A stone building with a window, purple wisteria vines, and potted plants.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Sassicaia Wine Area villas

Exterior

1. Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1 review)
"Tout était impeccable. "
France
Stéphane S.
The price is €130
includes taxes & fees
26 Aug - 27 Aug
Villa Cattleya
Exterior

2. Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano

Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is €164
includes taxes & fees
28 Aug - 29 Aug
Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano
Terrace/patio

3. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Monteverdi Marittimo
The price is €3,583
includes taxes & fees
5 Sept - 6 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Exterior

4. Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi

Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi
Riparbella
10.0 out of 10, Exceptional, (1 review)
"Pros: We enjoyed everything in this house! Great location to visit the region, quiet area but close to points of interest. Fantastic view, the house is surrounded by a great garden. Perfectly renovated by an interior designer. Top quality equipment (bedding, floor AC, electronic appliances) and amenities (beautiful pool, bikes, badminton court). The house is greatly maintained, with an attention to details (welcome bottle of wine, flowers and basic products in the kitchen). Sabina can cook an...
United States
Anonymous traveller
The price is €2,878
includes taxes & fees
18 Sept - 19 Sept
Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi
Exterior detail

5. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Massa Marittima
The price is €510
includes taxes & fees
7 Sept - 8 Sept
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Outdoor dining

6. Villa Ludovica with private pool, Borgo del Silenzio

Villa Ludovica with private pool, Borgo del Silenzio
Lajatico
10.0 out of 10, Exceptional, (1 review)
"Mooie villa met alle accommodatie op een unieke ligging"
Netherlands
Carl P.
Villa Ludovica with private pool, Borgo del Silenzio
Exterior

7. Villa "Cristina" with sea view, private pool and Wi-Fi

Villa "Cristina" with sea view, private pool and Wi-Fi
Riparbella
9.4 out of 10, Exceptional, (10 reviews)
"Pros: The property was clean, very well appointed and had everything we needed. Gian was friendly, very helpful and responded quickly to messages. We would love to come back."
United States
Anonymous traveller
The price is €1,707
includes taxes & fees
22 Sept - 23 Sept
Villa "Cristina" with sea view, private pool and Wi-Fi
Pool

8. AWESHOMEITALY - VILLA SAN MARTINO

AWESHOMEITALY - VILLA SAN MARTINO
La Fornace
The price is €1,260
includes taxes & fees
4 Sept - 5 Sept
AWESHOMEITALY - VILLA SAN MARTINO
Pool

9. Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Chianni
The price is €2,067
includes taxes & fees
10 Sept - 11 Sept
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

10. Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning

Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning
Chioma
The price is €1,688
includes taxes & fees
6 Sept - 7 Sept
Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning
Pool

11. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Gavorrano
The price is €2,744
includes taxes & fees
28 Aug - 29 Aug
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Rooftop pool

12. Villa Tosca

Villa Tosca
Peccioli
The price is €1,233
includes taxes & fees
10 Sept - 11 Sept
Villa Tosca
Pool

13. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is €315
includes taxes & fees
16 Sept - 17 Sept
Villa Le Polle di Meletro
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

Punti Di Vista B&B Food&Wine Experience

Punti Di Vista B&B Food&Wine Experience

10/10 Excellent
"We had an awesome stay at the hotel. The atmosphere was cozy and stylish, and everything was just right. The restaurant really stood out, especially with its amazing food and wine selection—there’s something for everyone, and the choices are seriously impressive. The staff made the experience even better; they were super friendly, helpful, and always on top of things. If you’re after great hospitality and a fantastic meal, this place is definitely worth checking out."
Stephen 1-night trip
Posted 2 weeks ago
Punti Di Vista B&B Food&Wine Experience

Find out more about Sassicaia Wine Area

Sassicaia Wine Area Villas information

Number of reviews
18
Accommodation
36 Villas
Lowest Price
€130
Highest Price
€3,583

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between €130 and €3,583 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 36 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.
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 travelling through Sassicaia Wine Area. If your itinerary includes a trip to Castagneto Carducci, Cavallino Matto is popular with visitors.