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

Sassicaia Wine Area Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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
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
$122 nightly
The price is $137
Oct 29 - Oct 30
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 19 - Oct 20
Total with taxes and fees
Casa Ede: Relax in a Tuscan Village Amid the Beaches and Vineyards of Bolgheri
A historic stone building with multiple windows, a courtyard, and a view of the surrounding village.

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

Apartment "Casina nel Borgo Antico" with Wi-Fi
Bibbona
$89 nightly
The price is $92
Oct 19 - Oct 20
Total with taxes and fees
Apartment "Casina nel Borgo Antico" with Wi-Fi
A compact kitchen with wooden cabinets, a tiled backsplash, a dining table with chairs, and a small decorative item on the wall.

5. Residence le Rose

Residence le Rose
2.0 star property
Bibbona
$80 nightly
The price is $89
Nov 1 - Nov 2
Total with taxes and fees
Residence le Rose
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
$233 nightly
The price is $237
Oct 19 - Oct 20
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
$151 nightly
The price is $155
Oct 19 - Oct 20
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.
$223 nightly
The price is $226
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
$639 nightly
The price is $641
Oct 19 - Oct 20
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
$151 nightly
The price is $155
Oct 19 - Oct 20
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
$213 nightly
The price is $216
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
$218 nightly
The price is $221
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
$218 nightly
The price is $221
Oct 20 - Oct 21
Total with taxes and fees
Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
Private kitchen

14. Via Siena 4 - Suites & Rooms

Via Siena 4 - Suites & Rooms
Cecina
$58 nightly
The price is $67
Oct 19 - Oct 20
Total with taxes and fees
Via Siena 4 - Suites & Rooms
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.

15. 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
$50 nightly
The price is $55
Nov 16 - Nov 17
Total with taxes and fees
Borgo Verde
A reception area with a stone wall, framed pictures, and a view of a swimming pool through a large window.

16. 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
$89 nightly
The price is $102
Oct 25 - Oct 26
Total with taxes and fees
Residenza Santa Cecilia
A beach scene with a clear sky, a sandy shore, and a calm sea.

17. 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
Oleandri Suite Hotel
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 29 - Oct 30
Total with taxes and fees
Poggio all'Agnello – Sport & Active Holidays
A large, circular swimming pool surrounded by lush greenery, with a building featuring a dome and multiple balconies in the background.

19. Relais & Residence Villa Mazzanta

Relais & Residence Villa Mazzanta
3.0 star property
Rosignano Marittimo
9.4 out of 10, Exceptional, (46 reviews)
"The lady at the front desk was very helpful, made some excellent suggestions of things to see during our stay. The room was clean and spacious, and the kitchen well equipped so we could cook some of our own meals."
Canada
Martin
$99 nightly
The price is $109
Oct 25 - Oct 26
Total with taxes and fees
Relais & Residence Villa Mazzanta
A restaurant with white wooden tables and chairs, hanging light bulbs, and green vines.

20. Hotiday Relais Costa degli Etruschi

Hotiday Relais Costa degli Etruschi
Rosignano Marittimo
9.8 out of 10, Exceptional, (9 reviews)
"Struttura bellissima e pulita ambiente tranquillo ideale per staccare dalla routine... Piscina spettacolare con trampolino che i miei figli e noi adulti ci siamo divertiti da matti... E piccolo scivolo ci torneremo Sicuramente..... O"
Italy
Serena
$44 nightly
The price is $48
Nov 16 - Nov 17
Total with taxes and fees
Hotiday Relais Costa degli Etruschi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 3 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.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sassicaia Wine Area vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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 $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sassicaia Wine Area rentals

At Expedia, we put the best Sassicaia Wine Area vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sassicaia Wine Area rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sassicaia Wine Area vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sassicaia Wine Area. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.