wonderful private villa with A/C, private pool, WIFI, TV, terrace, panoramic view and parking
Pool

Wonderful private villa with A/C, private pool, WIFI, TV, terrace, panoramic view and parking

Wonderful private villa with A/C, private pool, WIFI, TV, terrace, panoramic view and parking
Villa Corallina 12
Villa

Villa Corallina 12

Villa Corallina 12
Poderino - House with swimming pool
Exterior

Poderino - House with swimming pool

10.0 out of 10, Exceptional, (11)
"Beautyful area, nice house with a great swimming pool. Friendly owner. Booking is very easy and quick response if you have any questions."
Poderino - House with swimming pool
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 Sassicaia Wine Area Hotel Reviews

Relais Sant'Elena

Relais Sant'Elena

10/10 Excellent
"Relays Sant’Elena was a piece of heaven! Luxurious and beautiful surroundings and caring staff who went above and beyond in every way, allowed for the most relaxing and special stay. I can’t wait to return!"
Patricia 3-night trip
Posted 6 days ago
Relais Sant'Elena

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between €552 and €552 per night. These getaways provide the privacy of your own space at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Sassicaia Wine Area?
Take a look at our 64 villas in Sassicaia Wine Area and then select your favourite. Whether you're planning a family holiday or reuniting with friends, your perfect stay is just a few clicks away with Expedia.
Why book your villa in Sassicaia Wine Area with Expedia?
Reserving a villa in Sassicaia Wine Area is as easy as clicking on your travel dates and selecting a place that satisfies your needs. On the lookout for something luxurious or low cost, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results and find your ideal pad.