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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 ￥26,558
￥37,128 total
includes taxes & fees
Sep 29 - Sep 30
Villa Le Polle di Meletro
A multi-story residential building with a stone wall in front, a balcony on the second floor, and a lit entrance.

2. Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1 review)
"Tout était impeccable. "
France
Stéphane S.
The price is ￥16,216
￥22,702 total
includes taxes & fees
Sep 26 - Sep 27
Villa Cattleya
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

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 ￥436,542
￥479,012 total
includes taxes & fees
Sep 27 - Sep 28
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
A villa with a swimming pool, surrounded by lush greenery and hills.

4. 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 traveler
The price is ￥144,757
￥189,246 total
includes taxes & fees
Oct 1 - Oct 2
Villa "Cristina" with sea view, private pool and Wi-Fi
An outdoor dining area with a table set for four, surrounded by brick pillars and white chairs.

5. 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
A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

6. 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 ￥71,351
￥89,369 total
includes taxes & fees
Oct 19 - Oct 20
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
A stone building with balconies, a gravel path, and a tree.

7. 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 traveler
The price is ￥93,342
￥94,063 total
includes taxes & fees
Oct 7 - Oct 8
Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
A swimming pool with lounge chairs and an umbrella, surrounded by green hills and a clear sky.

8. Ludovica and Marina Villas with 2 pools

Ludovica and Marina Villas with 2 pools
Lajatico
Ludovica and Marina Villas with 2 pools
An outdoor patio with wicker furniture, a sofa, and a table.

9. 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 traveler
The price is ￥875,674
￥876,215 total
includes taxes & fees
Oct 3 - Oct 4
Villa "Tenuta Vallegaia" with sea view, private pool and Wi-Fi
A gazebo with a thatched roof overlooking a scenic landscape.

10. 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.
The price is ￥78,558
￥89,189 total
includes taxes & fees
Oct 17 - Oct 18
Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
A rectangular swimming pool with a stone border, surrounded by lush greenery and tall trees.

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

Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Chianni
The price is ￥304,054
￥338,649 total
includes taxes & fees
Sep 26 - Sep 27
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
A stone house with a garden, a tennis court, and a vineyard in the background.

12. 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 traveler
The price is ￥681,168
￥681,168 total
includes taxes & fees
Sep 27 - Sep 28
Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi
A two-story house with a tiled roof, arched entrance, and a covered patio area.

13. Incredible Villa in the Heart of Tuscany

Incredible Villa in the Heart of Tuscany
Cecina
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Outside pizza oven :)"
Italy
Anonymous traveler
The price is ￥678,422
￥678,963 total
includes taxes & fees
Sep 26 - Sep 27
Incredible Villa in the Heart of Tuscany
A pool with a view of rolling hills and a distant tower.

14. Villa Tosca

Villa Tosca
Peccioli
The price is ￥177,143
￥194,857 total
includes taxes & fees
Sep 28 - Sep 29
Villa Tosca
A clear pool with lounge chairs, a wooden deck, and a view of hills in the background.

15. 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 ￥454,053
￥544,864 total
includes taxes & fees
Sep 27 - Sep 28
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
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

8/10 Good
"."
Asheily 2-night trip
Posted 2 days ago
Relais Sant'Elena

Find out more about Sassicaia Wine Area

Sassicaia Wine Area Villas information

Number of reviews
43
Accommodation
45 Villas
Lowest Price
￥22,702
Highest Price
￥876,215

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between ￥22,702 and ￥876,215 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 45 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.