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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Sassicaia Wine Area villas

A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

1. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is €189
includes taxes & fees
12 Oct - 13 Oct
Villa Le Polle di Meletro
A villa with a swimming pool, surrounded by lush greenery and hills.

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

Villa "Cristina" with sea view, private pool and Wi-Fi
Riparbella
9.8 out of 10, Exceptional, (12 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 €982
includes taxes & fees
2 Nov - 3 Nov
Villa "Cristina" with sea view, private pool and Wi-Fi
An outdoor patio with wicker furniture, a sofa, and a table.

3. Villa "Tenuta Vallegaia" with sea view, private pool and Wi-Fi

Villa "Tenuta Vallegaia" with sea view, private pool and Wi-Fi
Rosignano Marittimo
8.6 out of 10, Excellent, (4 reviews)
"Pros: Das Haus hat alles was man sich wünscht und ist gut gepflegt."
Germany
Anonymous traveller
The price is €4,953
includes taxes & fees
8 Nov - 9 Nov
Villa "Tenuta Vallegaia" with sea view, private pool and Wi-Fi
A stone house with a garden, a tennis court, and a vineyard in the background.

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 €3,780
includes taxes & fees
11 Oct - 12 Oct
Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi
A stone building with balconies, a gravel path, and a tree.

5. Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi

Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
Follonica
10.0 out of 10, Exceptional, (1 review)
"Pros: La vue proximité mer et ville superbe villa vue sur mer"
France
Anonymous traveller
The price is €428
includes taxes & fees
8 Nov - 9 Nov
Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

6. 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 €2,659
includes taxes & fees
12 Oct - 13 Oct
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
A rectangular swimming pool with a stone border, surrounded by lush greenery and tall trees.

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

Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Chianni
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

8. 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 €476
includes taxes & fees
11 Oct - 12 Oct
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
A wooden deck with a glass enclosure overlooking a mountainous landscape.

9. Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa

Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"It was a very nice vacation at Casa Conti Di Sotto. The VIP area is really private, you only have one neighbour in the other part of the house. The house and garden are well equipped. The main house is located a few meters away from the VIP area. There are all the other things like swimming pool and sauna. The upper part at the sauna has a nice view of the landscape. Vasile was also very nice and helpful."
Germany
Matthias W.
The price is €319
includes taxes & fees
1 Nov - 2 Nov
Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa
A clear pool with lounge chairs, a wooden deck, and a view of hills in the background.

10. 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 €3,024
includes taxes & fees
12 Oct - 13 Oct
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
A gazebo with a thatched roof overlooking a scenic landscape.

11. Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio

Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
Toscana
9.8 out of 10, Exceptional, (21 reviews)
"Posto magnifico, le ville molto curate e pulite, con tutto il necessario e anche di più. La posizione davvero ottima, si arriva in un attimo in paese e in pochi minuti di auto si può raggiungere la costa. Consigliatissimo, sicuramente ritorneremo anche con la bella stagione."
Italy
Giulia O.
Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
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

Tuscan countryhouse apartment, 10 min by the sea, with AC and large garden.

Tuscan countryhouse apartment, 10 min by the sea, with AC and large garden.

10/10 Excellent
"The hosts were extremely accommodating, very friendly and a pleasure to stay next to. I would highly recommend staying here. We had 3 kids who loved the grounds and the dogs. The surrounding area has so much to offer, this was a highlight of our stay in Italy. Thank you!"
Susie S. 4-night trip
Posted 7 days ago
Tuscan countryhouse apartment, 10 min by the sea, with AC and large garden.

Find out more about Sassicaia Wine Area

Sassicaia Wine Area Villas information

Number of reviews
41
Accommodation
42 Villas
Lowest Price
€189
Highest Price
€4,953

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between €189 and €4,953 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 42 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.