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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Sassicaia Wine Area vacation rentals

Comfort Studio

1. Residence le Rose

Residence le Rose
2.0 star property
Bibbona
$127 nightly
The price is $143
Aug 28 - Aug 29
Total with taxes and fees
Residence le Rose
Outdoor pool

2. 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
$118 nightly
The price is $132
Aug 23 - Aug 24
Total with taxes and fees
Hotel Campo Di Carlo
Exterior

3. 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
$127 nightly
The price is $142
Aug 31 - Sep 1
Total with taxes and fees
GLAMPING PIAN DELLE GINESTRE
Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

4. 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
$99 nightly
The price is $109
Aug 30 - Aug 31
Total with taxes and fees
Residence Il Paradiso
Pool

5. Residenza Santa Cecilia

Residenza Santa Cecilia
3.0 star property
San Vincenzo
9.4 out of 10, Exceptional, (49 reviews)
"Great place"
United Kingdom
jeffrey
$203 nightly
The price is $228
Sep 20 - Sep 21
Total with taxes and fees
Residenza Santa Cecilia
Pool

6. 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
$797 nightly
The price is $880
Aug 28 - Aug 29
Total with taxes and fees
Fattoria Palazzeta Pet & Family Friendly
Apartment, 1 Bedroom, Tower | View from room

7. Podere San Giuseppe

Podere San Giuseppe
San Vincenzo
9.2 out of 10, Wonderful, (17 reviews)
"Great place, with good facilities, and communication. Will definitely return."
Italy
Anonymous traveler
$187 nightly
The price is $208
Aug 30 - Aug 31
Total with taxes and fees
Podere San Giuseppe
Breakfast area

8. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (18 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
$85 nightly
The price is $93
Sep 20 - Sep 21
Total with taxes and fees
Beatabb
Villa, 2 Bedrooms, Garden Area | Living area

9. Borgo Verde

Borgo Verde
Rosignano Marittimo
9.8 out of 10, Exceptional, (56 reviews)
"I had a wonderful stay! Everything was exceptionally clean, comfortable, and cozy, making it easy to relax. The staff were incredibly kind, friendly, and always ready to help with a smile. Their hospitality made the experience even more enjoyable. The atmosphere was warm and welcoming, and I truly felt at home. I highly recommend this place and would be happy to stay here again in the future!"
Germany
Elena
$51 nightly
The price is $58
Sep 20 - Sep 21
Total with taxes and fees
Borgo Verde
Aerial view

10. Relais & Residence Villa Mazzanta

Relais & Residence Villa Mazzanta
3.0 star property
Rosignano Marittimo
9.2 out of 10, Wonderful, (40 reviews)
"Great location, beautiful pool, good breakfast options. Only negative would be that the rooms smelled somewhat damp. "
Canada
Anita
$161 nightly
The price is $181
Aug 23 - Aug 24
Total with taxes and fees
Relais & Residence Villa Mazzanta
Outdoor pool

11. Borgo Guglielmo

Borgo Guglielmo
Cecina
9.0 out of 10, Wonderful, (18 reviews)
"Very nice apartment. Great pool and nice and service minded staff. We were very satisfied with our stay. "
Norway
Ingunn S
$82 nightly
The price is $93
Sep 13 - Sep 14
Total with taxes and fees
Borgo Guglielmo
Beach

12. Oleandri Suite Hotel

Oleandri Suite Hotel
2.0 star property
Rosignano Marittimo
9.4 out of 10, Exceptional, (22 reviews)
"Clean nice room, everything is working fine but not beachfront !"
United Kingdom
Hossam
$103 nightly
The price is $117
Sep 20 - Sep 21
Total with taxes and fees
Oleandri Suite Hotel
Spa

13. 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
$169 nightly
The price is $189
Aug 30 - Aug 31
Total with taxes and fees
Casa Vacanze Dolce Vita
Outdoor pool

14. Hotel Residence Stella del Mare

Hotel Residence Stella del Mare
3.0 star property
Rosignano Marittimo
8.0 out of 10, Very Good, (98 reviews)
"Friendly staff. Nice hotel for some relaxing days by the pool. "
Sweden
Anonymous traveler
$97 nightly
The price is $111
Sep 21 - Sep 22
Total with taxes and fees
Hotel Residence Stella del Mare
Bar (on property)

15. Poggio all'Agnello – Sport & Active Holidays

Poggio all'Agnello – Sport & Active Holidays
3.0 star property
Populonia Stazione
8.6 out of 10, Excellent, (111 reviews)
"We were as a family of 5 and stayed very comfortably. "
Italy
Ufuk
$103 nightly
The price is $117
Sep 20 - Sep 21
Total with taxes and fees
Poggio all'Agnello – Sport & Active Holidays
Pool

16. La Cecinella

La Cecinella
3.0 star property
Cecina
7.0 out of 10, Good, (38 reviews)
"Die Anlage und deren Konzept super, aber die Häuser würden eine Renovierung ertragen. "
Switzerland
Alexandra
$110 nightly
The price is $124
Sep 21 - Sep 22
Total with taxes and fees
La Cecinella
Apartment, 1 Bedroom | Private kitchen

17. Cav Costa degli Etruschi

Cav Costa degli Etruschi
San Vincenzo
9.2 out of 10, Wonderful, (20 reviews)
"Alles zu Fuß gut erreichbar Zentrum und Strand In der Nähe ein pizzabäcker und eine bar Top Lage sehr nette ihnhaber die jeden Tag bis mittags erreichbar sind und einen immer helfen. Einrichtung im typischen italienischen Style, was aber sehr sauber war. Wir würden dort wieder buchen."
Germany
Giuseppe
$83 nightly
The price is $95
Sep 22 - Sep 23
Total with taxes and fees
Cav Costa degli Etruschi
Outdoor pool

18. Borgo degli Olivi

Borgo degli Olivi
3.0 star property
Piombino
8.2 out of 10, Very Good, (91 reviews)
"Very quiet and relaxing location. Nice garden and pool. Friendly staff. Room was good but slightly outdated."
Germany
martin
$123 nightly
The price is $140
Sep 20 - Sep 21
Total with taxes and fees
Borgo degli Olivi
Rooftop pool

19. San Francesco Country Resort

San Francesco Country Resort
Rosignano Marittimo
9.4 out of 10, Exceptional, (50 reviews)
"The property comes off as a resort type hotel with great stuff. But it’s more like a large family camp ground on an olive farm with a swimming pool."
Canada
Kamaljit
$108 nightly
The price is $122
Sep 11 - Sep 12
Total with taxes and fees
San Francesco Country Resort
Restaurant

20. Hotiday Relais Costa degli Etruschi

Hotiday Relais Costa degli Etruschi
Rosignano Marittimo
9.8 out of 10, Exceptional, (7 reviews)
"Geweldige locatie, super personeel, geweldig zwembad, auto parkeren was prima, kort bij het strand, goede airco in de kamers dus kortom helemaal niks te klagen."
Netherlands
Egon
$85 nightly
The price is $96
Sep 20 - Sep 21
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

Punti Di Vista B&B Food&Wine Experience

Punti Di Vista B&B Food&Wine Experience

10/10 Excellent
"We had an awesome stay at the hotel. The atmosphere was cozy and stylish, and everything was just right. The restaurant really stood out, especially with its amazing food and wine selection—there’s something for everyone, and the choices are seriously impressive. The staff made the experience even better; they were super friendly, helpful, and always on top of things. If you’re after great hospitality and a fantastic meal, this place is definitely worth checking out."
Stephen 1-night trip
Posted 11 days ago
Punti Di Vista B&B Food&Wine Experience

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 $142 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.