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

Sassicaia Wine Area Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sassicaia Wine Area vacation rentals

1. Casa Ede: Relaxation in a Tuscan village nestled between the beaches and vineyards of Bolgheri

Casa Ede: Relaxation in a Tuscan village nestled between the beaches and vineyards of Bolgheri
Bibbona
The price is CA $113
CA $146 total
includes taxes & fees
Nov 12 - Nov 13
Casa Ede: Relaxation in a Tuscan village nestled between the beaches and vineyards of Bolgheri

2. 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
The price is CA $212
CA $218 total
includes taxes & fees
Nov 9 - Nov 10
Il Vicolo Spacious Room in the Village – Experience Village Charm with Style

3. 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
The price is CA $212
CA $218 total
includes taxes & fees
Nov 9 - Nov 10
Camera Il Paese with Double Panoramic View – Stay in the Village with Charm

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

Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is CA $287
CA $311 total
includes taxes & fees
Nov 10 - Nov 11
Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning

5. 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.
The price is CA $294
CA $318 total
includes taxes & fees
Nov 11 - Nov 12
Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning

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

Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is CA $280
CA $304 total
includes taxes & fees
Nov 15 - Nov 16
Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning

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

Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning
Bibbona
The price is CA $287
CA $311 total
includes taxes & fees
Nov 15 - Nov 16
Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning

8. Residenza Santa Cecilia

Residenza Santa Cecilia
3.0 star property
San Vincenzo
9.6 out of 10, Exceptional, (52 reviews)
"Great place"
United Kingdom
jeffrey
The price is CA $96
CA $105 total
includes taxes & fees
Dec 9 - Dec 10
Residenza Santa Cecilia

9. Borgo Verde

Borgo Verde
Rosignano Marittimo
9.8 out of 10, Exceptional, (61 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
The price is CA $71
CA $79 total
includes taxes & fees
Dec 9 - Dec 10
Borgo Verde

10. Cav Costa degli Etruschi

Cav Costa degli Etruschi
San Vincenzo
9.4 out of 10, Exceptional, (21 reviews)
"Easy walk to restaurants."
United States
Eduardo
The price is CA $99
CA $109 total
includes taxes & fees
Nov 10 - Nov 11
Cav Costa degli Etruschi

11. Hotiday Relais Costa degli Etruschi

Hotiday Relais Costa degli Etruschi
Rosignano Marittimo
9.8 out of 10, Exceptional, (9 reviews)
"An amazing little gem in Tuscany. Beautiful scenery, tranquil and very relaxed feeling. Would definitely recommend and visit again."
United Kingdom
Ant
The price is CA $75
CA $83 total
includes taxes & fees
Nov 15 - Nov 16
Hotiday Relais Costa degli Etruschi

12. 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
The price is CA $143
CA $165 total
includes taxes & fees
Nov 14 - Nov 15
Residence Il Paradiso

13. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"Beautiful B&B! Clean, comfortable room & wonderful breakfast "
United States
Joanne
The price is CA $105
CA $115 total
includes taxes & fees
Nov 9 - Nov 10
Beatabb

14. Via Siena 4 - Suites & Rooms

Via Siena 4 - Suites & Rooms
Cecina
The price is CA $93
CA $102 total
includes taxes & fees
Nov 30 - Dec 1
Via Siena 4 - Suites & Rooms

15. Studio apartment 50 meters from the beach.

Studio apartment 50 meters from the beach.
San Vincenzo
8.8 out of 10, Excellent, (3 reviews)
"Unkomplizierter Vermieter. Saubere Wohnung schöne Wohnung. Gute Lage. Für lärmempfindliche (schlafen) wegen Strasse und Zug... dann TOP :)"
Germany
Thomas E.
The price is CA $94
CA $206 total
includes taxes & fees
Nov 14 - Nov 15
Studio apartment 50 meters from the beach.

16. Three-bedroom apartment 50 meters from the beach.

Three-bedroom apartment 50 meters from the beach.
San Vincenzo
9.2 out of 10, Wonderful, (7 reviews)
"Appartamento spazioso e funzionale, vista mare e zona centrale, mobilio raffinato e pulito, disponibilità di tutte le comodità accessorie nel vano cucina e camere da letto. Grazioso balconcino relax e soleggiato. "
Italy
Luana
The price is CA $126
CA $271 total
includes taxes & fees
Nov 9 - Nov 10
Three-bedroom apartment 50 meters from the beach.

17. La Rosa dei Venti Resort

La Rosa dei Venti Resort
Piombino
8.2 out of 10, Very good, (20 reviews)
"Amazing location and at an terrific price. Almost too good to be true. "
United States
Mike
The price is CA $171
CA $188 total
includes taxes & fees
Nov 16 - Nov 17
La Rosa dei Venti Resort

18. 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 CA $134
CA $179 total
includes taxes & fees
Nov 9 - Nov 10
Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning

19. San Francesco Country Resort

San Francesco Country Resort
Rosignano Marittimo
9.4 out of 10, Exceptional, (55 reviews)
"Loved the resort and excellent service."
United Kingdom
PIETRO
The price is CA $120
CA $132 total
includes taxes & fees
Dec 7 - Dec 8
San Francesco Country Resort

20. La Ripadoro

La Ripadoro
Chianni
10.0 out of 10, Exceptional, (2 reviews)
"Amazing place Amazing view Amazing food Amazing people. Highly recommended."
Canada
Maya
The price is CA $227
CA $265 total
includes taxes & fees
Nov 17 - Nov 18
La Ripadoro
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sassicaia Wine Area Hotel Reviews

Find out more about Sassicaia Wine Area

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sassicaia Wine Area. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.