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

GLAMPING PIAN DELLE GINESTRE

GLAMPING PIAN DELLE GINESTRE
Sassetta
The price is P8,283
P9,460 total
includes taxes & fees
Jun 29 - Jun 30
GLAMPING PIAN DELLE GINESTRE

Hotel Campo Di Carlo

Hotel Campo Di Carlo
Sassetta
9.8 out of 10, Exceptional, (6 reviews)
"Ci siamo fermati una Notte! Personale gentilissimo tutto perfetto ci ritorneremo fermandoci per più giorni e provare la piscina e le Terme nelle vicinanze"
Italy
antonio
The price is P11,824
P13,146 total
includes taxes & fees
Jul 4 - Jul 5
Hotel Campo Di Carlo

Villaggio Miramare

Villaggio Miramare
3.0 star property
Livorno
8.0 out of 10, Very Good, (54 reviews)
"Fantastic place to stay!"
United Kingdom
Victoria
The price is P8,557
P9,691 total
includes taxes & fees
Jul 5 - Jul 6
Villaggio Miramare

Room Rent Morrona

Room Rent Morrona
Terricciola
9.0 out of 10, Wonderful, (6 reviews)
"Ottima struttura "
Italy
Marzia
The price is P4,620
P5,083 total
includes taxes & fees
Jun 29 - Jun 30
Room Rent Morrona

La Rosa dei Venti Resort

La Rosa dei Venti Resort
Piombino
8.4 out of 10, Very Good, (18 reviews)
"Amazing location and at an terrific price. Almost too good to be true. "
United States
Mike
The price is P10,537
P11,800 total
includes taxes & fees
Jun 28 - Jun 29
La Rosa dei Venti Resort

Borgo degli Olivi

Borgo degli Olivi
3.0 star property
Piombino
8.2 out of 10, Very Good, (89 reviews)
"Nulla da dire ottimo"
Italy
Antonio Pasquale
The price is P10,458
P11,783 total
includes taxes & fees
Jun 30 - Jul 1
Borgo degli Olivi

Borgo Verde

Borgo Verde
Rosignano Marittimo
9.8 out of 10, Exceptional, (51 reviews)
"Parking on site. Beautiful apartment next to beach, shopping center, dinning and everything you may need."
United States
Luisa
The price is P5,191
P5,849 total
includes taxes & fees
Jun 29 - Jun 30
Borgo Verde

Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (2 reviews)
"Ótimo local, limpo, amplo, piscina boa, cascata boa, espaço amplo, adorei o local."
Brazil
Alan Cesar
The price is P4,613
P5,562 total
includes taxes & fees
Jul 19 - Jul 20
Podere Cascatelle & Agriletizia

Poggio all'Agnello – Sport & Active Holidays

Poggio all'Agnello – Sport & Active Holidays
3.0 star property
Populonia Stazione
8.4 out of 10, Very Good, (104 reviews)
"We were as a family of 5 and stayed very comfortably. "
Italy
Ufuk
The price is P9,641
P10,883 total
includes taxes & fees
Jul 9 - Jul 10
Poggio all'Agnello – Sport & Active Holidays

Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very Good, (26 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 P4,543
P4,997 total
includes taxes & fees
Jul 6 - Jul 7
Residence Il Paradiso

Casa Vacanze Dolce Vita

Casa Vacanze Dolce Vita
2.0 star property
Campiglia Marittima
9.0 out of 10, Wonderful, (8 reviews)
"The place was lovely and probably more so in the spring or in summer. We visited as we had business in town. The place was beautiful however location wise it is best suited for those with cars as there are no restaurants or shops nearby. Transportation is ok but bus intervals are usually 1hr apart. As for the bus stop it is right outside Dolce Vita but it's pitch black dark at night and dangerous so be careful. I would recommend you to rent a car when staying here."
Philippines
Francesca
The price is P8,897
P15,789 total
includes taxes & fees
Jul 2 - Jul 3
Casa Vacanze Dolce Vita

