Sassicaia Wine Area Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Sassicaia Wine Area vacation rentals

Seasonal outdoor pool
La Rosa dei Venti Resort

Townhouse in Piombino

La Rosa dei Venti Resort
8.4 out of 10, Very Good, (18)
"Amazing location and at an terrific price. Almost too good to be true. "
United States
Mike
La Rosa dei Venti Resort
View from property
Villaggio Miramare

Camping in Livorno

Villaggio Miramare
3.0 star property
8.0 out of 10, Very Good, (52)
"This is such a wonderful place I will definitely return sometime in the future"
United States
Keith
The price is P4,214
P4,773 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villaggio Miramare
Front of property
Domus Socolatae Residenza d'Epoca Charming B&B

Townhouse in Follonica

Domus Socolatae Residenza d'Epoca Charming B&B
9.4 out of 10, Exceptional, (23)
"Our stay was amazing, will be back soon!"
United States
Tiffany
Domus Socolatae Residenza d'Epoca Charming B&B
Living area
Borgo Verde

Apartment in Rosignano Marittimo

Borgo Verde
9.8 out of 10, Exceptional, (43)
"Very nice spacious room at an unbeatable price."
Canada
Dieter
Borgo Verde
Outdoor pool, sun loungers
Borgo degli Olivi

Residence in Piombino

Borgo degli Olivi
3.0 star property
8.2 out of 10, Very Good, (89)
"Nulla da dire ottimo"
Italy
Antonio Pasquale
Borgo degli Olivi
Indoor pool, sun loungers
Residenza Santa Cecilia

Residence in San Vincenzo

Residenza Santa Cecilia
3.0 star property
9.4 out of 10, Exceptional, (39)
"Loved our stay. The room was very spacious and comfortable. Breakfast was delicious and the staff was so kind and helpful. "
United States
Enrique
Residenza Santa Cecilia
Front of property - evening/night
Antico Podere San Francesco Hotel

Vacation Home in Rosignano Marittimo

Antico Podere San Francesco Hotel
9.6 out of 10, Exceptional, (38)
"Very nice property, lovely breakfast and friendly staff!"
United Kingdom
David
Antico Podere San Francesco Hotel
Exterior
Casa in Maremma Tuscany Village

Apartment in Scarlino

Casa in Maremma Tuscany Village
3.0 star property
8.6 out of 10, Excellent, (76)
"Für Hundehalter sehr empfehlenswert"
Switzerland
Johnny
Casa in Maremma Tuscany Village
Exterior
Residence Il Paradiso

Residence in Guardistallo

Residence Il Paradiso
3.0 star property
8.4 out of 10, Very Good, (25)
"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 P5,130
P5,987 total
includes taxes & fees
Dec 30 - Dec 31
Residence Il Paradiso
Exterior
Suites Marilia Apartments

Apartment in Livorno

Suites Marilia Apartments
8.4 out of 10, Very Good, (83)
"I would stay here again. Nice place. Didn’t get to use the pool (December). Had a coin laundry in the car box (parking garage) that was reasonable compared to other places on my travels in Italy. The latte machine in the vending machine area was excellent for 60 cents euro. Great view of the sunset from our massive end unit patio. "
United States
ERIC
The price is P4,720
P5,329 total
includes taxes & fees
Dec 28 - Dec 29
Suites Marilia Apartments
Daily self-serve breakfast (EUR 6 per person)
Beatabb

Aparthotel in Guardistallo

Beatabb
9.0 out of 10, Wonderful, (7)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
Beatabb
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 dei Molini

Relais dei Molini

10/10 Excellent
"We were upgraded to a suite which was great. We were the only guests at the resort and got extra attention. The accommodations and breakfast were next level - we would definitely stay again. Luca was a pleasure to speak with and very knowledgeable."
DOUG 2-night trip
Posted 3 weeks ago
Relais dei Molini

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