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

Sassicaia Wine Area Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Sassicaia Wine Area vacation rentals

A beach with rows of striped beach chairs and yellow umbrellas.

1. Camping Casa di Caccia

Camping Casa di Caccia
2.0 star property
Bibbona
9.0 out of 10, Wonderful, (7 reviews)
"Ruhiger gemütlicher Campingplatz"
Germany
Rene
$86 nightly
The price is $96
Oct 15 - Oct 16
Total with taxes and fees
Camping Casa di Caccia
A modern outdoor lounge area with a curved white bench, surrounded by lush greenery and two wooden cabins with slanted roofs.

2. GLAMPING PIAN DELLE GINESTRE

GLAMPING PIAN DELLE GINESTRE
Sassetta
10.0 out of 10, Exceptional, (1 review)
"Wir waren mit der Unterkunft sehr zufrieden. Die Inhaber waren sehr freundlich und fürsorglich. Es ist eine familiäre und ruhige Atmosphäre. Das Frühstück war wirklich toll. Am Anreisetag wurde uns sogar extra etwas zum Essen vorbereitet, obwohl die Küche geschlossen war. Auch für Hunde ist es ein Traum. Wir würden jederzeit wieder dort buchen, dann aber aufgrund der Temperaturen im Zelt eher im Herbst."
Germany
Jan
$123 nightly
The price is $138
Oct 22 - Oct 23
Total with taxes and fees
GLAMPING PIAN DELLE GINESTRE
A modern kitchen with a central island, built-in appliances, and a window with an open door.

3. Casa Ede: Relax in a Tuscan Village Amid the Beaches and Vineyards of Bolgheri

Casa Ede: Relax in a Tuscan Village Amid the Beaches and Vineyards of Bolgheri
Bibbona
$112 nightly
The price is $112
Oct 16 - Oct 17
Total with taxes and fees
Casa Ede: Relax in a Tuscan Village Amid the Beaches and Vineyards of Bolgheri
A compact kitchen with wooden cabinets, a tiled backsplash, a dining table with chairs, and a small decorative item on the wall.

4. Residence le Rose

Residence le Rose
2.0 star property
Bibbona
$80 nightly
The price is $88
Nov 1 - Nov 2
Total with taxes and fees
Residence le Rose
A historic stone building with multiple windows, a courtyard, and a view of the surrounding village.

5. Apartment "Casina nel Borgo Antico" with Wi-Fi

Apartment "Casina nel Borgo Antico" with Wi-Fi
Bibbona
$88 nightly
The price is $92
Oct 16 - Oct 17
Total with taxes and fees
Apartment "Casina nel Borgo Antico" with Wi-Fi
A swimming pool with red and white striped umbrellas, surrounded by lounge chairs and trees.

6. Casa Vacanze Heidi Apartment with Shared Pool and Private Terrace

Casa Vacanze Heidi Apartment with Shared Pool and Private Terrace
Marina di Bibbona
$232 nightly
The price is $235
Oct 16 - Oct 17
Total with taxes and fees
Casa Vacanze Heidi Apartment with Shared Pool and Private Terrace
A two-story building with a central entrance, a staircase leading to the upper floor, and a small balcony with a railing.

7. Il Vicolo Spacious Room in the Village – Experience Village Charm with Style

Il Vicolo Spacious Room in the Village – Experience Village Charm with Style
Castagneto Carducci
$158 nightly
The price is $163
Oct 21 - Oct 22
Total with taxes and fees
Il Vicolo Spacious Room in the Village – Experience Village Charm with Style
An aerial view of a property with a swimming pool, multiple buildings, and well-maintained gardens.

8. Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
10.0 out of 10, Exceptional, (1 review)
"Kleines mobile Home mit allem was man braucht.Terrasse ist supi. Zum Pool sind es ca 100m.Pool ist sauber und groß genug zum schwimmen, hat allerdings nur von 10-19 Uhr auf. Ruhige Umgebung. Man ist schnell im Hinterland mit Bergen und Wasserfällen oder am Meer. Für alle was dabei. Gerne wieder "
Germany
Michael W.
$222 nightly
The price is $225
Oct 19 - Oct 20
Total with taxes and fees
Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning
A garden with a gravel path, various shrubs, and trees.

9. Apartment with Garden Steps from La Conchiglia Beach

Apartment with Garden Steps from La Conchiglia Beach
San Vincenzo
$635 nightly
The price is $638
Oct 16 - Oct 17
Total with taxes and fees
Apartment with Garden Steps from La Conchiglia Beach
A room with a dining area, a large mirror, and a laptop on a table.

