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

Sassicaia Wine Area Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Sassicaia Wine Area vacation rentals

A modern outdoor lounge area with a curved white bench, surrounded by lush greenery and two wooden cabins with slanted roofs.

1. 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
$114 nightly
The price is $127
Nov 2 - Nov 3
Total with taxes and fees
GLAMPING PIAN DELLE GINESTRE
A sunset over a beach with a large piece of driftwood.

2. Residence le Rose

Residence le Rose
2.0 star property
Bibbona
Residence le Rose
A reception area with a stone wall, framed pictures, and a view of a swimming pool through a large window.

3. 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
$79 nightly
The price is $87
Nov 1 - Nov 2
Total with taxes and fees
Residenza Santa Cecilia
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.

4. 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
$45 nightly
The price is $50
Nov 18 - Nov 19
Total with taxes and fees
Borgo Verde
A restaurant with white wooden tables and chairs, hanging light bulbs, and green vines.

5. 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
$45 nightly
The price is $49
Dec 1 - Dec 2
Total with taxes and fees
Hotiday Relais Costa degli Etruschi
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

6. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"Beautiful B&B! Clean, comfortable room & wonderful breakfast "
United States
Joanne
$71 nightly
The price is $78
Dec 1 - Dec 2
Total with taxes and fees
Beatabb
A compact kitchen with a dining area, featuring a round table, chairs, a built-in oven, and a TV mounted on the wall.

7. 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
$68 nightly
The price is $75
Nov 26 - Nov 27
Total with taxes and fees
Cav Costa degli Etruschi
A building with a stucco exterior, multiple windows, and a tiled roof.

8. 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
$90 nightly
The price is $99
Nov 20 - Nov 21
Total with taxes and fees
Residence Il Paradiso
A view through a window with a view of a landscape and a body of water.

9. 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
$53 nightly
The price is $58
Nov 1 - Nov 2
Total with taxes and fees
Podere San Giuseppe
Beach

10. Via Siena 4 - Suites & Rooms

Via Siena 4 - Suites & Rooms
Cecina
$52 nightly
The price is $57
Nov 3 - Nov 4
Total with taxes and fees
Via Siena 4 - Suites & Rooms
A beach with clear turquoise water, two wooden picnic tables, and a sandy shore with trees in the background.

11. Fattoria Podere i Luoghi

Fattoria Podere i Luoghi
Casale Marittimo
$70 nightly
The price is $82
Nov 1 - Nov 2
Total with taxes and fees
Fattoria Podere i Luoghi
A pool area with lounge chairs and a thatched umbrella, surrounded by a fence and greenery.

12. 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
$272 nightly
The price is $299
Nov 8 - Nov 9
Total with taxes and fees
Fattoria Palazzeta Pet & Family Friendly
A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

13. Villa Le Polle di Meletro

Villa Le Polle di Meletro
Rivalto
$192 nightly
The price is $211
Nov 1 - Nov 2
Total with taxes and fees
Villa Le Polle di Meletro
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and a building with large windows.

14. 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
$84 nightly
The price is $92
Nov 24 - Nov 25
Total with taxes and fees
San Francesco Country Resort
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a hedge.

15. Hotiday Apartments Costa degli Etruschi

Hotiday Apartments Costa degli Etruschi
Rosignano Marittimo
$40 nightly
The price is $44
Dec 1 - Dec 2
Total with taxes and fees
Hotiday Apartments Costa degli Etruschi
An open dining area with a table set for two, a red sofa, and a painting on the wall.

16. La Ripadoro

La Ripadoro
Chianni
10.0 out of 10, Exceptional, (1 review)
"Amazing place Amazing view Amazing food Amazing people. Highly recommended."
Canada
Maya
$161 nightly
The price is $177
Nov 3 - Nov 4
Total with taxes and fees
La Ripadoro
A rooftop swimming pool with a view of the sea and hills during sunset.

17. La Rosa dei Venti Resort

La Rosa dei Venti Resort
Piombino
8.2 out of 10, Very good, (20 reviews)
"The location is beautiful right on top of the cliff over watching the ocean in the islands. A nice path going down to the beach. Also, there is a pool that can be used. This place is more rooms to rent than the hotel. There is no room service and the rooms are not equipped Well to eat in or just relax inside."
United States
Rafael
$119 nightly
The price is $131
Nov 1 - Nov 2
Total with taxes and fees
La Rosa dei Venti Resort
A kitchen with exposed brick walls, a modern white cabinet, and a built-in black oven.

18. Room Rent Morrona

Room Rent Morrona
Terricciola
9.2 out of 10, Wonderful, (7 reviews)
"Ottima struttura "
Italy
Marzia
$74 nightly
The price is $81
Nov 1 - Nov 2
Total with taxes and fees
Room Rent Morrona
A person relaxing in a hot tub with a glass of wine.

19. Botrona B&B

Botrona B&B
Scarlino
9.4 out of 10, Exceptional, (26 reviews)
"Amazing B&B! Beautiful, clean, and very classy! Staff is excellent and friendly… breakfast is superb and staff’s hospitality is heart warming. Our stay was very pleasant. Home away from home… surprisingly beautiful grounds with jacuzzi and a sauna available whenever you want! Thank you!"
United States
Anna
$80 nightly
The price is $88
Nov 1 - Nov 2
Total with taxes and fees
Botrona B&B
A rectangular pool with a waterfall feature, surrounded by lounge chairs and potted plants.

20. Hotel Residence Stella del Mare

Hotel Residence Stella del Mare
3.0 star property
Rosignano Marittimo
8.0 out of 10, Very good, (101 reviews)
"Friendly staff. Nice hotel for some relaxing days by the pool. "
Sweden
Anonymous traveler
$499 nightly
The price is $549
Nov 15 - Nov 16
Total with taxes and fees
Hotel Residence Stella del Mare
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

Historic Tuscan House with Private Panoramic Garden Medieval Bibbona, Near Sea

Historic Tuscan House with Private Panoramic Garden Medieval Bibbona, Near Sea

10/10 Excellent
"Beautiful town and great place to stay. The outdoor space was exceptional."
Jennifer N. 7-night trip
Posted 2 weeks ago
Historic Tuscan House with Private Panoramic Garden Medieval Bibbona, Near Sea

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 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.