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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 NZ$246
includes taxes & fees
26 Aug - 27 Aug
Villa Cattleya
Terrace/patio

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 NZ$6,999
includes taxes & fees
10 Sept - 11 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Exterior

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 NZ$5,622
includes taxes & fees
1 Sept - 2 Sept
Villa 'Le Sughere' with Sea View, Pool, Terrace and Wi-Fi
Exterior detail

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
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Outdoor dining

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
Exterior

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 NZ$3,049
includes taxes & fees
23 Sept - 24 Sept
Villa "Cristina" with sea view, private pool and Wi-Fi
Seasonal outdoor pool

7. AWESHOMEITALY - VILLA SAN MARTINO

AWESHOMEITALY - VILLA SAN MARTINO
La Fornace
The price is NZ$2,465
includes taxes & fees
4 Sept - 5 Sept
AWESHOMEITALY - VILLA SAN MARTINO
Pool

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 NZ$4,038
includes taxes & fees
10 Sept - 11 Sept
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

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 NZ$3,298
includes taxes & fees
6 Sept - 7 Sept
Villa 'Magnolie' with Sea View, Private Garden and Air Conditioning
Pool

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 NZ$5,369
includes taxes & fees
28 Aug - 29 Aug
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Seasonal outdoor pool, pool umbrellas, pool loungers

11. Villa Tosca

Villa Tosca
Peccioli
The price is NZ$2,408
includes taxes & fees
10 Sept - 11 Sept
Villa Tosca
Pool

12. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
The price is NZ$597
includes taxes & fees
20 Sept - 21 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
NZ$246
Highest Price
NZ$6,999

Frequently asked questions

How much do villas in Sassicaia Wine Area cost?
Villas in Sassicaia Wine Area range between NZ$246 and NZ$6,999 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 39 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.
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.