Search Villas in Sassicaia Wine Area

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Villas in Sassicaia Wine Area and around

Our top choices for Sassicaia Wine Area villas

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
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 SIloral, a jewel in the Etruscan Coast
Exterior

Villa SIloral, a jewel in the Etruscan Coast

Villa SIloral, a jewel in the Etruscan Coast
Private Villa with private pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, parking
Fridge, microwave, oven, stovetop

Private Villa with private pool, WIFI, A/C, 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 private pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, parking
Beautiful private villa for 6 guests with WIFI, private pool, TV, panoramic view and parking
Terrace/patio

Beautiful private villa for 6 guests with WIFI, private pool, TV, panoramic view and parking

9.2 out of 10, Wonderful, (18)
"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...
Beautiful private villa for 6 guests with WIFI, private pool, TV, panoramic view and parking
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
Lovely apartment in villa for 4 guests with WIFI, A/C, pool, TV, patio, pets allowed and parking
Pool

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

Lovely apartment in villa for 4 guests with WIFI, A/C, pool, TV, patio, pets allowed and parking
Villa La Quercia-Dalia
Beach nearby

Villa La Quercia-Dalia

Villa La Quercia-Dalia
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

The price is €493
includes taxes & fees
2 Sept - 3 Sept
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 Corallina 12
Villa

Villa Corallina 12

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

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

Stunning private villa with WIFI, A/C, private pool, TV, terrace, panoramic view and parking
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?
Villas in Sassicaia Wine Area range between €493 and €493 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.