Hotel Residence Stella del Mare

Hotel Residence Stella del Mare
3.0 star property
Rosignano Marittimo
8.0 out of 10, Very Good, (92 reviews)
"Friendly staff. Nice hotel for some relaxing days by the pool. "
Sweden
Anonymous traveler
The price is P9,137
P10,260 total
includes taxes & fees
Jun 29 - Jun 30
Hotel Residence Stella del Mare

San Francesco Country Resort

San Francesco Country Resort
Rosignano Marittimo
9.6 out of 10, Exceptional, (45 reviews)
"Very nice property, lovely breakfast and friendly staff!"
United Kingdom
David
The price is P7,219
P8,080 total
includes taxes & fees
Jun 29 - Jun 30
San Francesco Country Resort

Oleandri Suite Hotel

Oleandri Suite Hotel
2.0 star property
Rosignano Marittimo
9.4 out of 10, Exceptional, (19 reviews)
"Great hotel friendly staff "
United Kingdom
Riadh
The price is P12,492
P13,951 total
includes taxes & fees
Jul 6 - Jul 7
Oleandri Suite Hotel

Suites Marilia Apartments

Suites Marilia Apartments
Livorno
8.6 out of 10, Excellent, (87 reviews)
"QQQ"
Germany
Ober
The price is P6,446
P7,369 total
includes taxes & fees
Jun 29 - Jun 30
Suites Marilia Apartments

Casa Elena - Vista Mare & Parcheggio

Casa Elena - Vista Mare & Parcheggio
San Vincenzo
2.0 out of 10, (1 review)
"Un esperienza mai provata prima!! Terribile!! Arrivati, sembrava tutto ok..poi entro in camera e il letto era sdifatto! Qualcuno ci aveva dormito .. asciugamani usati gettati a terra! Anche in bagno stessa cosa.. ascigamani usati sporcizia! La casa praticamente non era stata pulita! Panico!!! Cerco di contatatre tramite la app..ma niente, nessuna risposta! Era gia sera. Impossibile trovare un altra soluzione..quindi sono dovuta andare a comprare lenzuoli, asciugamani e pulire io!!! Che...
Italy
Rosalba
The price is P2,979
P9,029 total
includes taxes & fees
Jul 7 - Jul 8
Casa Elena - Vista Mare & Parcheggio

Residenza Santa Cecilia

Residenza Santa Cecilia
3.0 star property
San Vincenzo
9.6 out of 10, Exceptional, (45 reviews)
"Great place"
United Kingdom
jeffrey
The price is P13,591
P15,194 total
includes taxes & fees
Jul 15 - Jul 16
Residenza Santa Cecilia

Relais & Residence Villa Mazzanta

Relais & Residence Villa Mazzanta
3.0 star property
Rosignano Marittimo
9.2 out of 10, Wonderful, (36 reviews)
"Great location, beautiful pool, good breakfast options. Only negative would be that the rooms smelled somewhat damp. "
Canada
Anita
The price is P14,467
P16,123 total
includes taxes & fees
Jun 29 - Jun 30
Relais & Residence Villa Mazzanta

Fattoria Palazzeta Pet & Family Friendly

Fattoria Palazzeta Pet & Family Friendly
Cecina
10.0 out of 10, Exceptional, (1 review)
"The property was great: spacious, very nicely decorated and a big fenced garden for our dog to play. Very friendly staff who helped with our needs including extremely late check-out. "
Netherlands
Marijn
The price is P34,035
P39,044 total
includes taxes & fees
Jun 28 - Jun 29
Fattoria Palazzeta Pet & Family Friendly

Podere San Giuseppe

Podere San Giuseppe
San Vincenzo
9.0 out of 10, Wonderful, (16 reviews)
"Great place, with good facilities, and communication. Will definitely return."
Italy
Anonymous traveler
The price is P7,878
P8,840 total
includes taxes & fees
Jun 28 - Jun 29
Podere San Giuseppe
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

Search for holiday rentals in Sassicaia Wine Area on Expedia! You can easily find your home rentals, villas, holiday apartments in Sassicaia Wine Area using one of the methods below:

  • View our selection of featured holiday rentals in Sassicaia Wine Area
  • Use the map to find apartments and other holiday homes in the Sassicaia Wine Area neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sassicaia Wine Area while they last

Look no further and take a look at our great range of rental properties in Sassicaia Wine Area!