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

A multi-story residential building with a stone wall in front, a balcony on the second floor, and a lit entrance.

1. Villa Cattleya

Villa Cattleya
Casciana Terme
10.0 out of 10, Exceptional, (1 review)
"Tout était impeccable. "
France
Stéphane S.
The price is AU$208
includes taxes & fees
30 Aug - 31 Aug
Villa Cattleya
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

2. 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 AU$5,835
includes taxes & fees
19 Sept - 20 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
A stone house with a garden, a tennis court, and a vineyard in the background.

3. 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 AU$4,687
includes taxes & fees
19 Sept - 20 Sept
Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi

4. 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 AU$907
includes taxes & fees
8 Sept - 9 Sept
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
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 villa with a swimming pool, surrounded by lush greenery and hills.

6. 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 AU$2,780
includes taxes & fees
17 Sept - 18 Sept
Villa "Cristina" with sea view, private pool and Wi-Fi

7. AWESHOMEITALY - VILLA SAN MARTINO

AWESHOMEITALY - VILLA SAN MARTINO
La Fornace
The price is AU$2,052
includes taxes & fees
4 Sept - 5 Sept
AWESHOMEITALY - VILLA SAN MARTINO
A rectangular swimming pool with a stone border, surrounded by lush greenery and tall trees.

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

Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Chianni
The price is AU$3,366
includes taxes & fees
10 Sept - 11 Sept
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
A covered outdoor dining area with a table and chairs, surrounded by trees and a clear view of the sky.

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

Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning
Chioma
The price is AU$2,749
includes taxes & fees
6 Sept - 7 Sept
Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning
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 AU$4,469
includes taxes & fees
28 Aug - 29 Aug
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
A pool with a view of rolling hills and a distant tower.

11. Villa Tosca

Villa Tosca
Peccioli
The price is AU$2,008
includes taxes & fees
10 Sept - 11 Sept
Villa Tosca
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

12. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is AU$497
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
13
Accommodation
39 Villas
Lowest Price
AU$208
Highest Price
AU$5,835

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
You can expect to pay between AU$208 and AU$5,835 per night for a villa in Sassicaia Wine Area. No matter your budget, the ideal stay is only a click away on Expedia. This price was 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?
Pick from 39 villas in Sassicaia Wine Area. Whether you're holidaying with your family or friends, and wherever your destination, Expedia can help you find the ideal space.
What is there to do near my villa in Sassicaia Wine Area?
Wherever you go in Sassicaia Wine Area, you'll find plenty to keep you entertained here. Spending some time in Castagneto Carducci? Cavallino Matto is a first-rate attraction to include on your itinerary.