10. Camera Il Paese with Double Panoramic View – Stay in the Village with Charm

Camera Il Paese with Double Panoramic View – Stay in the Village with Charm
Castagneto Carducci
$158 nightly
The price is $163
Oct 21 - Oct 22
Total with taxes and fees
Camera Il Paese with Double Panoramic View – Stay in the Village with Charm
An aerial view of a property with a swimming pool, multiple buildings, and well-maintained gardens.

11. Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
$212 nightly
The price is $215
Oct 19 - Oct 20
Total with taxes and fees
Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning
An aerial view of a property with a swimming pool, multiple buildings, and well-maintained gardens.

12. Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
$217 nightly
The price is $220
Oct 19 - Oct 20
Total with taxes and fees
Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning
An aerial view of a property with a swimming pool, multiple buildings, and well-maintained gardens.

13. Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning

Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
$217 nightly
The price is $220
Oct 19 - Oct 20
Total with taxes and fees
Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
A large, circular swimming pool surrounded by lush greenery, with a building featuring a dome and multiple balconies in the background.

14. Relais & Residence Villa Mazzanta

Relais & Residence Villa Mazzanta
3.0 star property
Rosignano Marittimo
9.2 out of 10, Wonderful, (45 reviews)
"Great location, beautiful pool, good breakfast options. Only negative would be that the rooms smelled somewhat damp. "
Canada
Anita
$98 nightly
The price is $108
Oct 25 - Oct 26
Total with taxes and fees
Relais & Residence Villa Mazzanta
A reception area with a stone wall, framed pictures, and a view of a swimming pool through a large window.

15. Residenza Santa Cecilia

Residenza Santa Cecilia
3.0 star property
San Vincenzo
9.6 out of 10, Exceptional, (51 reviews)
"Great place"
United Kingdom
jeffrey
$84 nightly
The price is $97
Oct 28 - Oct 29
Total with taxes and fees
Residenza Santa Cecilia
A beach scene with a clear sky, a sandy shore, and a calm sea.

16. Oleandri Suite Hotel

Oleandri Suite Hotel
2.0 star property
Rosignano Marittimo
9.6 out of 10, Exceptional, (24 reviews)
"Great hotel friendly staff "
United Kingdom
Riadh
$88 nightly
The price is $97
Oct 17 - Oct 18
Total with taxes and fees
Oleandri Suite Hotel
A modern living room with a sofa, a wooden table, and a dining area with white chairs. There are hanging lights and a view of greenery outside.

17. Borgo Verde

Borgo Verde
Rosignano Marittimo
9.8 out of 10, Exceptional, (60 reviews)
"Absolutely LOVED our stay at this property and didn’t want to leave! The apartment was bigger than expected, and had everything we could ask for. The grounds are so beautiful and the pool was wonderful. Highly recommend and hope to return for an extended stay on my next trip to Italy!"
United States
Laura
$52 nightly
The price is $57
Oct 18 - Oct 19
Total with taxes and fees
Borgo Verde
A table with two drinks, a bowl of snacks, and a decorative shell on a balcony overlooking a pool.

18. Poggio all'Agnello – Sport & Active Holidays

Poggio all'Agnello – Sport & Active Holidays
3.0 star property
Populonia Stazione
8.6 out of 10, Excellent, (116 reviews)
"We were as a family of 5 and stayed very comfortably. "
Italy
Ufuk
$89 nightly
The price is $98
Oct 18 - Oct 19
Total with taxes and fees
Poggio all'Agnello – Sport & Active Holidays
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

19. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
$73 nightly
The price is $80
Oct 22 - Oct 23
Total with taxes and fees
Beatabb
A building with a stucco exterior, multiple windows, and a tiled roof.

20. Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (27 reviews)
"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"
Germany
Jason
$73 nightly
The price is $80
Oct 15 - Oct 16
Total with taxes and fees
Residence Il Paradiso
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

Tombolo Talasso & Beach Resort

Tombolo Talasso & Beach Resort

10/10 Excellent
"Incroyable resort,superbe plage et Spa magnifique"
Manon 1-night trip
Posted 2 weeks ago
Tombolo Talasso & Beach Resort

Find out more about Sassicaia Wine Area

Everything you need to know about Sassicaia Wine Area vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sassicaia Wine Area vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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Sassicaia Wine Area vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sassicaia Wine Area. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sassicaia Wine Area in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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