Villas in Sassicaia Wine Area

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Sassicaia Wine Area villas

Property grounds
VILLA BOLGHERI - Six Bedroom Villa, Sleeps 14

Villa in Castagneto Carducci

$2,494 nightly
The price is $2,494
Jan 1 - Jan 2, 2026
Total with taxes and fees
VILLA BOLGHERI - Six Bedroom Villa, Sleeps 14
Exterior
Villa Cattleya

Villa in Casciana Terme

10.0 out of 10, Exceptional, (1)
"Tout était impeccable. "
France
Stéphane S.
$158 nightly
The price is $158
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Cattleya
Interior
Superb "Tuscan"-style cottage situated on a hill, welcomes families

Villa in Crespina Lorenzana

$264 nightly
The price is $311
Dec 11 - Dec 12
Total with taxes and fees
Superb "Tuscan"-style cottage situated on a hill, welcomes families
Pool
Villa Altea - Homelike Villas

Villa in Lajatico

10.0 out of 10, Exceptional, (1)
"Wir hatten eine wunderschöne Woche in einem tollen Haus und mit einem sehr aufmerksamen Gastgeber, danke Riccardo! Die Kommunikation mit der Agentur (Home Villas) war unterirdisch!!! Auf keine Email kam eine Reaktion, außer dass man sich melden würde. Wir wollten vorab einige Dinge abklären (Anzahl der Personen hatte sich reduziert, wäre früherer Check In möglich, etc.), selbst das vorzeitige Anmelden aller Personen mit Ausweisen wurde nicht an den Vermieter weitergeleitet!! Vor Ort gab es...
Germany
Stephan H.
Villa Altea - Homelike Villas
Exterior
CASTELLO LEOPOLDO - Twelve Bedroom Villa, Sleeps 28

Villa in Campiglia Marittima

$4,433 nightly
The price is $4,433
Jan 3 - Jan 4, 2026
Total with taxes and fees
CASTELLO LEOPOLDO - Twelve Bedroom Villa, Sleeps 28
Pool
VILLA POETA - Six Bedroom Villa, Sleeps 12

Villa in Campiglia Marittima

$2,078 nightly
The price is $2,078
Dec 20 - Dec 21
Total with taxes and fees
VILLA POETA - Six Bedroom Villa, Sleeps 12
Pool
Villa Fiordaliso - Homelike Villas

Villa in Lajatico

Villa Fiordaliso - Homelike Villas
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 dei Molini

Relais dei Molini

10/10 Excellent
"We were upgraded to a suite which was great. We were the only guests at the resort and got extra attention. The accommodations and breakfast were next level - we would definitely stay again. Luca was a pleasure to speak with and very knowledgeable."
DOUG 2-night trip
Posted 8 days ago
Relais dei Molini

Find out more about Sassicaia Wine Area

Sassicaia Wine Area Villas information

Number of reviews
1
Accommodation
54 Villas
Lowest Price
$158
Highest Price
$4,433

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between $158 and $4,433 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 54 villas in Sassicaia Wine Area and then select your favorite. Whether you're planning a family vacation 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.
How can I find cheap villas in Sassicaia Wine Area?
Expedia can help you track down cheap villas in Sassicaia Wine Area. Simply use the filter tool to select amenities, budget and star rating to refine your search and find an awesome place to stay in a few quick clicks.
What is there to do near my villa in Sassicaia Wine Area?
You'll find many attractions to explore when traveling through Sassicaia Wine Area. If your itinerary includes a trip to Castagneto Carducci, Cavallino Matto is popular with visitors.

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