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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Villas in Sassicaia Wine Area

Villa Cresci with pool 5 minutes from spa center
Outdoor pool

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
Pool

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
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
Property grounds

country villa with private pool between Bolgheri & Castagneto 5 km from the sea

8.6 out of 10, Excellent, (14)
"Schöne super große Unterkunft auf einem umzäunten Gelände. Pool ist super und ebenfalls umzäunt. Kleine Grillstelle und Outfoorküche die wir immer genutzt haben"
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
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
Outdoor dining

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
Pool

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
Villa in Bibbona with 2 bedrooms sleeps 4
Fridge, microwave, oven, stovetop

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.
Property grounds

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
Pool

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
"Villa Jenny " with swimming pool and WI-FI
Outdoor pool

"Villa Jenny " with swimming pool and WI-FI

"Villa Jenny " with swimming pool and WI-FI
Villa Corallina 12, Emma Villas
Pool

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
Pool

Villa in Castagneto Carducci with 7 bedrooms sleeps 12

Villa in Castagneto Carducci with 7 bedrooms sleeps 12
Bolgheri Countryhouse
Outdoor dining

Bolgheri Countryhouse

Bolgheri Countryhouse
Villa in Marina Di Bibbona with 4 bedrooms sleeps 8
Pool

Villa in Marina Di Bibbona with 4 bedrooms sleeps 8

Villa in Marina Di Bibbona with 4 bedrooms sleeps 8
Villa La Quercia-Dalia
Beach nearby

Villa La Quercia-Dalia

Villa La Quercia-Dalia
Villa Corallina 12
Villa

Villa Corallina 12

Villa Corallina 12
Poderino - House with swimming pool
Terrace/patio

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
Villa Cresci - Villa del Lodano
Outdoor dining

Villa Cresci - Villa del Lodano

Villa Cresci - Villa del Lodano
Villa in Marina Di Bibbona with 6 bedrooms sleeps 12
Property grounds

Villa in Marina Di Bibbona with 6 bedrooms sleeps 12

Villa in Marina Di Bibbona with 6 bedrooms sleeps 12
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 3 weeks ago
Relais Sant'Elena

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
You can expect to pay between and per night for a villa in Sassicaia Wine Area. No matter your budget, the ideal stay is only a click away on Expedia. This price was 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?
Pick from 54 villas in Sassicaia Wine Area. Whether you're holidaying with your family or friends, and wherever your destination, Expedia can help you find the ideal space.
What is there to do near my villa in Sassicaia Wine Area?
Wherever you go in Sassicaia Wine Area, you'll find plenty to keep you entertained here. Spending some time in Castagneto Carducci? Cavallino Matto is a first-rate attraction to include on your itinerary.