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

Holiday Homes in Sassicaia Wine Area

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Sassicaia Wine Area holiday homes

Outdoor dining

Apartment with Garden Steps from La Conchiglia Beach

Apartment with Garden Steps from La Conchiglia Beach
San Vincenzo
The price is NZ$1,699
includes taxes & fees
16 July - 17 July
Apartment with Garden Steps from La Conchiglia Beach
Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas

Fattoria Podere i Luoghi

Fattoria Podere i Luoghi
Casale Marittimo
The price is NZ$160
includes taxes & fees
13 July - 14 July
Fattoria Podere i Luoghi
Marina

Suite in the Ancient Village| House of Febo

Suite in the Ancient Village| House of Febo
Piombino
10.0 out of 10, Exceptional, (1 review)
"Great communication with host. Lovely place and beautiful beach steps away!"
United States
cathleen
The price is NZ$272
includes taxes & fees
1 July - 2 July
Suite in the Ancient Village| House of Febo
Beach nearby

10 minutes from the sea! Apartment with swimming pool and veranda.

10 minutes from the sea! Apartment with swimming pool and veranda.
Toscana
The price is NZ$317
includes taxes & fees
8 July - 9 July
10 minutes from the sea! Apartment with swimming pool and veranda.
Exterior

Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning

Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning
Suvereto
10.0 out of 10, Exceptional, (1 review)
"Pros: Location unica e curata!"
Italy
Anonymous traveller
The price is NZ$257
includes taxes & fees
8 July - 9 July
Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning
Seasonal outdoor pool

San Francesco Country Resort

San Francesco Country Resort
Rosignano Marittimo
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property, lovely breakfast and friendly staff!"
United Kingdom
David
The price is NZ$347
includes taxes & fees
3 July - 4 July
San Francesco Country Resort
Outdoor dining

Tiny Home 'Glamping - La Quercia' with Garden

Tiny Home 'Glamping - La Quercia' with Garden
Monteverdi Marittimo
The price is NZ$279
includes taxes & fees
4 July - 5 July
Tiny Home 'Glamping - La Quercia' with Garden
Outdoor dining

Holiday Home 'Mare Colline Città D'Arte' with Private Garden

Holiday Home 'Mare Colline Città D'Arte' with Private Garden
Rosignano Marittimo
The price is NZ$584
includes taxes & fees
4 July - 5 July
Holiday Home 'Mare Colline Città D'Arte' with Private Garden
Exterior

Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
The price is NZ$438
includes taxes & fees
2 July - 3 July
Podere Cagnesi: Relaxation in nature
Pool

Peaceful Eco House in the Tuscan hills

Peaceful Eco House in the Tuscan hills
casole d'elsa
The price is NZ$402
includes taxes & fees
18 July - 19 July
Peaceful Eco House in the Tuscan hills
Outdoor dining

Casa delle Lumiere. 6 beds between sea, thermal baths, and Tuscan countryside

Casa delle Lumiere. 6 beds between sea, thermal baths, and Tuscan countryside
Lumiere
10.0 out of 10, Exceptional, (2 reviews)
"A very nice house, with great attention to detail in the decoration. Lots of space and well equipped. Looks like the photos and is in good condition, which is probably due to the fact that the owners also live in this house. The only small disadvantage is the proximity to the busy main road, but this is not a problem with air conditioning and closed windows. Defenately a place to come back."
Germany
Felix H.
Casa delle Lumiere. 6 beds between sea, thermal baths, and Tuscan countryside
Beach nearby, sun-loungers

7 HOLIDAY HOUSE RIBOCCHI: TWO-ROOM APARTMENT WITH TERRACE

7 HOLIDAY HOUSE RIBOCCHI: TWO-ROOM APARTMENT WITH TERRACE
Campiglia Marittima
9.4 out of 10, Exceptional, (3 reviews)
"Wohnung super 1. Stock mit großer Terrasse. Lage sehr ruhig und ländlich"
Germany
Alexander F.
The price is NZ$343
includes taxes & fees
5 July - 6 July
7 HOLIDAY HOUSE RIBOCCHI: TWO-ROOM APARTMENT WITH TERRACE
Outdoor dining

Cozy 2-bedroom house in charming Usigliano with breathtaking views

Cozy 2-bedroom house in charming Usigliano with breathtaking views
Usigliano
The price is NZ$339
includes taxes & fees
8 July - 9 July
Cozy 2-bedroom house in charming Usigliano with breathtaking views
Property grounds

Art Beds & Garden 9 beds between the sea, thermal baths, and the Tuscan countrys

Art Beds & Garden 9 beds between the sea, thermal baths, and the Tuscan countrys
Suvereto
Art Beds & Garden 9 beds between the sea, thermal baths, and the Tuscan countrys
Outdoor pool

Farmhouse with swimming pool 2 km away from the sea

Farmhouse with swimming pool 2 km away from the sea
Piombino (LI)
9.8 out of 10, Exceptional, (25 reviews)
"Very silent, very superior garden and also the house,nice big pool,super secure,all was top"
Germany
Yvonne H.
The price is NZ$2,095
includes taxes & fees
8 July - 9 July
Farmhouse with swimming pool 2 km away from the sea
Dining

Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village

Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
Località Gerfalco Montieri
The price is NZ$757
includes taxes & fees
13 July - 14 July
Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
A heated pool

Studio apartment of approximately 20 m2 composed of a living room with kitchenette equipped with 2 induction hobs, small fridge, sink,satellite TV and sofa.Sleeping area separated by sliding door with double bed, bathroom with shower without window.Air c

Studio apartment of approximately 20 m2 composed of a living room with kitchenette equipped with 2 induction hobs, small fridge, sink,satellite TV and sofa.Sleeping area separated by sliding door with double bed, bathroom with shower without window.Air c
Marina di Cecina
8.0 out of 10, Very good, (2 reviews)
"Goed verzorgd, vriendelijk personeel, goed zwembad ,15 minuten lopen naar strand en alle voorzieningen. "
Netherlands
Gerardus R.
Studio apartment of approximately 20 m2 composed of a living room with kitchenette equipped with 2 induction hobs, small fridge, sink,satellite TV and sofa.Sleeping area separated by sliding door with double bed, bathroom with shower without window.Air c
Exterior detail

Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning

Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning
Massa Marittima
The price is NZ$855
includes taxes & fees
8 July - 9 July
Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning
Pool

Apartment 'Podere Nuti - 4 Lauro' with Shared Pool, Garden and Wi-Fi

Apartment 'Podere Nuti - 4 Lauro' with Shared Pool, Garden and Wi-Fi
Cecina
The price is NZ$1,157
includes taxes & fees
2 July - 3 July
Apartment 'Podere Nuti - 4 Lauro' with Shared Pool, Garden and Wi-Fi
Iron/ironing board, WiFi, bed sheets

Bright Studio 50 Meters from the Sea with Wi-Fi and Air Conditioning

Bright Studio 50 Meters from the Sea with Wi-Fi and Air Conditioning
San Vincenzo
The price is NZ$622
includes taxes & fees
3 July - 4 July
Bright Studio 50 Meters from the Sea with 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

10/10 Excellent
"This place is truly heaven on earth. The property is a spectacular private farmhouse nestled in the heart of the Tuscan countryside, offering complete tranquility and breathtaking beauty in every direction. Set in a peaceful valley, it is surrounded by stunning 360-degree views of rolling hills, forests, open fields, and the picturesque town of Bibbona in the distance. It’s a great place to host a wedding or offsite or simply just relax The setting feels timeless; an authentic Tuscan landscape of extraordinary charm and serenity. Whether enjoying a morning coffee overlooking the countryside, swimming in the pool, or simply sunning oneself surrounded by the redolent scent of wildflowers and roses, every moment here is unforgettable. As the sun sets and bathes the hills in golden light, the beauty of the landscape becomes almost magical."
Gitanjali 1-night trip
Posted 3 weeks ago
Relais Sant'Elena

Find out more about Sassicaia Wine Area

Sassicaia Wine Area Holiday Homes information

Number of reviews
34
Accommodation
111 Holiday Homes
Lowest Price
NZ$160
Highest Price
NZ$2,095